In my final list before my new and improved Top 10 of all time, here is a list of the funniest movies I have ever seen. Of course comedy is as subjective as any form of art, so my list is probably going to differ from just about everyone else’s. This is one of the hardest lists I have had to compile. It is a mix of laugh-out-loud movies with great films that are comedies. AFI’s list of laughs was topped by two movies in Colin Cowherd’s favorite comedy genre: Some Like It Hot(1959) and Tootsie (1982). Following those in the top 10 were the likes of Dr. Strangelove (1964), Blazing Saddles(1974), and Airplane! (1980). Are any of those on this list? You will have to keep reading and find out…
Blind spots (notable unseen films): The Blues Brothers (1980), Coming to America (1988), Marx Brothers movies, The Odd Couple (1968), Super Troopers (2001), Trading Places(1983)
Others receiving votes: Ferris Bueller’s Day Off (1986), A Fish Called Wanda (1988), Knocked Up(2007), Some Like It Hot (1959), This Is Spinal Tap (1984)
10. Animal House (John Landis, 1978)
In what is considered the granddaddy of all slime-ball comedy, Animal House can still deliver the laughs 35 years later. The characters are outrageous, the situations are ridiculous, and the screenplay is not much to speak of. The thing that makes the movie so funny is the fact that it does not care that it is not art. It never takes itself seriously, which results in the audience being able to just sit back and howl at its hilarity.Funny Quote
Otter: “Bluto's right. Psychotic, but absolutely right. We gotta take these bastards! Now we could do it with conventional weapons, but that could take years and cost millions of lives. No, I think we have to go all out. I think that this situation absolutely requires a really futile and stupid gesture be done on somebody's part!”
Funniest Character: Bluto (John Belushi)
9. Sullivan’s Travels (Preston Sturges, 1941)
While this may not have the volume of laugh-out-loud moments as many other films on this list, it is certainly one of the elite comedies ever made. It is so sharply-written, filled with bits that are certainly tailored to that era yet are still humorous today. It is the most important, ironic, and brilliant film about the Great Depression made during that period. Oh, and it spawned the idea for O Brother, Where Art Thou?, whose connection to Sullivan’s Travels is as funny as anything in that actual movie.Funny Quote
Sullivan: “Aw, what do they know in Pittsburgh…”
LeBrand: “They know what they like.”
Sullivan: “If they knew what they liked, they wouldn’t live in Pittsburgh!”
Funniest Character: John Lloyd Sullivan (Joel McCrea)
8. The 40 Year Old Virgin (Judd Apatow, 2005)
Even though I consider Knocked Up to be a slightly better movie, this one actually has the more sustainable laughs. There is not a single character that is not hilarious at some point. This actually feels less like a movie and more like a story brought together by improv sequences by a cast that was born for one another. When there is never a false note with a joke reflex as widespread as this film has, you know you are in for a comedy classic.Funny Quote
Andy: “Yeah, I’m not a big ho-runner.”
David: “My uncle used to drive a ho-runner.”
Funniest Character: David (Paul Rudd)
7. Love and Death (Woody Allen, 1975)
This is by far Woody Allen’s funniest and most ridiculous movie. It features a slapstick side of his humor that is rarely expressed in his movies. It still has the interesting, quick-witted conversations and punch lines, but this movie’s plot and execution are absolutely absurd. It is a riot from start to finish, and certainly the one great Allen flick that far too few people have seen.Funny Quote
Boris: “You’re a tyrant., and a dictator, and you start wars!”
Napoleon: “Why is he reciting my credits?”
Funniest Character: Boris (Woody Allen)
6. Superbad (Greg Motolla, 2007)
There has not been a comedy in the last 10 years that I could watch more consistently than Superbad. It is endlessly inspired and hilarious. Seth Rogen and Evan Goldberg have established themselves as real comedic writers, and this stands as their best work. It is not a movie of obvious jokes or laugh checkpoints. It is a movie that is so nostalgic and true that everything comes off as being uproariously funny. Whenever it is on TV, I have to watch until the end. I just cannot get enough of Seth and Evan. One of my favorite comedic pairs ever.Funny Quote
Seth: “You know how many foods are shaped like dicks? The best kinds!”
