I grew up in the 80s. This was an exceptionally complicated time for movies as Hollywood had just spent over a decade giving carte blanche to directors and artists so they could expand budgets, bloat their creativity, and leverage the Reagan-inspired obsession with money and status. These firmly-implanted mores are now part of our everyday lexicon, unnoticed by anyone under the age of 30, and lamented by those old enough to remember that free thought was once celebrated rather than derided. The average human’s side-tracking with self-indulgence and “me” culture is rooted in the 80s, and the stench of social media and online influencing was first belched forth into the ether during this moment in history. Movie studios were licking their wounds from the mistakes made from the Heaven’s Gate fiasco, and simultaneously there was the root of cancel culture and censorship slowly beginning to rear its ugly head. It’s only been in the past decade that erasing people from having a voice has become such a rage, but silencing the voices of dissenting angles because they deviate from the popular opinion is a yankee tradition more rich than baseball or the flag itself.
I mention these 80s tropes because you’re going to see a lot of 80s comedies on this list. I was born in the 70s, and I think most people tend to gravitate toward film that was made during that very impressionable time of our youth where we’re figuring out who we are, what we like, and what’s acceptable, both socially and personally. You’re not going to see a lot of movies pre-70s because frankly, I don’t think old movies are all that funny. Sure, if I grew up watching Charlie Chaplain movies I’d include everything he ever did in this list, but I don’t watch his movies and thus, don’t care to add them here because there’s an expectation that I do. By the reverse of that same token of psychology, you’re not going to see a lot of modern films on this list. Comedies in our current age of ultra woke-ism, racial check-listing, gender over-acknowledgment, and virtue signaling are amongst the most offensively boring and tired sacks of crap that this earth has ever devised. As I live through this droning tale of social fakery, I patiently await the current chapter of creative canceling to be firmly shut forever, never to be revisited.
As I was devising this list, I looked up other top comedy collections on the interwebs, and I noticed a pattern: there seems to be a general understanding of what comedies should be on a “best of” list. However, I don’t see many people just relaxing and choosing from their personal favorites. In fact, I don’t see any. What I see is a lot of copying and pasting, plentiful woke-ness, and stinky generalizations of what comedies are now acceptable in this bloated age of political-correctness and socially acceptable “comedy”. Well, I say, fuck that. I’m going to talk about the best 100 comedies I’ve ever seen and it’s as simple as that. I’ll give you my painfully linear take as I view them through my distorted world lens, and you can keep your lame-ass “Bridesmaids” and “Hangover” inclusions to your fuckin’ selves. For those generically-modified sugar farts masquerading as comedies can’t hold a melted candle to these fine films I’m going to discuss at length, and nothing you can say that is altered by the current wet-panty culture can make me think any differently. Enjoy!
100. Life (1999) Directed by Ted Demme
Somehow, “Life” has escaped the viewing of many a person. And that’s a crying shame. Coming out at the end of the 90s, there was a glut of “feel-good” PG-rated comedies starting to permeate theaters, marking the beginning of a depressing trend that still carries over today more than 20 years later. This film got lost in the shuffle, partly because of its R rating, but also because Eddie Murphy was in a considerable downswing with his career trajectory. For those of us who paid attention, we were rewarded with one of the funniest comedies of the 90s. Murphy and Martin Lawrence play a couple of dudes who get mistaken for someone else, and have to pay for it with the heftiest price of all. The chemistry with these two is absolutely fantastic, and Murphy gives one of the greatest performances in his career. An unexpected warmness to the story makes it hard to forget, and the love between the two leads takes it beyond standard buddy comedy fare. The supporting cast of Bernie Mac, Ned Beatty, and R. Lee Ermey doesn’t hurt, but make no mistake about it, Murphy is the true star of this vehicle. “Life” is definitely a film that needs to be rediscovered.
Best line: “Stab ya, choke ya, bite ya….I mean, whatever it takes to make a motherfucker stop existin’, I will do that.”
99. Clear History (2013) Directed by Greg Mottola
Not quite as brilliant as “Curb Your Enthusiasm”, but every bit as funny and goofy, and stretched to 90 minutes. You might think this much time with Larry David is far too much, and you’d have a point. Luckily, Larry surrounds himself with insane talent to bring something hilarious to each and every scene in the film. This is basically an extended episode of “Curb”, but so what? When you’ve got a stellar cast of talent as great as this, it only proves there’s a joke waiting behind every corner, waiting to be unearthed with each successive viewing. The movie is basically a revenge tale on the surface, but make no mistake about it, all of the involved players are on top of their comedic game, making sure there isn’t a single wasted second on screen.
Best line: “If anyone was blowing Chicago that night, it was you.”
98. What About Bob? (1991) Directed by Frank Oz
As most movies directed by Frank Oz, there is a glorious underpinning of menace that dwells inside “What About Bob?”. I didn’t quite like this movie when I first saw it, but after repeated viewings I began to realize the darkness of where it was coming from. Bill Murray’s Bob is a needy, whiny, pathetic, manipulating shithead that is only outdone by the conniving, arrogant, cut-off, and distant Dr. Marvin (played by Richard Dreyfuss). Neither of these guys are particularly endearing, and it’s only Marvin’s emotionally captive family that can offer any relief as they use Bob to communicate with the coldness of Dr. Marvin. Bob is as much an empty vessel as Marvin is a raging jerk. You’re not supposed to like these guys, and that’s the beauty of it. Stories abound of how Murray tortured Dreyfuss on set, irritating him and staying in character as much as possible. It only served to make Dreyfuss more believable, and by the end of the film, you realize that they both deserve what they get. Oz is a master in bringing out the worst in people, and with “What About Bob” he allows us in to laugh at them.
Best line: “Death Therapy, Bob. It’s a guaranteed cure.”
97. Three O’Clock High (1987) Directed by Phil Joanou
While the vast majority of kids in the 80s were pining away for the next John Hughes movie, “Three O’Clock High” came and went without much fanfare. Director Phil Joanou had mostly directed music videos, and cinematographer Barry Sonnenfeld was quietly building a resume of some of the most vividly-created originality in visuals that anyone had seen. This movie probably proved too odd for the generic movie-goer to enjoy, but “Three O’Clock High” came as a blast of fresh air to this 15-year old (at the time). It’s a high school comedy on the surface, but elements of absurdism, sexuality, eroticism, and pure hilarity are all exposed to be the true drive. Kids and adults are all portrayed as numbed and dumb, exposing a societal truism through the lens of Sonnenfeld’s groundbreaking camera work. The comedy isn’t obvious — it depends on a level of intelligence from its audience which generally meant very few people saw it. I’ve seen this film probably 100 times in my life, and something new exposes itself with each viewing.
Best line: “Whoever did this should be plucked out of our school like a burgeoning cancerous growth deep inside the colon.”
96. Ruthless People (1986) Directed by Abrahams and Zucker
The Zucker Brothers and Abrahams shifted gears from their zany Mad Magazine-style gags and made a more straight forward comedy with “Ruthless People”. To try and explain the plot would be trivial as it gets pretty complicated, but suffice it to say this film doesn’t contain a single dull moment. The cast of Danny DeVito, Judge Reinhold, and Helen Slater ensure some serious energy keeps the sotry properly propelled, but make no mistake about it — this movie belongs to Bette Midler. She’s absolutely hilarious in every scene she graces, and easily paces the movie with her acting and sense of timing. The movie could have easily faltered in the hands of a lesser actor, but Midler destroys every line she has, and her energy single-handedly steps up the game of everyone else around her. Easily one of the best performances in a comedy you’ll ever see.
Best line: “Muffy, meet Adolf. Adolf….EAT MUFFY.”
95. Real Genius (1985) Directed by Martha Coolidge
“Real Genius” is the moment we all became aware of Val Kilmer, and for good reason, but the real magic this movie gave us was a look into the politics of college, and jockeying for position. The moral of the story is people over numbers, and that is oddly something that has gone by the wayside ever since. Kilmer is pretty damn funny in the lead role, and his supporting cast is more than worthy, particularly William Atherton, who seemed to be born to play smug entitled assholes in every movie he was ever in. It’s also the first movie to ever include “Everybody Wants To Rule The World” in its soundtrack, which seems like a groundbreaking move in itself.
Best line: “If there is anything I can ever do for you, or, more to the point — to you — you let me know, alright?”
94. Just One Of the Guys (1985) Directed by Lisa Gottlieb
Those of you who grew up in the 80s and had HBO, you’ll know this movie by heart — it was pretty much “The Beastmaster”, “The Hitcher”, and “Just One Of The Guys” on perpetual repeat. Not that there’s anything wrong with that as these are some of the most entertaining films you’ll ever see in their respective genres. The general agenda of this movie is to point out sexism and reflect it back on society, and it works to a point. However, “Just One Of The Guys” works as a pretty damn funny high school comedy in its own right. William Zabka is here as the bully he was born to play, but the real scene stealing crown belongs to Billy Jacoby as the younger brother of the heroine, Terri. The film does a pretty respectful job of exposing gender roles and expectations, but it’s the pussy and dick jokes that keep it special.
Best line: “I’ve had plenty of sex. It’s just that now, I’d like to try it with a partner.”
93. Fletch (1985) Directed by Michael Ritchie
You can dislike Chevy Chase all you want, and that’s fair; he’s an unlikeable asshole in real life. However, that doesn’t disguise the fact that he’s an insanely talented comedic performer. “Fletch” isn’t the funniest movie Chase has ever been in (keep scrolling down for those), but this is way up there. Director Michael Ritchie was no stranger to comedy at the time, and he was smart enough to just get out the way and let Chase own the role. “Fletch” really pops with energy and originality, and it has managed to stay fresh after all of these years. The supporting players are all on top of their game, and Chase just dominates a character that he seems to understand at every level. Smart, sneaky, biting, witty, funny…Fletch is Chevy Chase to the very core.
Best line: “Excuse you?”
92. Midnight Run (1988) Directed by Martin Brest
“Midnight Run” has a little of everything in it, but one can’t deny the hilarious chemistry between Robert De Niro and Charles Grodin. Sometimes a movie rises above the sum of its parts thanks to these types of phenomena, and the talented Martin Brest was able to take a slightly lame story and transcend it into a vehicle to show off some tremendous acting talent. Joe Pantoliano, Dennis Farina, Yaphet Kotto, John Ashton, and Philip Baker Hall all show up to help us forget the goofiness of the plot, and they do it with aplomb. But it’s De Niro and Grodin that give us something to remember. You really feel like these guys grow to love each other, and their performances aren’t just hilarious, but touching and deep to boot.
Best line: “I can’t even argue with you — I don’t know what the fuck you’re talking about.”
91. Get Shorty (1995) Directed by Barry Sonnenfeld
Yes, I have two Dennis Farina movies in a row here, and why not? He somehow manages to be the funniest part of “Get Shorty”, which is no mean feat when you consider the cast. Sonnenfeld does a stellar job of presenting a comedy with enough tension and violence that it’s sometimes hard to make out what exactly it is. By the end of film, it turns out to be a cynical indictment of the movie industry with inventive camera work and tons of laughs to help buoy the intensity. Sonnenfeld shows off his immense talent in capturing sarcasm in all of its gnarly splendor.
Best line: “They say the fuckin’ smog is the fuckin’ reason you have such beautiful fuckin’ sunsets”.
90. Weird Science (1985) Directed by John Hughes
Many kids in the 80s eagerly anticipated each new John Hughes movie with bated breath, but I was not one of them. I generally found Hughes films to be overwrought, cheesy, and funny on a very generic level as to appeal to the widest possible audience. There’s nothing inherently wrong with that, but it meant that a lot of his films just didn’t pack a comedic punch that resonated. Hughes films are typically remembered for some life lesson learned, or some pat happy ending, or all of the problems of the characters involved being solved to the point of saccharine obnoxiousness. “Weird Science” works because of its madcap absurdity. It does have those irritating Hughes moments where the characters overcome a challenge and the cornball music swells in the background trying to illicit some phony sentiment, but for the most part, “Weird Science” is only interested in being as offensive as it can be. It sometimes falters because of its tendency to wink at the camera, but for the most part, this is a very funny movie that has stood the test of time. Bill Paxton steals the show as Chet; in fact, the movie’s biggest weakness is the lack of him in it.
Best line: “I didn’t think it was a whale’s dick, honey.”
89. Jackass (2002-2022)
I’m not sure what can actually be said about the Jackass movies that can’t be watched, other than this: you’ve got to be checked out of life to not laugh at these films. They tend to go on a bit longer than we’d like, and there’s only so much self-abuse one can take before it starts getting a little boring. But there are few franchises that I can remember that elicit such an exciting response when word spreads there’s a new installment on the horizon. For the same reasons the Three Stooges were beloved back in their day, the Jackass dudes have updated the finger-in-the-eye schtick for the 21st century. Just sit back, and enjoy what these knuckleheads do to themselves in order to entertain us.
88. The Brady Bunch movies (1995-1996) Directed by Betty Thomas and Arlene Sanford
I never thought I’d be extolling the hilarious virtues of a Brady Bunch movie in an all-time-best comedy list, but dammit, here I am doing it. What these movies do so well is take our affection for the original TV series, and mock all of the things that made no sense about it in the first place. There are no nods to the audience, it’s just a cast of actors taking the material seriously enough where we feel like an idiotic family such as this might actually exist somewhere. They refuse to change, which is a refreshing take on a society that is perpetually obsessed with the past and constantly trying to recreate it. Gary Cole’s version of Mike Brady is absolutely hilarious, but it’s Marcia and Jan’s relationship that make these films soar. You might think you’ll hate these films, but try them out anyway — you might be pleasantly surprised.
Best line: A gift is only a good thing when the giver has given thought to that gift. But when the gift the giver gives gives grief, then that gift should give the givee regrets.
87. White Men Can’t Jump (1992) Directed by Ron Shelton
Easily one of the funniest sports movies ever made, it also happens to be just a flat-out hilarious comedy of any genre tag. The energy of Woody Harrelson and Wesley Snipes is impossible to turn off, and Shelton’s love and knowledge of sports makes the film work at fundamental level. Rosie Perez steals the show in limited scenes she appears in, but what makes this film work lies in its ability to walk away from its subject matter in a real and mature way rather than force a pat and satisfying conclusion down out throats. What doesn’t hurt are the athletic abilities of the two leads, particularly Harreslon — these dudes can play basketball!
86. Dirty Work (1998) Directed Bob Saget
How Artie Lange out-survived both Norm MacDonald AND Bob Saget is anyone’s guess, but that discussion is for another time. This movie could have been even better if not for clueless movie-goers being too dim to understand the breadth of Macdonald’s sense of humor, and movie executives’ inability to grasp the magic of wonderful R-rated comedy, so when “Dirty Work” released in 1998, it suffered cuts and general disinterest. Despite the movie being dumbed down to lengths where generic SNL-watching audiences wouldn’t be offended, the film still shone as a ridiculous absurdist comedy with just enough raunch to make it hilarious. The late-90s saw a lot of people turn on Norm, but the ones who were smart enough to recognize his genius were gifted a pretty damn funny movie thanks to some awesome support from Artie Lange, Chirs Farley, Chevy Chase, and Don Rickles, while Bob Saget showed off his eye for comedic detail with his shrewd direction. “Dirty Work” came out at a time where the vast majority of comedies were feel-good PG-rated bubble gum garbage, and audiences were beginning their senseless tirade against anything that wasn’t presentable to immature audiences who were too dim to appreciate humor that wasn’t a moronic rom-com — something that is in full force and accepted as the norm today. For the rest of the comedy-loving public who love humor that we could never come up with ourselves, “Dirty Work” shimmers as a shining beam of creativity.
Best line: “Son of a bitch bastard!“
85. Step Brothers (2008) Directed by Adam McKay
Will someone please tell Adam McKay to go back to making comedies? Because his dramas are terrible. “Step Brothers” is the kind of movie that, when you describe it to someone else, you say, “it’s fucking hilarious, dude”. The movie shouldn’t work. Failure is set up every step of the way. The story is dumb. It’s not particularly well-written. And somehow, amidst all of these facts, the movie triumphs because of the fantastic performances of everyone in it. Will Ferrell and John C. Reilly are great of course, but there isn’t a single supporting role around them that isn’t laugh out loud funny. There are just too many great lines in “Step Brothers” to pick as a favorite, and this movie works brilliantly because of the chemistry of all of its actors.
Best line: “You ever fuck so much you had to put your dick in the freezer?“
84. Animal House (1978) Directed By John Landis
I know I’ll take shit for putting this so low on the list, but just hear me out for a minute. I simply never thought this movie was that great. Yes, I understand what it did for comedy. Yes, I know how influential it was, and still is. But truth is, the film was never that great as a comedy in its day, and it has certainly not aged well on top of it. “Animal House” is a testament in how films can change landscapes — I appreciate and recognize this acutely. But this film is hard to like. It’s not even in the top five movies John Landis ever directed, much less the greatest comedy ever made (keep scrolling down for Landis’ best films). There are literally no likable characters in this entire film, and it spawned dozens of absolutely terrible high school/college comedies that have always sucked hard. (“Porky’s”, anyone?) So as much as I appreciate how this film skewed minds and altered perspectives, the fact remains that it’s really not at all as funny as the vast majority give it credit for. The one thing it does bring us is the genius of Landis, who would use this film as a springboard to immediately begin producing some of the greatest films ever made, not just in the comedy genre, but across the board.
Best line: “Zero….point….ZERO.”
83. Ghostbusters (1984) Directed by Ivan Reitman
As I trudge forth with this list, I also recognize “Ghostbusters” as an overrated comedy. I have accepted that I don’t see something that others see in terms of how this movie holds up over the years, but I will say that, when I saw this film in the theater for my 12th birthday in the summer of 1984, my little mind was throughly entertained from start to finish. What I loved most about it then, and continue to love to this day, are the delicate dramatic scenes sprinkled within the comedy — the scene where Dan Aykroyd and Ernie Hudson are talking about the end of the world in the Ghostmobile spring to mind. The film is ultimately a vehicle for Bill Murray to be a smart ass for the most part, but the real charm of the movie comes from the other characters who surround him. Sigourney Weaver is funny in her role as an 80’s-style Regan, and Rick Moranis absolutely owns every scene he’s in. But It’s Aykroyd and Harold Ramis that the movie needs more of. Murray’s smarminess actually stands in the way of making this film truly great, but it’s an entertaining zeitgeist of American culture all the same.
Best line: “I collect spores, mold, and fungus.”
82. The Apartment (1960) Directed by Billy Wilder
Hot on the heels of “Some Like It Hot”, Billy Wilder and Jack Lemmon figured they should quickly return with the comedy magic they had harnessed and unleashed on the world. Wilder was beginning to head into the twilight of his career, where Lemmon was smack dab in the middle of his prime (in terms of being a huge bankable star — he would only get greater as an actor). “The Apartment” is all about Wilder keeping the camera squarely focused on Lemmon, and the film is a marvel because of it. You can’t take your eyes off of Lemmon as he owns every microsecond.
Best line: “Shut up and deal.”
81. Strange Brew (1983) Directed by Rick Moranis and Dave Thomas
As I was adding this to my list of great comedies, I thought, is this a guilty pleasure? Turns out, I don’t care if it is or isn’t — I feel confident in what I feel is a great comedy, and this absolutely should be included. And let me tell you, when you’re an 11-year old boy, there is no greater film in existence to commit to and connect with than “Strange Brew”. The silliness, the intelligence, the great acting, the writing, the appearance of Mel Blanc….it simply is all here. Max Von Sydow popping up as the villain is a great touch as well, but it’s Moranis and Thomas showcasing their wit that exalts this film into classic status. It’s aged very well, too. It has plenty of weirdness and darkness to supplant the film in some netherworld sci-fi territory, and it’s always anchored by completely lovable absurdism. As an American, it might be unfair to compare this Canadian treasure to another Great White North comedy team known as “Trailer Park Boys”, but “Strange Brew” is definitely a spiritual successor. A comedy that needs to be discovered by everyone.
Best line: “I didn’t fart, it was the chair, eh!”
80. 48 Hours (1982) Directed by Walter Hill
“48 Hours” is the first film I’ll add to the list that tows the line between hilariousness and balls-out intensity. This film is bleeding with both, and there’s an argument to be made that it created a certain genre while still being the best in its class. While undoubtedly being an extremely intense crime adventure, it’s also funny as all hell, and the working relationship between Eddie Murphy and Nick Nolte is one of the best ever put to screen. One has to wonder how improvised Murphy’s performance was, and while he’s splashing his creativity all over the filmic canvas, Nolte is right there keeping up with him as the slightly-out-of-touch older guy. “48 Hours” also takes up a very rare space in movie history where it could get away with violating social norms, and expose the hypocrisies that exist in racism and sexism within popular culture as we are inundated with these archaic concepts in the present day. It’s an extremely intelligent movie that will surely outsmart the majority of social justice warriors that stink up the landscape in 2023. As commonplace as buddy cop movies are now, they simply didn’t exist back in the early 80s, and “48 Hours” was not only the seedling for it all, but also the greatest example of it.
Best line: “Bullshit; you’re too fucking stupid to have a job.”
79. The Toxic Avenger (1984) Directed by Lloyd Kaufman
As a 12-year old boy in 1984, I’m not sure I was more impressed with any other superhero than I was with The Toxic Avenger. Toxy represented everything I wanted to be: a fighter of evil, a self-less protector, a powerful brawler, and a classy pussy magnet. To do all of this while wearing a tutu was just the radioactive cherry on top of the desiccated cake. This movie took all of the elements of an underground sex comedy and seamlessly mixed it with a gory horror flick, producing a highly satisfying result. The bad guys are truly abhorrent scumbags as well, bringing some real shock value and justification for Toxy to kill them off in such horrific fashion. The voiceover of Toxy is worth the price of admission alone. It’s cheaply made and it’s not for everyone, but the ones who do love it treat it with the reverence it so justly deserves.
Best line: “Do you think I look inconspicuous enough?”
78. Splash (1984) Directed by Ron Howard
“Splash” was one of those comedic experiences where I learned the power of seeing a film with a rapturous audience. People who never saw a movie in the theater in the 80s might have a hard time understanding how much funnier a film could be while everyone around you is laughing their asses off. Each time I watch this film I get taken back to energy I felt around me as the audience roared with laughter after every scene with Eugene Levy and John Candy, and the warmth they felt with this young movie star in the making named Tom Hanks. Ron Howard was just getting started with his directorial dominance he commanded in the 80s and 90s, and while there are several other of his films that you might know better, “Splash” is one of his best. It might get a little bit heavy on the romantic cheese, but the hilarious scenes with the surrounding cast members more than makes up for it.
Best line: “I’m a really nice guy — if I had any friends they’d tell you.”