Funniest Character: Fogell (Christopher Mintz-Plasse)
5. Grindhouse (Robert Rodriguez & Quentin Tarantino, 2007)
In our Top 10 the 2000s series, I ranked this this as the funniest movie of the first 10 years of the millennium. I still feel that way. Watching this in theaters was one of the greatest theater experiences ever. The mock trailers, the mix of the Tarantino and Rodriguez exploitation styles, and the gut-busting laughs at over-the top violence and insane dialogue make for movie-going bliss. I have never laughed more or had a more permanent smile on my face walking out of a theater.Funny Quote
Funniest Character: Stuntman Mike (Kurt Russell)
4. Dr. Strangelove or: How I Learned to Stop Worrying and Love the Bomb (Stanley Kubrick, 1964)
The more I watch this movie, the funnier it gets and further it moves up my all time list. Every line of dialogue is inspired. Every character is brilliantly written and effortlessly delivers laughs to the audience. Kubrick’s screenplay is so flawless that the character names are even punch lines. I am not sure if there will ever be another movie that will be even remotely like this one. It will leave some people slightly cold after watching it, but that mild admiration will eventually lead to downright addiction to the material. Seriously, it happened to me.Funny Quote
Muffley: “You're talking about mass murder, General, not war!”
Buck: “Mr. President, I'm not saying we wouldn't get our hair mussed. But I do say no more than ten to twenty million killed, tops. Uh, depending on the breaks.”
Funniest Character: General Buck Turgidson (George C. Scott)
3. Clerks (Kevin Smith, 1994)
In what I named one of my favorite on-screen pairs of all time, Dante and Randal are a comedic team unlike any other. Their awkward friendship and interesting conversations critiquing everything makes for one of the funniest experiences one can have during a movie. Clerks is a bit more subtle than Clerks II. The second chapter is a much more obvious form of comedy, but very few things compare to the original. The more familiar we get with Kevin Smith’s “Askewniverse” (I hope he is not serious about Clerks III being his last movie), the funnier this movie gets. Several movies have tried to be like Clerks, but it cannot be done. Smith’s characters are one-of-a-kind.Funny Quote
Randal: “Which did you like better: Jedi or The Empire Strikes Back?”
Dante: “Empire.”
Randal: “Blasphemy.”
Dante: “Empire had the better ending. I mean, Luke gets his hand cut off, finds out Vader's his father, Han gets frozen and taken away by Boba Fett. It ends on such a down note. I mean, that's what life is, a series of down endings. All Jedi had was a bunch of Muppets.”
Funniest Character: Randal Graves (Jeff Anderson)
2. South Park: Bigger, Longer, and Uncut(Trey Parker, 1999)
I realize that it may be a bit unfair to include a movie based on a TV show, but I couldn’t resist. This is probably the highest volume of laughs I have ever had. Every bit of this movie is offensive and hilarious. It is as good as anything the show has ever produced. It is maybe the best movie musical of the last 20 years. The characters that we have come to know and love over the years come to life in this movie with an edginess that cannot be expressed on the show. It takes its aim at everyone and everything that provides a target, and no one is left unscathed. Comic brilliance.Funny Quote
Cartman: “Hey Stan, tell them about the part where Terrence calls Phillip a testicle shitting rectal wart.”
Funniest Character: Cartman (Trey Parker)
1. Office Space (Mike Judge, 1999)
This is the most sustainable comedy I have ever come across. The subtlety of its joke delivery is unlike any other, so even when you have seen it a bunch of times, more things come up that are as equally funny as the obvious laugh points. The characters are all so believable and play it so straight that we cannot help but laugh our asses off at these people and their mundane lives, which are all too similar to our lives. Usually when a comedy is on some cable channel, it will depend on which part it is to determine whether I will watch any of it. This entire movie is one of those parts. There is never an off-note or a joke that doesn’t work. It is amazingly awkward and all too real. Mike Judge (whose Extract is quite underrated, by the way) is an absolute original, and I would love to see where Peter, Michael, Samir, and Joanna are nowadays.Funny Quote
Peter: “I can’t believe what a bunch of nerds we are. We’re looking up money laundering in the dictionary.”
Funniest Character: Michael Bolton (David Herman)
Thoughts? Comments? Anything I missed? I tried to make a well-rounded group, including at least one film of all my favorite types of comedy, with the unfortunate exclusions of Charlie Chaplin, Mel Brooks, Jim Carrey, the Coens, and Wes Anderson. Post your list and thoughts in the comments!
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