77. The Life Aquatic With Steve Zissou (2004) Directed by Wes Anderson
Let it be known that I think Wes Anderson is a massively overrated director. His films are over-produced, overwrought, overcast, overthought, over-fussed over, and for the most part, here in 2023, I’m over him. But there are a few diamonds in the rough when considering his body of work, and “Steve Zissou” is one of those exceptions. Bill Murray delivers a solid (and maybe a touch too precious) performance, but it’s the surrounding cast that deliver the magic. Anderson movies are always stuffed to the brim with big names which generally bogs down his films with too much personality, but the presence of Willem Dafoe, Jeff Goldblum, and Kate Blanchett only serve to spice up the film in a healthy way. Owen Wilson manages to give a rare performance that isn’t terrible, and while the movie gets close to over-doing it in typical Anderson fashion, it pulls back on the generic comedic tropes of his other films and stands as a pretty damn funny experience. And those of us raised in the 70s will find plenty to be nostalgic about with all of the Jacques Costeau references.
Best line: “I’m not going to fail you, but you all get in-completes.”
76. O Brother, Where Art Thou? (2000) Directed by The Coen Brothers
Moving down the inclusions of Coen Brothers movies that will be present on this list, “O Brother” is one that took a while to grow on me. When I saw this in the theater, it didn’t strike me as all that funny. I think I was expecting something a little more intense given their previous two films, and while I enjoyed the general feel of the adventure, the experience felt a little flat. Well, time has certainly rectified the way I feel about this little gem of a picture. In essence, “O Brother” seems to be an exercise in using the people they love to create caricatures to laugh at while tying it into one of the most widely known works of literature in existence. George Clooney, John Turturro, and Tim Blake Nelson look like they’re having a blast looking stupid, and the Coens can’t wait to put them in situations that are way over their heads. Lots of people love the way the music is tied into such a classic tale, but it’s the performances of the three leads that steer this film into the promise land.
Best line: “Alright…I’m with you fellas.”
75. The Bad New Bears (1976) Directed by Michael Ritchie
What makes “Bad News Bears” such a glorious film lies in its testament to the times. Back in the 70s, there was a minuscule window in history where kids could run around smoking, drinking, cussing, and using racial epithets, all in a PG-rated movie — ya know, kids talking like kids really talk. Not that these things alone make a good movie, but “Bad News Bears” acutely understands that there is a way of diffusing this language with humor and levity. The snowflake brigade of 2023 would have a field day canceling this movie in modern times, but luckily this little gem of a film came out long before those shitheads could have an opinion on it. What’s even better more evolutionary about this movie is the mature way children are looked upon, and how damn funny they are. This film is generally one of my all-time favorites, and as a comedy I think it’s where it belongs. It’s a great comedy, sports film, drama, and social commentary, so it’s challenging to try and sum up all of the parts that make this film such a unique watch. There’s nothing quite like it, and the funny moments stick with you for reasons that expand beyond a typical comedy.
Best line: “Yeah, it took several hundred years.”
74. Bruno (2009) Directed by Larry Charles
Sacha Baron Cohen has the largest balls in the history of anyone having balls. This dude has my lifelong respect for going to the ends of comedic earth to get a laugh, and you should give him the same respect too. No one in history has better exposed the disconnect between those smart enough to understand a level of humor, and the morons who automatically get offended by a brand of comedy that’s far too smart for them to ever grasp. In Bruno, Cohen sacrifices his well-being to point out idiotic American culture, and illuminates how frighteningly dumb the general population is happy to be. Call it offensive, call it unnecessary, call it shocking — I call it brilliant.
Best line: “Do you think house music could have ended WWII?”
73. Roxanne (1987) Directed by Fred Schepisi
Any film with Steve Martin needs to immediately be considered as one of the best comedies of all time. If any comedy was the sole vehicle of its titular star to show off their immense talents successfully, “Roxanne” is one of the best examples of it. The supporting cast does a good job of just getting out of Martin’s way so he can absolutely own every frame of this film, and it’s all the better for it. We all know the origins of the basic story here, and Martin isn’t as interested in re-creating it as he is with doing the things he does best: wordplay and physical comedy. “Roxanne” could easily fall apart with sentimental sloppiness, but Martin steers the ship with an intelligent edge that presupposes a certain level of savvy from the audience. This type of comedy is a dead art form now, so watching “Roxanne” only gets more satisfying as time goes on.
Best line: “It’s fish bait, right?”
72. Ferris Bueller’s Day Off (1986) Directed by John Hughes
Is it weird that I always rooted for Edward Rooney? When I saw this back in the 80s, just entering into high school myself, I couldn’t understand any sympathy given to Ferris Bueller. This little asshole skipped school, pressured his friends, lied to his parents, and was celebrated for it. When his sister, played by Jennifer Grey, says to Charlie Sheen, “why should he get away with it?”, I remember agreeing wholeheartedly with her, and I openly dismissed Sheen’s response of, “spend less time worrying about your brother and more time worrying about yourself”. I still kinda dismiss that logic within the context of the movie, and the beauty of this film is rooted with all of the friction Ferris gets, namely from Jeffrey Jones and Alan Ruck. Look, I understand why this film was such a hit with the slackers and generic partiers that rejected any idea of parental supervision being a positive thing, but as a straight-arrow student who never missed class and enjoyed getting good grades while my elders guided me along, I openly celebrate what Principal Rooney is trying to accomplish here. Jones steals the movie, and it’s only as I get older that I appreciate the equal time Hughes gives to his antagonist. You’re free to choose sides in art, and if you view this film as Ferris being the little shit that he is, there’s a lot of entertainment to be found.
Best line: “Why don’t you just come on down here and smooch my big ‘ol white butt.”
71. Stir Crazy (1980) Directed by Sidney Poitier
Richard Pryor and Gene Wilder made an amazingly funny duo against the odds, and while their work together was hit and miss, “Stir Crazy” showcases the rare energy these two had. Sidney Poitier seems to have an understanding of the magic bustling between his two stars, and there’s a genuine feeling of improvisation occurring between Pryor and Wilder that cannot be expressed on the written page. Poitier is smart enough to just lean back and let it happen, while sprinkling in some hilarious supporting performances in good measure. As a goofy comedy, there’s very little that doesn’t work with “Stir Crazy”, and some of the prison scenes actually garner some heartfelt emotion creating palpable sympathy for characters that, in the hands of a lesser director, would seem shallow and superfluous. More than anything, though, you get a warm feeling that all of the people involved with this movie had a blast making it. This is a spectacular comedy that has only gotten better with age.
Best line: “He’ll snort on ya, fart on ya…do anything he can to prance on your head.”
70. Happy Gilmore (1996) Directed by Dennis Dugan
This is one of a few guilty pleasures on this list as I generally cannot stand Adam Sandler movies, but every once in a while he actually comes through and shows us something different. Sandler does his comedy schtick for the most part, but the movie’s true charm comes from those around him. Carl Weathers as Chubbs is a particular highlight, but let’s not forget the great Christopher McDonald as Shooter McGavin and Bob Barker showing up to kick the piss out of Gilmore on the green. This movie shouldn’t work when you think of its premise, but from top to bottom it’s a laugh out loud goof-fest with all of the players on top of their game. Even Ben Stiller shows up as an evil old folks home tenant who’s only content when he’s torturing old timers too ancient to fight back. Sandler comedies generally fail miserably, but “Happy Gilmore” stands the test of time.
Best line: “Where were ya on that one, dipshit?”
69. Risky Business (1983) Directed by Paul Brickman
File this under the list of films I saw at too young of an age. The fact I was watching this in the theater at age 11 didn’t change the way I loved what I was seeing. “Risky Business” is one of those films that changed the industry for a couple of reasons, one of the more obvious ones being it was the first time Tom Cruise was the main star of a film. The other reason being it encapsulated a Reagan-era birthright of young Americans being obsessed with personal wealth and power. It also featured an extremely hot Rebecca DeMornay getting naked which is an entirely different story — watching “Risky Business” was one of those moments as a young boy where my sexuality became rock solidified, if you catch my drift. Notwithstanding, what makes any comedy great can only be summed up by the aggregate parts, and this is no more so than with the supporting cast of “Risky Business”, namely Curtis Armstrong. He owns every scene he’s in, somehow outshining the force that is Cruise, and leaves us begging for more of that Miles wisdom. This is a comedy that changed the landscape, and with stellar acting and a great soundtrack, its themes still ring true today.
Best line: “I think you jumped on your bike, peddled home, and whacked off.”
68. Heathers (1989) Directed by Michael Lehmann
If you were in high school when “Heathers” came out, this movie was your pièce de résistance; your visual savior; the way and the light; the most quotable film ever. It’s hard to underscore the massive impact this film made of a certain age group at the time, and what’s even more fun is the pointed messages it still can make today. As a precursor to today’s culture, where everyone is self-obsessed beyond all recognition, “Heathers” acts as a filmic Nostradamus. And man, is it funny. There’s not a single wasted second here, and the casting couldn’t have been more perfect. To try and describe the film would be a disservice, but at the end of the day, its message is clear: humans suck. But that doesn’t mean we can’t laugh at that truth. There are so many classic lines in this film it would be next to impossible to choose a favorite, but here’s my best effort:
Best line: “Some tribe of withered old bitches doesn’t want us to terminate that fleabag motel, all because Glen Miller and his band once took a shit there.”
67. The Cable Guy (1996) Directed Ben Stiller
Does anyone remember how panned this movie was when it came out? And do you also remember how wrong those people were? I was utterly dumbfounded with the way this beautiful movie was received when it was released, and I can only attribute it to one thing: it’s way too smart for its own good. A smart comedy can be the kiss of death when it comes to American audiences who want to see obvious jokes, music queues, and moments that tell them when it’s ok to laugh. “The Cable Guy” isn’t interested in holding anyone’s hand, and that’s where it shines. This film is another example (you’re probably noticing a theme here) of where the filmmaker wants to expose society for being the dumbed-down sheep herd it happily is. And Jim Carrey in arguably his best role ever doesn’t hurt things either. Carrey gleefully goes well over the top, mainly in a very sinister way, thus confusing the shit out of mainstream audiences. Those of us who like our comedy challenging, though, are treated with ample doses of hilarity, intensity, and straight up awkwardness as the tale of growing up in a televised nightmare unfolds.
Best line: “No ifs, ands, or buts….well maybe a few butts.”
66. Meet The Parents (2000) Directed by Jay Roach
I didn’t want to like this movie. It seemed destined for failure and unfunny boredom. And in some ways it is — the movie begins tepidly with some overly emotional romantic garbage, and it quickly gives off the air of suckage right off the bat. But it quickly rights itself the moment Robert De Niro comes on screen. His turn in comedy here, with his evil-planner-petting-his-kitty vibe, keeps this movie afloat where it wouldn’t have survived with any other actor in his place. Ben Stiller seems genuinely afraid of him which only cements a very funny chemistry between the two. “Meet The Parents” isn’t perfect by any means, but De Niro is so brilliant you don’t mind looking the other way.
Best line: “Are you a pothead, Focker?”
65. Bad Santa (2003) Directed by Terry Zwigoff
This is one of those instances where I’m happy to judge a person’s character dependent on how they react to “Bad Santa”. It’s like if someone tells you their favorite band is Phish, or someone explaining the virtues of being a Jehovah’s Witness — you just know that person’s decision-making process is seriously flawed. Terry Zwigoff proves he’s the only one who could have given this film such a flair, and he recently told the now sadly departed Gilbert Gottfried that he wanted the film to be even darker. It matters not, though, as the participants give all of themselves to the dark and shitty vision of Christmas consumerism in all of its ugly reality. As with any great comedy, it’s the surrounding players that make “Bad Santa” what it is, particularly John Ritter and Bernie Mac, but it’s Zwigoff’s direction that turns this film into something truly hilarious.
Best line: “More booze. More bullshit. More buttfucking.”
64. Beetlejuice (1988) Directed by Tim Burton
I generally believe Tim Burton has only made three great movies in his lifetime, and they all happened by 1994. Beetlejuice would be his second best (you can keep scrolling down for his best). “Beetlejuice” is flat out one of the most original movies ever made, and there’s nothing anyone can ever say to refute that. Mainly, though, it’s a vehicle to show what a super talent Michael Keaton is. He cut his chops in comedy, and the guy knows what he’s doing when it comes to making people laugh. Burton does a beautiful job creating this bizarre world around him, and Keaton’s presence in the movie is relatively sparing, but when he is on the screen he dominates. As always, Jeffrey Jones proves that he can act in whatever role you have, and he finds a way to steal whatever scene he’s in. Burton spins this tale in such an eccentric world the viewer is very easily distracted to any glaring plot holes that exist, making the suspension of disbelief a very natural enterprise. As fun as “Beetlejuice” is to look at, though, it’s Keaton’s performance that is its driving force.
Best line: “I’ve seen the Exorcist 167 times, and it keeps getting funnier every time I see it!”
63. Better Off Dead (1985) Directed by Savage Steve Holland
As you have already noticed by now, I’m a massive fan of 80s comedies that were subversive enough to push the boundaries of a PG rating and at the same time have no chance in living hell of being made at all in the 21st century. “Better Off Dead” is part of that group, existing as a goofy call to arms to those of us who were kids when this classic comedy dropped into theaters. It’s one of those movies that contemporary reviewers claim has enjoyed a recent renaissance, but the truth is “Better Off Dead” was highly revered from the moment it released. The reviewers and critics of the day panned it, but the rest of us knew the truth. It’s kind of a spiritual relative to what John Hughes was doing with comedies like “Weird Science”, but the dedication to existing in its own world and hammering home truly inspired laughs have always made “Better Off Dead” a wonderful oddity of politically incorrect comedy that’s become all but extinct now. To this day, it’s the best thing John Cusack has ever done, and the great Curtis Armstrong manages to steal the show, as he did with pretty much every comedy he was ever in during his heyday in the 80s.
Best line: “Do you have any idea what the street value of this mountain is??“
62. A Mighty Wind (2003) Directed by Christopher Guest
What is there to say about the Guest movies that hasn’t been said? “A Mighty Wind” expertly lets people shine when they need to shine, and the immensely talented cast is humble enough to step back and give the limelight to wherever the laugh is. But this film belongs to Eugene Levy, hook, line and sinker. As much as you’re laughing at these bands of goofballs masquerading along with their intense levels of devotion to a genre of music that has enough comedy embedded into its fabric as it is, Levy manages to pull some sympathy out of us with his brilliant performance.
Best line: “You know, 35 years ago, preparing for a concert meant playing ‘find the cobra’ with the hotel chambermaid.”
61. Tootsie (1982) Directed by Sydney Pollack
“Tootsie” is a movie full of flaws. There’s obnoxious 80s music and goofy montages, the writing is mostly flabby and dumb, the surrounding performances are a mixed bag, and Pollack’s direction is generic and average. But then there’s Dustin Hoffman. If you ever want to see how a singular performance can otherwise transform a bad movie above the sum of its parts, I urge you to watch “Tootsie”. Hoffman leaves zero doubt as to why he is one of the 10 greatest actors in the history of film with this performance, delivering half-assed lines with so much gusto and spice that you forget the fact the movie itself is a piece of shit. The point of the movie on paper is the yawn-inducing idea that women need a pretentious man to point out inequities between the sexes, and the twist is that the man gets found out and the woman storms off in a huff. Then in the end, she falls in love with him anyway and they stroll off happily ever after. Are you asleep yet? Even with this dopey premise, though, Hoffman destroys so hard with Dorothy Michaels that you’re too entranced to care. And that’s the magic of film in a nutshell. Shout out to Dabney Coleman for being the best supporting device in the movie.
Best line: “I begged you to get some therapy.”
60. Tommy Boy (1995) Directed by Peter Segal
I suppose this is another guilty pleasure of mine, but sometimes a film is so dedicated to its goofery that it ends up being close to perfect in its execution. It’s also the only instance where Chris Farley got to show off his genius in film form. David Spade is ok as the sidekick, and Dan Aykroyd briefly pops as the antagonist, but it’s Rob Lowe and Brian Dennehy that provide the best comedic support. If you’re ok with just going with the flow and allowing the whirlwind talent of Farley to take you to other places, the insipid storyline won’t bother you at all.
Best line: “He’s a big dumb animal, isn’t he, folks?”
59. Shaun Of The Dead (2004) Directed by Edgar Wright
As a fierce protector of legacies I love, I was very defensive of the idea a comedy would be made based on one of the greatest films of all time, “Dawn Of The Dead”. Why go there? Just leave George Romero alone, I thought. As I watched the film for the first time, it slowly “dawn”ed on me that these British fellas were making one of the greatest homages to film the world has even seen. Romero was so impressed himself that he invited these guys to be in “Land Of The Dead” a year later, forever supplanting that they live on forever within the Romero ecosphere. As comedies go, “Shaun Of The Dead” is about as original as they come. With enough gore and legitimately scary moments it manages to be a better horror movie than 95% of the garbage out there, but its motivations are absolutely steeped in the world of laughs. It’s also a buddy movie and a romcom and an action adventure, blah blah blah, but you’re always laughing regardless of where the movie steers you. And the record-tossing scene alone is enough to satisfy any record-collecting Gen-Xer out there.
Best line: “Sup, niggas!”
58. Willy Wonka and The Chocolate Factory (1971) Directed by Mel Stuart
Back when children’s movies actually had a message. Back when people weren’t talked down to. Back when kid’s movies had some semblance of menace to them to prove a bigger point. Back when scaring the shit out of a kid was a necessary tool in order to attain a larger wisdom. Seems alien in these times of moronic superhero drivel, money obsession, and placated egos, right? As a child of the 70s, I was completely changed by seeing this movie, and time has shown I’m not the only one. It’s arguably the greatest children’s film ever made, and features one of the greatest performances ever with Gene Wilder. His droll and sarcastic lines to the scheming little asshole children are delivered with perfection, and Wonka’s reactions to the adults in light of their inability to parent has a huge beaming strobe light shining into their clueless eyes. Ultimately, this story is about a society losing itself, and the importance of getting it back with the correct education. Being a smarmy pedagog in order to achieve that is right up Wilder’s alley. This movie would be higher on my all-time favorite general list, but as a comedy, it’s where it belongs.
Best line: “There’s gonna be a lot of garbage today.”
57. Kingpin (1996) Directed by The Farrelly Brothers
Words can hardly express how happy this movie makes me. It’s full-on Tomfoolery, and who doesn’t enjoy succumbing to that? It suffers from that Farrelly brother montage syndrome, and gets pre-occupied with teaching the audience lessons, but when it takes a step back and lets Bill Murray and Woody Harrelson be funny is when it fires on all cylinders. Randy Quaid steps up his game in a big way with a hilarious performance of his own, blending into the vibe perfectly. This is one of those movies where once you let yourself go in the absurdity, you’ll be richly rewarded. It’s also arguably Bill Murray’s funniest role ever, which is saying a hell of a lot.
Best line: “Hi. Not you. Hi.”
56. Ace Ventura: Pet Detective (1994) Directed by Tom Shadyac
In my opinion, this is the greatest Jim Carrey performance ever. Forget his dramatic performances, forget Eternal Sunshine, forget Mask, forget In Living Color, forget all that crap…Ace Ventura is Jim Carrey is at his unbridled best. Whenever you need to just feel good about life and laugh your ass off, this is an excellent go-to option. Carrey moves through this picture showing that he is indeed the Jerry Lewis of modern times, and then even more. It doesn’t really matter how silly the film is as Carrey displays a true talent the world has never seen — his timing, his physicality, and his acting ability all work in concert to present a truly inspired performance. Hell, this movie is so silly that even Tone Loc and Dan Marino being present doesn’t hinder things, and we also get to see Sean Young in her panties. What more could you ask for? Just don’t spin her around or you will indeed get more than you asked for.
Best line: “She is suffering from the worst case of hemorrhoids I have ever seen!”
55. After Hours (1985) Directed by Martin Scorsese
Perhaps Martin Scorsese’s most underrated movie, including “After Hours” here in the comedy list seems a bit tricky. Indeed it is very funny, but the film is many others things as well. It’s very dark, bleak, and dreamlike, and it no doubt challenged audiences when it was released upon audiences over 30 years ago. The premise is pretty simple: normal dude gets thrown into a situation that’s way over his head, and he spends the night trying to work his way out of a suffocating predicament. But in the hands of a master like Scorsese, that simple storyline is only a backdrop to the complexities of everything you’re actually seeing on screen. The editing, the direction, the acting and the laughs are in fighting form, leaving us breathless and chuckling in wonder at what we just witnessed. Dunne is excellently cast in this role giving it enough charm and humor to propel all of the excellent supporting players around him. More than anything, though, this film will speak to any male of the species who’s ever been courageous enough to date different women as a responsible adult, which is a state of trench warfare in itself.
Best line: “Pal, I’ve been asking myself that all night.”
54. Fear And Loathing In Las Vegas (1998) Directed by Terry Gilliam
Few movies have the ability to be laugh out loud hilarious and stone cold frightening at the same time, but Terry Gilliam pulls it off with “Fear And Loathing In Las Vegas”. Gilliam lost his way as a filmmaker after this one, but the films he produced up to this point were all so brilliant in their own way that we can give him a pass. When it comes to visualizing Hunter S. Thompson’s hallucinogenic visions, films have really never properly transformed his written words into anything that’s remotely watchable. Johnny Depp and Benicio Del Toro give their greatest performances trying to make sure that the trend discontinues here, and Gilliam clearly gives them the proper motivation to make an exceedingly entertaining and disturbing comment on society. It’s always been interesting that Gilliam, who’s never been a drug user, can come along and provide the proper cinematic context to the words Thompson created whilst being high on every drug ever created, and at the same time. It only proves that you don’t have to be in a different dimension to see the crumbling around you, and whether you’re high or sober, there’s always room to laugh at the ugliness.
Best line: “..and his pants are constantly encrusted with semen from jacking off when he can’t find a rape victim.”
53. The Burbs (1989) Directed by Joe Dante
This might be me being an unapologetic child of the 80s, but I don’t care: “The Burbs” is one of the best comedies out there. I wouldn’t argue it’s the greatest Joe Dante film, but it’s certainly the funniest, and it plays to anyone with a dark and sardonic sense of humor. Dante exhibits all of his love for cartoon goofiness, and wraps it up in a sinister tone — ya know, like the classic cartoons were so great at accomplishing. “The Burbs” is one of those films where you’re a little surprised it ever got made, but with Tom Hanks on board one would have to imagine that his involvement bankrolled the idea. Not that Hanks is a bad inclusion by any measure — the guy knows how to make us laugh, and “The Burbs” came out at a fertile time when he was first becoming a megastar. The supporting cast does a great job selling the horror of the plot, but no matter how weird it all gets, we’re still laughing all the way through it.
Best line: “Hey! Pinocchio! Where are you goin’?”
52. Wild At Heart (1989) Directed by David Lynch
As you can probably tell, I appreciate my comedy mixed with horror, and there might not be any better example than “Wild At Heart”. This movie makes you want to laugh and puke with equal measure, and it’s all the more exciting because of it. I wouldn’t say I’m a massive Lynch fan, but “Wild At Heart” is the director at his unapologetic best, pushing boundaries and blurring the line between what an audience can handle. Should we be laughing at characters as awful as Bobby Peru? Too late, you just did. Now you really gotta think this through, right? Lynch obviously loves challenging his audiences this way, and while most of his movies never quite get that balance right, “Wild At Heart” succeeds on every possible level of comedy, horror, drama, and whatever else pops up into the brew. Nicolas Cage and Willem Dafoe are the reasons to watch this film as they, like Lynch, relish in the time they get to freak out audiences. This film is truly a laugh out loud experience, all while holding back your gag reflex.
Best line: “Not right now, honey, I gotta take a piss!”
51. My Cousin Vinny (1992) Directed by Jonathan Lynn
“My Cousin Vinny” is yet another film that just shouldn’t work at all, but thanks to the cast knocking it out of the park, they turn a run-of-the-mill feel good comedy into an inspiring and hilarious piece of work. Somehow Joe Pesci and Marisa Tomei have an awesome chemistry together, provoking each other into performances that get better and better as the film progresses. There isn’t a single moment in this film where you’re not engaged, and the courtroom drama is actually well-staged and delivered. Tomei earned a well-deserved Oscar for her performance as she is just as much a main player as Pesci is. “My Cousin Vinny” is another classic example of a movie turning into something much bigger thanks to the actors on screen.
Best line: “Oh, there’s a fuckin’ surprise.”
50. Time Bandits (1981) Directed by Terry Gilliam
No boy in the history of boys can say a single negative thing about “Time Bandits”. I dare you to try. Say the words “Time Bandits” to any male between the ages of 30 and 60 and watch the massive goofy smiles spread across their faces. To this day I get lost in wonder with this gorgeously-realized nightmarish playground that only Terry Gilliam could deliver. What the director does best here revolves around treating the boy as the most mature one of the bunch. He’s the only thoughtful individual, lost amongst materialistic and shallow adult monsters. The midgets aren’t cute and cuddly little love-muffins, they are scheming, greedy little bastards, and it’s up to the child to keep things in any semblance of order. As a child, there’s no better message once can receive in a film, and Gilliam understands this angle beautifully. It’s the parents this film talks down to, and “Time Bandits” respects the intelligent child wholeheartedly. But this never comes across in a hokey way — Kevin is clearly annoyed with the adults creating a world where hope is an unattainable precept. Even The Supreme Being is bored with his creation — when Kevin asks him why we need evil, he lazily responds, “I think it has something to do with free will.” In the pantheon of great comedies that can easily exist in other genres, “Time Bandits” stands proudly as one of the best of all time.
Best line: “Slugs! HE created slugs! They can’t hear. They can’t speak. They can’t operate machinery. Are we not in the hands of a lunatic?”
49. The Princess Bride (1987) Directed by Rob Reiner
Is it even necessary to explain why this movie is great? How often do you get to stuff a movie full of stars and still have it pierce through the collective world consciousness without making it seem as if the movie was a vehicle for actors to be self-obsessed prima donnas? The real star of “Princess Bride” is Rob Reiner, making sure that the story is told perfectly, and insuring the cast just lay back and let the magic on the page happen. There’s not a single bad moment in this film, and I don’t need to explain to anyone why this is. Just go watch it again, you know you want to.
Best line: “Rest well, and dream of large women.”
48. Dirty Rotten Scoundrels (1988) Directed by Frank Oz
This may come as a surprise for people who weren’t around in 1988, but “Dirty Rotten Scoundrels” was not well-received in its day. People noted that it was offensive and degrading to women, and well beneath the cast and crew making it. Apparently they didn’t stick around for the ending. Over the years, this little gem has garnered more and more respect, and with all of the moving parts working so well in harmony it certainly deserves to be celebrated down through the ages. Frank Oz has a real knack for dark comedy, and what makes “Scoundrels” work so well is we really do dislike every single character we see. There’s literally no redemptive qualities to any of the main players, and herein lies its charm. If a filmmaker is busily winking at the audience making it clear they don’t really feel this cynical, then the message gets messily lost. Oz doubles down and makes sure there is absolutely no wriggle room for viewers to feel even a smidge of sympathy for the shitheads on screen. It’s a beautiful maneuver, and you can see the sheer joy of playing these people on the faces of Steve Martin and Michael Caine, who give us some of their greatest performances. Glenne Headly does an awesome job as the hidden scoundrel, and by the end of the film, you can’t believe you love these professional scumbags so much.
Best line: “To be with another woman, that is French. To get caught; that is American.”
47. Rushmore (1998) Directed by Wes Anderson
My only other entry on this list from Wes Anderson is “Rushmore”, and it’s hard to describe the impact this film had on the world when it came out back in 1998. It was original, hilarious, sad, odd, and didn’t really exist in the real world, just like most of Wes Anderson’s films. What makes “Rushmore” a step above any of Anderson’s other films, however, is the newness of his style at the time, and the fact it was cast carefully rather than arbitrarily. What I mean is this: Anderson’s films after “Rushmore” only seem to be vehicles to cram as many huge stars as possible into a two hour timeframe. I know people love Anderson films, but I’m not one of them. A talent like Wes Anderson can only be discovered once, and therein lies the beauty of “Rushmore”, with its lavish art direction and subtle performances. Bill Murray is at the very tip top of his game, and Jason Schartzmann arguably delivers his only watchable acting job. “Rushmore” built Wes Anderson’s entire career, landing out of nowhere and changing the entire landscape.
Best line: “Yeah, I was in the shit.”
46. Evil Dead 2 (1987) Directed by Sam Raimi
My list of movies that I think are funny don’t need to be considered “comedies”in the classic sense — they need only make me laugh. The single most glorious homage to the Three Stooges in history is “Evil Dead 2” without a shadow of a doubt. Sure, it’s dressed up like a horror movie, and does actually have a few scenes of freakiness and general weirdness, but there’s not a single moment in its 90 minute running time where you’re not busting a nut giggling hysterically. The term “cult status” was created for movies like this, with its winks to underground horror and comedy alike, and Bruce Campbell’s Ash is one of the dopiest and most awe-inspiring goof-festival of acting you’re ever likely to see. Campbell has absolutely zero fear or shame, and with Raimi’s relentless directing style we get one of the great comedies of our time.
Best line: “Who’s laughing now??”
45. Anchorman (2004) Directed by Adam McKay
In terms of sheer goofery at its highest possible level, “Anchorman” stands proud and true as one of the most purely inventive of all time. Most absurdist comedies always seem to go on too long whatever their respective running times are, but “Anchorman” figures out a way to not waste a single second and end on the perfect note. Will Ferrell is the funniest he’s ever been, and his surrounding cast is absolutely stellar. Every scene in the movie is filled with memorable one-liners and laugh out loud moments while never once feeling forced. You can tell this movie was blast to make for all of the cameo appearances that flood the screen, but the movie shines brightest when its four stars — Ferrell, Paul Rudd, David Koechner, and Steve Carrell — bounce off of each other. The sequel to this film was a glistening turd of opportunism which dulls the flame of this original somewhat, but even that dud of a movie can’t kill off the magic of “Anchorman”.
Best line: “Let’s dance, dickweed.”
44. Monty Python and The Meaning Of Life (1983) Directed by Terry Jones and Terry Gilliam
You’ll be seeing much more Monty Python on this list, but “The Meaning Of Life” has gotten somewhat of a bad rap over the years. Python purists argue that this movie was a step back to the one story brilliance of their previous films, stumbling backwards into sketch-style comedy that should be left off the big screen and reserved for television sets only. While a sound argument can be made that the theme of this film is as loose and ambiguous as our galactic presence itself, it doesn’t cloud the fact that this film has some of the funniest Python bits of all time. Mr. Creosote, liver donors, and sex education are among some of the most hilarious comedic strokes ever to land in a film, and Eric Idle’s songs hit a hilarious new peak. “Meaning Of Life” might be a hark back to their television sketches, but how on earth is that a bad thing?
Best line: “Better get a bucket, I’m gonna throw up.”
43. Return Of The Living Dead (1985) Directed by Dan O’Bannon
It’s really kind of amazing how well “Return Of The Living Dead” works. Its basis is in horror, but this is a comedy through and through. It also needs to be mentioned that horror movies simply were never this funny prior to “Return” being released. Where “Dawn Of The Dead” had more subtle humor poking fun at consumerism, and “Evil Dead” was a clear homage to the Three Stooges, “Return” made the decision to let the humor lie in the acting of the performers. This required a deft touch, where Dan O’Bannon enters into the picture. O’Bannon was no stranger to comedy and horror, having written classics like Dark Star and Alien, and the director makes no qualms about his everlasting love of Romero-style zombie action with his characters directly talking about the films themselves. In some subversive ways, this was a pre-Tarantino approach to making films, openly acknowledging his love of other film makers so he could then spin his own tale of disgust and world-ending action. O’Bannon proves why he was such a special writer when you listen to the dialog in “Return”, and in lesser hands this movie could have been a real disaster. The end result is a hilarious romp through all of the horrific amusement we get from being scared.
Best line: “It’s not a bad question, Burt.”
42. Ed Wood (1994) Directed by Tim Burton
There aren’t many movies out there more endearing than “Ed Wood”. A love letter to the worst film maker of all time (if you don’t count Jordan Peele), this is a rare instance where Burton is able to assemble a star-studded cast and not completely burn the end product to the ground. Johnny Depp is fantastic in the title role, and the supporting cast of Sarah Jessica Parker, Bill Murray, and Jeffrey Jones are absolutely perfect. But “Ed Wood” belongs to Martin Landau from start to finish. Every second he’s on screen is a brutally honest and hilarious testament to a complicated and tortured human being trying to prop himself when he knows he’s on his last legs. It’s a story of friendship with gut-busting pizazz.
Best line: “Karloff does not deserve to smell my shit!”
41. Tropic Thunder (2008) Directed by Ben Stiller
In a lot of ways, “Tropic Thunder” is the last bastion of politically-incorrect comedy. This film couldn’t be made today, just 15 years after its release. Cancel culture would been so busy crying itself to sleep after watching this film that it never would have left the editing room, but thankfully it came out when it did and was filled with enough star power that nothing could have squashed its momentum (Here’s a secret, white woke warriors: black people love this movie). “Tropic Thunder” is about as scathing an indictment of Hollywood as you’re ever likely to see with some of the best comedic performances in the history of cinema to boot. Namely it’s Robert Downey Jr. and Tom Cruise that throw this movie over the top with their eye-watering performances, but there’s nary a misstep with any decision when experiencing this comedy classic. The full retard scene itself can easily be placed in the pantheon of brilliant writing and filmic execution, while the size of Cruise’s hands is enough to send this writer into hysterics without the actor saying a single word. Many films that have these types of all-star casts flounder into boring idiocy, but Stiller pulls off one of the great tricks of all time, managing all of the mega-talent without lessening his vision. “Tropic Thunder” easily encapsulates what makes high-brow humor so childishly hilarious. Side note: listen to the commentary on the blu-ray where Downey Jr. commentates in character — it’s funnier than the goddamn movie!
Best line: “You was fartin’ in bath tubs and laughin’ yo ass off…”
40. Night Shift (1982) Directed by Ron Howard
It’s always fun to point out a movie I find to be massively underrated, and there might not be a comedy more deserving than “Night Shift”. The direction, acting, and writing all come together to make one of the most uniquely satisfying comedies to ever come down the trail. The movie is essentially about love and friendship, but Henry Winkler and Michael Keaton concoct a chemistry unlike any we’ve seen before. “Night Shift” manages to be heartwarming without being hokey, and hilarious without any cheese. The undertone of prostitution in NYC gives the film a fresh edge, and Winkler and Keaton ramp up their talents to keep every scene fresh and funny. “Night Shift” is absolutely a film that deserves new attention.
Best line: “You’re gonna play tennis…with GOD.”
39. Hollywood Shuffle (1987) Directed by Robert Townsend
Speaking of movies that need to find new audiences, “Hollywood Shuffle” might be at the top of the list. When I saw this in the theater at the tender age of 15, I can remember the audience going ape shit with laughter, and that’s the best way to experience comedy. It really nailed a certain time in history, and the mixed-race audience I saw it with shared a great moment in time together. Those of us who paid attention to stand up comedy in the 80s definitely know the name Robert Townsend, and this film was his attempt to lampoon Hollywood’s inherent racism, and the resulting difficulties for black actors to keep their pride while slogging amongst it. The result is simply one of the greatest satires of all time. Townsend fills the screen with skits that never fail, and he’s not afraid to embrace the slang and political-incorrectness of the time. It’s hard to choose a favorite bit from this great flick, but Sam Ace and Attack Of The Street Pimps are hard to beat. There’s a huge heart pumping through this movie, but it’s never so distracting that it quells your laughs. An absolute classic that you’ll be quoting the rest of your life.
Best line: “Was it one of my dames? Nah, it was just a fag.”
38. Sideways (2004) Directed by Alexander Payne
I Payned (see what I did there?) in including this film in the comedy list as “Sideways” is so many things at once, but at the end of the day, I have to include the films that make me laugh over and over again, and this film is one that never fails to make me smile. I must admit that I didn’t get this movie when I saw it for the first time. I thought Thomas Haden Church’s Jack was a total and complete scumbag, and I didn’t give a shit whether he found happiness or not. But then I grew up a little and had a few more adult experiences. What I love most about Sideways, and what kept it out of my mental reach for so long, is its focus on what makes people better in the face of those around us pissing us off. It’s about allowing our friends and family to fuck up, and still opening ourselves up to continue loving them. It’s about accepting that we’re no better than anyone else, and we’ll need all of the people we can in our corner for the times we fuck up ourselves. Mostly, though, it’s about laughing at all these human foibles and what makes us human. “Sideways” is a really beautiful film that has grown on me tremendously, and it never fails in making me feel better about people and their inevitable shortcomings.
Best line: “Don’t ask that up in wine country, they’ll think you’re some kind of dumbshit.”
37. Back To School (1986) Directed by Alan Metter
Words cannot express how affectionate I feel about “Back To School”, but I’ll still try. As a firm lover of Rodney Dangerfield and stand up comedy, this movie is the only time he was able to transfer his talents to the big screen and not have it end in a total flop. Dangerfield was almost too big a personality to accurately exist in a film, but thanks to the writing and story, the elements came together to create a non-stop package of hilarity from start to finish. It’s something short of a miracle that “Back To School” was able to exist as a PG-13 movie and still work, but this is testament to Dangerfield showing off his immense talent without having to go blue — something he was known and loved for. Danny Elfman pumped out an early soundtrack for it which absolutely gave the film some special spice, and, sadly, it’s the only movie to feature the absurdly late and great Sam Kinison. Comedies rarely get any better than “Back To School”, and comedians never get funnier, wittier, or more smart than Dangerfield.
Best line: “Why don’t you call me sometime when you have no class?”
36. A Fish Called Wanda (1988) Directed by Charles Chrichton
One of the more original comedies you’ll ever experience, “A Fish Called Wanda” is every bit as smart and goofy as any Monty Python sketch you can shake a stick with the extra added bonus of fully-realized characters to respond to. While the supporting cast are all pretty serviceable, Kevin Kline is the real attraction here, while Jamie Lee Curtis is a bit out of her element and Michael Palin is hilarious per usual. However, this is a John Cleese vehicle through and through — you can see his passion for his own project here, with arguably his greatest performance of his career.
Best line: “Why’d they name her after a car?”
35. Hot Fuzz (2007) Directed by Edgar Wright
There are very few times where we have the pleasure of seeing a movie made by a director who is so obviously in love with not just the craft of film making, but the medium of movies in general. Edgar Wright is clearly a lover of all types of film, and “Hot Fuzz” comes off like the best movie Quentin Tarantino has never made. In a strange way, Wright borrows every little thing in “Hot Fuzz” from films before it to create an experience altogether new. “Hot Fuzz” is obviously a direct homage to the film “Point Break”, “Bad Boys”, and any other buddy cop movie you can think of, but what emerges from the pile of apparent police influences is a tale of dystopian horror all wrapped up in an action-packed comedy. And how often can you say that about a movie? Per usual, Paddy Considine steals the show which is just expected at this point in time.
Best line: “Now who’s being childish?”
34. Vacation (1983) Directed by Harold Ramis
As I was writing this entry I googled “this movie”Vacation film” as to find an image to insert into my prose here. The 2015 remake was all that popped up which is enough to make my eyes twitch with annoyance. Yeah yeah, I know I’m old now, but I don’t even need to see the remake to know it’s a tired piece of shit, paling into pointless putrescence in comparison to the original. “Vacation” is rare proof that even a National Lampoon’s film can be well-thought out and written with the acting and directing talent to buoy its legacy for the rest of time. There isn’t a single dull second throughout its running time, and the pacing and performances are inspired and focused. Any Chevy Chase fan would probably agree that this is his best movie, and there’s very little here to dispute that approach. This film has, of course, spawned several sequels, none of them coming even remotely close to this brilliant original from Harold Ramis. The scene where Chase loses it in the car is stuff of legend unto itself.
Best line: “You’ll be whistling zippity doo-da out of your assholes!”
33. Groundhog Day (1993) Directed by Harold Ramis
Ten years after Ramis gave us “Vacation”, he delivered “Groundhog Day”, widely considered in most circles to be amongst the greatest films of all time. And why not? There really isn’t a single thing wrong with this picture, from the writing, to the performances, to the direction, to the message. One thing the movie benefits from is watching Murray go from smarmy bastard to slightly less smarmy bastard as he collects and humbles himself in the face of forced existential dread. It’s a brilliant move on Ramis’ part to confront someone so self-absorbed with ideas of death and purpose, ideas that Murray is too preoccupied to give any realistic credence to. A movie would be boring to try and delve into the brain of a whining middle-aged man consumed with self-importance to explore with any depth the subject of mortality (see “I Heart Huckabees”). By using a narcissist hellbent on his own satisfaction, and too consumed with himself to bother considering his own existence, “Groundhog Day” becomes one of the funniest and most poignant comedies about the chaotic foibles of humanity we’ve ever seen.
Best line: “This is one time where television really fails to capture the true excitement of a large squirrel predicting the weather.”
32. Slap Shot (1978) Directed by George Roy Hill
I can’t think of a single time where “Slap Shot” didn’t make me howl with laughter, and I’ve seen this film 100 times in my life. I wrote about this film a few years back in my “best sports films” list, so I’ll try to not repeat myself, but what makes “Slap Shot” so damn funny is the creative ingenuity of the dialog. So often in comedies the lines come out as forced set ups to trivial and cliched punchlines to the point where you can see the joke coming from a mile away like a runaway freight train on fire. “Slap Shot” pays off with each character being carefully written and considered within the context of each finely tuned scene. As insensitive as many people like to accuse this movie of, it’s actually one of the more delicately-realized examinations of how men and women effect one another in an otherwise macho past time. It’s simply one of the smartest comedies ever made, and it doesn’t hurt that it’s still as hilarious as ever.
Best line: “You better get re-married again, or he’s gonna have someone’s cock in his mouth before you can say Jack Robinson.”
31. Three Amigos (1986) Directed by John Landis
“Three Amigos” is one of those films that I take a lot of pride in loving. When it was released in 1986, it was panned for the most part. Reviewers didn’t get it, and as a 14-year old who loved every second of it, this was an important lesson in how full of shit most people are. The majority of reviewers out there have their own agendas and simply have no ability to objectively rate a film, and of course, now that people have had over 30 years to reassess “Three Amigos”, people now recognize it as one of the greatest pieces of goofery to ever make its way to a screen. It might be important to note that comedies in the mid-80s found the most success in the form of a John Hughes vehicle, filled with 80s new wave hits and young faces to drool over. John Landis wasn’t too concerned with this logic, preferring to work with three of the funniest people to ever grace our planet. Steve Martin, Martin Short, and Chevy Chase have a blast prancing around in their pretentious suits, acting the part of prima donnas in a situation far over their heads. Oddly enough, though, it’s the surrounding players that have the most precious material to work with, particularly El Guapo and Jefe. Sadly, Sam Kinison had a sizable part from the movie removed, and his filmed scenes have apparently been lost. The mind boggles at how much better this film could have been with Kinison imposing his will upon it.
Best line: “Do you have anything besides Mexican food?”
30. Planes, Trains, and Automobiles (1987) Directed by John Hughes
I feel like I’m starting to crack the true heavyweights of comedy classics with “Planes..”, but perhaps I’m being too nostalgic having been raised in the 80s. It’s hard to overstate the importance of this film, though. In some senses, “Planes..” is nearly perfect in its execution as a comedy. there’s no fluff, the performances are stellar, and the direction is as focused as a comedy has ever been. There’s a magic at work here that didn’t exist then, and doesn’t exist now. If there’s any minor weakness it’s Hughes’ penchant for sentiment, but that’s really just a preference, and hey, it’s how the guy liked to tell his stories. Steve Martin and John Candy absolutely shine in their roles, feeding off each other and making space for the other to show their talents. All of the back up characters are awesome as well, particularly an early performance from Dylan Baker as Owen. The most important aspect of “Planes..” lies in its ability to still be hilarious after all of these years, never aging, only gaining more momentum as the years pile on. As a side note, I highly recommend picking up the 4K disc released in 2022 as it contains an hour of deleted scenes that are absolutely hilarious!
Best line: “Larry Bird doesn’t do as much ball handling in a whole night as you do in an hour.”
29. Team America: World Police (2004) Directed by Trey Parker
All I need to do is type out the words “Team America” and I start laughing. That’s how seriously fucking funny this movie is. I feel like everything Trey Parker and Matt Stone create is made especially for me — maybe it’s because they’re roughly the same age as me and understand the comedic sensibilities of my generation. They grew up on the same films and TV as I did, understanding that timing is everything, and nothing is sacred. These are important approaches to making movies, and Parker and Stone have been able to build a long career out of being consistently hilarious. Whatever the reason I love these guys so much, it doesn’t much matter once I start watching “Team America” because I’m too busy peeing my pants with laughter to focus on anything else. The sex scene alone is worth a full price of admission.
Best line: “…lick my butt, and suck on my balls!”
28. An American Werewolf In London (1981) Directed by John Landis
“American Werewolf In London” is a true master class in film making. It works on so many different levels that it’s nearly impossible to discuss in one paragraph. I don’t know that I’ve ever seen a film that can change gears so effortlessly and successfully, and if there is a movie out there somewhere (other than “Werewolf”) that coexists so flawlessly in both the comedy and horror worlds, please, let me know. There isn’t much point in trying to pry apart the different genre elements at work here, but make no mistake about it: this is one funny fucking movie. What makes it so amusing comes from the unique ability of Landis being the auteur and out-and-out film buff that he is. When you hear him speak about this film it’s clear this was the film he always wanted to make, and it’s hard to argue that “Werewolf” might be his greatest achievement. As a comedy it’s tricky territory, though, as it’s every bit as unsettling and fucked up as it is hilarious and heart-warming. And that’s the film’s saving grace in a nutshell; its ability to completely stand on its own, apart from any other movie you’ve ever seen. It’s an endlessly entertaining and horrific slice of hilarity that absolutely exists in its own rarified air.
Best line: “Life mocks me even in death!”
27. Young Frankenstein (1974) Directed by Mel Brooks
Number 27 is low for this movie in comparison to most other lists out there, and maybe I’m way off by putting it this far down. There’s no doubt that Gene Wilder is absolutely brilliant here; his presence seems to step up the game of everyone else around him. Mel Brooks was on quite the roll in the 70s, being absolutely fearless as he lambasted everything in his path. It’s this sort of fearlessness that makes Young Frankenstein such a triumph, and while it’s not the best of what Mel Brooks ever offered in the form of a comedy, it comes pretty damn close.
Best line: “You have to remember that a worm… with very few exceptions… is not a human being.”
26. Sixteen Candles (1984) Directed By John Hughes
As I get older I treasure the long list of films that could no longer be made in today’s overly-sensitive times, and there are none better than “Sixteen Candles”. If you’re young and new to this film, you might be surprised to know this film was rated PG in its day, and it made sense if you had an ounce of maturity to you — you’ll just have to watch the film to determine what you think of how the ratings boards have changed over the years. As time goes on and I rewatch John Hughes movies, one thing remains the same in my hall of opinions, and that is this: “Sixteen Candles” stands true as Hughes’ most dedicated comedy. The film is gleefully free of Hughes’ later boring tropes of musical montages and morality tales (for the most part). Instead, it zeroes in on being a beacon of raunch, uninterested in whether it offends or not, but rather focusing on a more sophisticated audience who can tell the difference between being racist and using race to prop up a joke. There’s an important difference to be had there, and one that has gone misunderstood in newer generations. As a comedy, there isn’t much to dislike about “Sixteen Candles”.
Best line: “What the hell are you bitchin’ about? I gotta sleep under some Chinaman named after a duck’s dork.”
25. Best In Show (2000) Directed By Christopher Guest
As I crash into the top 25 I need to make my choices very wisely, and “Best In Show” is as solid a place to start as any. Of all the Christopher Guest-directed “mockumentary” features, this one strikes me as the best as it captures all of the very greatest and quirky parts of the actors participating in it. There’s nary a joke that goes bad, from two left feet to songs about nuts to the never-ending LL Bean catalog. The beauty of the comedy with “Best In Show” lies in all of the little details, but having a perfectly backdropped staging of OCD dog owners running amok to feed their own egos, even at the expense of their pets, is beautiful ground for satire. Guest homes in on this fact and delivers his best film, and Eugene Levy and Catherine O’ Hara calmly throw down their greatest acting performances, which as we all know, is saying a hell of a lot.
Best line: “Now tell me, which one of these dogs would you want to have as your wide receiver on your football team?”
24. A Christmas Story (1983) Directed by Bob Clark
This is the greatest Christmas movie ever made, and that’s all there is to it. For those of us who grew up in a certain time and knew we should be excited about the holiday season, but couldn’t help but be stressed out and anxiety-ridden over all that it inevitably would bring, this film is the only antidote. Holidays never quite go the way you wish they would, but this film recognizes there is magic in all of the little imperfections we see on a daily basis with our own families. Most of us hold our breath through the holiday season, accepting the fun with the insecurities, and no other holiday film seems to understand this balance better than “Christmas Story”.
Best line: “He looks like a pink nightmare.”
23. Airplane! (1980) Directed by Abraham and The Zucker Brothers
How do you even count how many times you gut laugh during “Airplane!”? Is it even possible to quantify the giggling that occurs during its 90 minute run time? The beauty of this film is in its glorious one-note serenity, proving that, if you’re smart enough, you can carry a single idea throughout the entirety of a film’s running time, then drop the mic leaving the audience somehow wanting even more. There have been countless movies that have tried to cash in on the glorious brilliance of “Airplane!”, trying to match the jokes, equal the perfect rhythm, and realize the affected performances, and few have even come remotely close. Cherish this film the way it should be cherished, and it will undoubtedly return perpetual dividends.
Best line: “Don’t call me Shirley.”
22. Election (1999) Directed by Alexander Payne
I can’t think of many performances better than Reese Witherspoon’s in “Election”. Her beautiful dedication to making the audience absolutely despise Tracy Flick is nearly unparalleled, and her selfless vision of making the character completely despicable in nearly every way is a document to how this woman is one of the best to ever grace the screen. Matthew Broderick as the conflicted every man who has unique demons holds his own with Witherspoon’s powerhouse performance, and Payne keeps it all in check with his masterful writing and direction. This is a film truly made for adults, by adults, and it should be celebrated as a gifted rarity in modern cinema.
Best line: “You’ve given me so many things, like good health, nice parents, a nice truck, and what I’m told is a large penis, and I’m very grateful.”
21. Napoleon Dynamite (2004) Directed by Jared Hess
What works best in “Napoleon Dynamite” is that it doesn’t judge. It doesn’t pontificate. It doesn’t ask us to look past what its characters are saying and doing. It’s merely a snapshot into a cast of colorful human beings placed into an Anywhere, USA, struggling over quesadillas and broken coccyx’s. It’s very dreamlike in its way, creating an almost ethereal and meditative mood as it chooses to observe rather than interject. Sometimes the smartest thing to do is step back and let the comedy happen as it carries you into the sky and floats you down into the sand dunes, where footballs can be thrown over mountains and dance moves can earn undying respect.
Best line: “What do you wanna bet I can throw this football over them mountains?”
20. Friday (1995) Directed by F. Gary Gray
Those of you who think it’s more or less impossible to create a perfect comedy that has constant laughs and brilliant performances, I point you to “Friday”. The revolving cast of characters in this film is so irrefutably perfect that it’s nigh-on impossible to find a single flaw inside a story that’s very simple. Besides being the ultimate stoner movie (which it absolutely is), it’s the king and queen of hang-out movies, an experience that makes you feel so good that watching it for the 500th time only makes natural sense. “Friday” is arguably the most consistently hilarious movie ever made, where I could recite every line by memory, and that’s only because I’m able to relax every neural pathway in my brain while watching it, completely closing out all of the extraneous noise of the real world beating down my door. It transports me to another planet, stoned or not, and isn’t that what great cinema is all about?
Best line: “Don’t nobody go in the bathroom for 35 to 45 minutes.”
19. MacGruber (2010) Directed by Jorma Taccone
I was totally prepared to hate this movie. If there’s one thing I automatically know about SNL skits turned into movies is that they are going to inherently suck balls. By the time the credits rolled with “MacGruber”, I was convinced I had torn my rib cartilage from laughing so hard for so long. This movie works because Will Forte understands that, with a concept as ludicrous as this, you can’t waste a single second winking at the camera and laughing at your own jokes which is something SNL content is dreadfully infected with. He goes balls-to-the-wall with MacGruber, completely dedicating himself to the character, and taking the psychology hilariously serious. MacGruber is an absolute fucking mess of a character, and Forte takes it to the extreme and back again. The movie also works because it’s absolutely filthy; making a PG-rated romp as most SNL projects would only serve to insult an audience expecting much more. No matter how long you wait for this film to fall apart under its own satiric weight is a fruitless journey — in fact, “MacGruber”s magic is its long-lasting power to exist in a completely unique world. The death scene of Dieter Van Cunth is worth the price of admission alone.
Best line: “Fuck you, dude!”
18. Coming To America (1988) Directed by John Landis
There’s never a bad time to watch this gloriously hilarious movie, whether it’s winter or summer or during a tornado. It just always makes sense. Landis came on board to work with Eddie Murphy again, and somehow, they were able to completely film this movie in under a month. That’s pretty astounding considering all of the nuance and directorial flourishes you experience while watching this flawless film. “Coming To America” is Eddie Murphy’s idea, and you can see why he’s at his best when he’s able to just let loose and carry a character. Murphy is also smart enough to just step back and let his supporting cast do their thing, but this is Murphy’s movie, and it’s all the better for it. Not even the woefully terrible sequel could tarnish the exalted legacy of this bona fide classic. 35 years later, I’m still quoting this movie, and probably will be for the next 35 years.
Best line: “Hey, Stu, your rent’s due, muthafucka!”
17. South Park (1999) Directed by Trey Parker
Few movies are uncompromisingly funny as “South Park”, and it was a blast of fresh air to see an unedited version of the classic TV show back in 1999 when this dropped. This movie came at the end of an era where the mantra of “nothing is sacred” was still a thing to cherished. Comedies in our modern times are watered-down snowflake fests for the most part, and I deeply appreciate “South Park” in its ability to be incredibly intelligent while not caring about who it offends all at the same time. Only a few comedies in history have been able to pull off the brilliant balance of low-hanging-fruit boneheaded-ness with off-the-charts intelligence (keep reading for the masters of this feat), and “South Park” is unquestionably one of them.
Best line: “Fuck, shit, cock, ass, titties, boner, bitch, muff, pussy, cunt, butthole, Barbra Streisand!”
16. The Blues Brothers (1980) Directed by John Landis
As I typed “Blues Brothers” just now, I came to the realization that I have now come to the pantheon of truly brilliant comedies as I have formed them in my mind. This is a film in truly rarified air, that stands alone in both originality and execution. The combination of two of the most brilliant comedic actors in history playing off of each other perfectly certainly doesn’t hurt, but having a visionary director starting to solidify his obscenely high standards doesn’t hurt things either. There aren’t many times in film history where an epic comedy has worked, but “The Blues Brothers” is a beautiful exception. Dan Aykroyd’s genius in writing a massive script of 324 pages was only challenged by John Landis’ ability to whittle it down into a practical running time that still ran at two and a half hours with absolutely no filler. Think about it: can you recall a comedy that was this long that didn’t bore the living shit out of you? Of course you can’t. Landis is a master of formulating drama and action throughout his comedy work while Aykroyd and John Belushi were every bit as brilliant in coming up with inventive ways to be fantastic actors above all else. This is simply one of the greatest films ever made in any genre.
Best line: “I know all about that stuff, I have been exploited all my life.“
15. Blazing Saddles (1974) Directed by Mel Brooks
“Blazing Saddles” is a movie that has meant many things to me over the years. When I first saw it as a kid, I viewed it as yet another vehicle for the wonderful Gene Wilder to occupy my life. As time has gone on, though, I’ve begun to appreciate it for the extinct artifact it has become. In our woefully boring woke times, this is a film that wouldn’t be conceived, much less produced. Personally, I get offended when I see old filmmakers like Brooks or whomever extolling the virtues of current mores, and even lambasting their own work from the past because current societal norms have deemed things “inappropriate”. I would argue that 2023 is the perfect time for audiences to place their linearity to the side and enjoy a different take on what makes a nation racist, homophobic, or intolerant to begin with. “Blazing Saddles” is a very rare document where these hot-button topics are defused by confronting these uncomfortable topics head-on rather than trying to sweep them under the rug, pretending they don’t exist. In our current times, where people are celebrated for extolling an insular mediocrity, “Blazing Saddles” was unafraid to make people uncomfortable by facing off with the shit we choose to ignore. This film is actually one of the greatest testaments to solidified anti-racism you’ll ever see, and if you’re unable to appreciate this fact, you’ve got a serious problem. It also has the greatest fart scene of all time which is just a tasty cherry on top.
Best line: “Could you repeat that, sir?“
14. Monty Python And The Holy Grail (1975) Directed by Terry Jones and Terry Gilliam
Remember when I was talking about being woefully dumb and highly intelligent all at once to create something truly brilliant? Yeah. These guys. Monty Python created a new experience with their comedy, unafraid to put their huge brains aside when they needed to, but only long enough to swing it back to some of the most high-brow comedy you could ever imagine. You don’t have to be dumb to appreciate physical comedy or toilet humor, but why be stupid about it? This is a much harder thing to pull off successfully, and “Holy Grail” is one of the most gloriously smart movies we’re ever likely to see in our lifetimes. This might not be the Python’s best movie, but when you’re this talented it doesn’t even matter.
Best line: “Oh, please let me face the peril!”
13. The Naked Gun (1988) Directed by David Zucker
I just laughed typing “Naked Gun” — that’s all it took. It’s hard to imagine that David Zucker could make a movie funnier and more creative than Airplane!, but he certainly did with “The Naked Gun”. I have to be careful and prepared each time I decide to watch this movie because I know I’ll be exhausted with laughter when I’m done. What I love most about it? The characters aren’t being funny. They’re just reading their lines. Sometimes in comedy you gotta just stop trying to entertain and give yourself to the written page. Leslie Nielsen is absolutely perfect as the straight-faced dope, never gurning for the camera, letting the absurdity of his surroundings carry the weight of the comedy all around him. Smart and straight-faced slapstick seems to be a thing of the past, and “The Naked Gun” is a relic of a much better time in comedy.
Best line: “You got something on the side of your face…no, the other side.”
12. Revenge Of The Nerds (1984) Directed by Jeff Kanew
Listen, if you were an 11-year old boy in 1984 and you saw “Revenge Of The Nerds”, you would have just seen the greatest comedic achievement in your young life. It’s only an extra added bonus that this film has aged beautifully. “Nerds” has taken some heat in recent years for being insensitive and offensive, and I say, good. “Nerds” is a snapshot of its time. Things were played for laughs back then, and it’s not up for modern audiences to make any sense out of it. Only the most deeply unhumorous people could shy away from the hilarity this movie brings, and I feel sorry for those who can’t lighten up and enjoy the intensely inventive atmosphere this movie presents. It’s laugh-out-loud funny from start to end, contains great performances, and even makes us feel good at the end. It also foresaw the dawn of the nerds inheriting the earth, leaving the meatheads and dipshits trailing in their four-eyed wake. Skip this movie at your own peril, and if you’ve seen this 1,000 times already as I have, go watch it again; you know you want to.
Best line: “What the fuck is a frush?”
11. Borat (2006) Directed by Larry Charles
I’m not sure I’ve ever laughed harder in my life. The balls of steel on this Sacha Baron Cohen should not only be appreciated, they should be worshipped. The undying and fearless dedication this man possesses to achieve a laugh is something I will forever be in awe of. If ever there were a more scathing, yet accurate, skewering of America, it is “Borat”. Enough said.
Best line: “I arrived in America’s airport with clothings, US dollars, and a jar of gypsy tears to protect me from AIDS.”
10. Pee Wee’s Big Adventure (1985) Directed by Tim Burton
Pee Wee absolutely needs to start off my top ten as this is one of those zeitgeist moments of my youth as I came to appreciate film and all its power. “Pee Wee’s Big Adventure” created it’s own little world and invited us in, and either you were on board, or you weren’t. If you chose to participate, you were treated to an inventive slice of artful precision, inspired and wholly original. Known to be Tim Burton’s first feature, it also should be mentioned that this was written by Paul Reubens and the late great Phil Hartman, the greatest SNL player of all time. Hartman and Ruebens went way back to the 70s in terms of their relationship, and the convergence of styles and creativity with Burton produced one of the greatest and most pure comedy worlds ever created. This film simply stands as a timeless classic, an experience that doesn’t exist in any time zone, forever welcoming its viewers into a recess of our minds that is beholden to nothing but laughter.
Best line: “Let’s talk about your big but, Simone.”
9. This Is Spinal Tap (1984) Directed by Rob Reiner
What can I possibly say that hasn’t already been said about “Spinal Tap”? What I love about this movie is how my favorite scenes and band members seem to shift over time. When I first saw it back in the 80s, Nigel Tufnel was my favorite, the moody, insulated prima donna, defensive with his manner and dismissive of everyone. Then when I approached my 30s, it became David St. Hubbins that impressed me, big and bombastic, charismatic and mysterious, and ultimately unreachable. As I’ve cruised through my 40s and approached my 50s, however, it’s Derek Smalls that I relate with the most. The forgotten member, trapped in an egg he’s desperately trying to clamber out of, but realizing that he’ll forever need to be happy with his back seat position as he attempts to not knock over his miniature version of Stonehenge. Harry Shearer is the greatest anyway.
Best line: “I feel my role in the band is to be kind of in the middle of that, kind of like lukewarm water.”
8. Trading Places (1983) Directed by John Landis
“Trading Places” is one of those rare moments in cinema where everything comes together, no matter how many things you try and stuff into it. With a stellar ensemble cast, things can, and often do, go wrong — egos and personalities and pride will usually destroy any onscreen chemistry required to keep a movie afloat. Luckily for us, John Landis was able to keep it all together brilliantly and deliver his greatest filmic achievement, which is saying one hell of a lot. To understand the massive momentum of this movie you have to also consider the meteoric rise of Eddie Murphy at the time, not to mention the huge popularity already cemented from Dan Aykroyd. Also throw in Jamie Lee Curtis, Don Ameche, Ralph Bellamy, Al Franken and Denholm Elliott and you have a recipe for disaster if not handled with care. The reality is, “Trading Places” is a beautiful testament of how tons of big personalities can come together to deliver an absurdly high-end result. The performances of Aykroyd and Murphy dance off each other, leaving just enough room for Landis to sprinkle in the details that truly make the movie stand out. And goddamn, is it funny. For me, the magic of this film lies with Aykroyd’s performance, though. He accomplishes one of the finest acting achievements in a comedy I’ve ever seen, going through some real dynamic changes whilst simultaneously not progressing his general demeanor at all. By the end of the film he’s essentially the same uptight son of a bitch he’s always been, but just a smidge more wise. Our personalities don’t change overnight, if at all, and for Aykroyd to illustrate this factoid of our mortal coils is one of the great testaments to movies everywhere.
Best line: “When they brought you in here and booked you, you was cryin’ like a pussy. YEAH.”
7. Raising Arizona (1987) Directed by The Coen Brothers
As you’ve probably noticed, I’m big on movies that create their own worlds for me to dive headlong into, and “Raising Arizona” is one of those timeless dreamlike states that you can either accept or decline. Beside all that, though, it’s simply one of the most hilarious goddamn things you’ll ever watch. Countless gags, endlessly quotable, and brilliantly constructed, this was the Coens starting to ramp up their hold on strikingly unique filmmaking. At the time this was released we weren’t accustomed to that dark edge of the Coens we’ve learned to know and love, and “Raising Arizona” was a massively influential bomb of a film that changed many of us forever. I always thought this movie was like Road Warrior meets The Three Stooges, and that is in no way a knock — Barry Sonnenfeld made sure this flick flung along at a rapid fire pace with a visual pizazz that blew minds. Along with being hilarious, it was also pretty deep on its own merit, showing that its characters can naturally evolve within a relatively short run time of 98 minutes. “Raising Arizona” still gives me the chills.
Best line: “That Rupert’s a sly one…he already knows his ABC’s.”
6. Brazil (1985) Directed by Terry Gilliam
Whenever people ask me what my favorite movie of all time is, I reflexively say “Brazil”, and that is more or less true. But we’re talking comedies here, and while I do find “Brazil” to be hilarious, it’s also a lot more than that. Focusing on just the comedic aspects of the film, it’s hard to find a darker and more dreary commitment to humor. Gilliam has made it clear over the years that his vision of what’s funny lies in the cloudy hues of human foible, and the drastic creations of people’s desires are the most purely evil inspirations for comedy. It’s an intricate balancing act that Gilliam has teetered on his entire career, and “Brazil” is the greatest manifestation of this idea. “Brazil” is Murphy’s Law wrapped inside 100 other boxes filled with Murphy’s Law, presented to a careerist unable to understand what it even means to live in a world where Murphy’s Law is a conceptual reality. The humor of “Brazil” lies in the conceit that Sam Lowry cannot comfortably exist in this world, and because of this, we shall laugh at his misfortune. Why do we laugh? Because we’re Sam Lowry. All of us. And if we can’t cry at our situations in life, we laugh. What else is there, for Christ’s sakes?
Best line: “Confess, will you? If you don’t you could jeopardize your credit rating!”
5. Office Space (1999) Directed by Mike Judge
The movie that just keeps on giving. It never gets old. Perpetually relevant. And perfect in its place amongst comedies. Anyone who has ever worked (and that’s all of us) can easily and deeply gravitate to the tones and waves of this film’s message. The movie doesn’t always work in terms of flow, but it doesn’t matter because we’re resonating so deeply to our own connections with this flawed little slice of hell it encapsulates. Judge will be forever judged by Beavis and Butthead, but “Office Space” is his true masterpiece.
Best line: “Watch out for your cornhole, bud.”
4. Life Of Brian (1979) Directed by Terry Jones
This should go without saying, really. The smartest lambasting of organized thought and religion ever produced, and even more relevant now, nearly 50 years after its birth. This film isn’t at all interested in attacking the central religious figure of our history, but more the people who choose to invest in blind faith to begin with. It hacks away at the idea that the believers who think they’re true individuals are blinded and crippled at the notion that their lives may be as empty as their own heads. It’s the heretical nature of “Life Of Brian” that resonates, not because this notion is fascinating in itself, but because the targets of this heresy are too dim to understand it anyway. It’s no surprise this is one of the most controversial films ever made even despite the fact that Christ is never made to be the butt of one single joke. If you ever need a litmus test of one’s intelligence, ask them if they love “Life Of Brian” or not.
Best line: “The shoe is a sign that we must gather shoes together in abundance!”
3. The Jerk (1978) Directed by Carl Reiner
Few movies in my life lift up my spirits and take me to another netherworld of pure joy and happiness, but “The Jerk” is definitely one of them. Steve Martin is one of the great comedic treasures in existence, and “The Jerk” only serves to project his ability to be dumb and brilliant in operatic levels of creativity. Like his peers in the Monty Python group, Martin tightropes a fine line between high and low brow worlds, but he proves it takes an acerbic wit and otherworldly talent to appeal to both. “The Jerk” is arguably the best example of this in the world of comedy, and we are all better for its existence.
Best line: “Is grandma still farting?”
2. The Big Lebowski (1998) Directed by The Coen Brothers
Well, you knew this was coming, right? The big one. THE one. The most quotable movie of all time. The movie even your lame, uptight parents love. Sometimes a movie just breaks through all the veneer, captures a generation, then continues to capture each and every generation after it. “The Big Lebowski” is that movie. This movie wasn’t a big hit when it came out oddly enough, and perhaps it’s because The Coens followed up “Fargo” with “Lebowski” and it confounded audience expectations. Whatever the reason that critics didn’t dig it, it made an instant impression with me, and I can remember sitting in an empty theater with a date at the time literally suffocating with laughter. My date didn’t think it was all that funny — we didn’t last long. The greatest comedy of all time? Depends on my mood, but sure, I think it is. What’s better?
Best line: “Dude, err, tomorrow is already the 10th….far out, man.”
1. Dr. Strangelove (1964) Directed by Stanley Kubrick
Even though I wasn’t alive at the time of its release, it’s tough to imagine a comedy changing the landscape more than “Dr. Strangelove”. The fact it’s still cutting edge today nearly 60 years later proves its longevity and staying power. Movies simply did not exist like this back in 1964, and come to think of it, they haven’t existed like “Dr. Strangelove” since. This is a once in a millennium moment in artistic freedom, and “Strangelove” was merely setting the stage for one of the most frighteningly relevant and powerfully poignant trio of films by a filmmaker the world has ever seen. Earth still wrestles with what this film makes fun of, and I’m not sure I’ve ever witnessed another film that tiptoes through such disaster with such comedic grace and timing. Of course, it’s easier to accomplish this when you have Peter Sellers as your lead, which I think is the greatest performance of all time, comedy or otherwise. Sellers simply astounds with his timing, rhythm, levity, seriousness, body language and strangeness, completely levitating an already lofty movie into the stratosphere. George C. Scott has his work cut out for him opposite Sellers, but he delivers in a big way himself, letting his precise delivery of lines and body movements carve out its own little slice of perfection. This is the first modern Kubrick experience as we know it, and to say “Dr. Strangelove” is anything less than unbridled genius is a massive understatement.
Best line: “I am capable of being just as sorry as you are!”
Occasional Feel Good 