First thing first: this is not a perfect list. Humor is the most impossibly subjective quality of movies to quantify, and what I might find hilarious might bore you to death. Vice versa, there are some classic comedies that I didn’t include on this list, most notably Ghostbusters and Groundhog Day. It’s not that they are bad films, just that I found them about as funny as a fly in my soup. And the soup was poisoned. And I hadn’t eaten in five days. Besides, I just love Bill Murray much more as a serious actor.
You will also notice that the list is dominated by movies from the past 30 years, but what can I say? Laughs expire quicker than art. I also kept the list down to one per staple, since I didn’t want to clog the list with every Judd Apatow film. Without further ado, and in no particular order, I give you: the 20 funniest movies of all time.
There’s Something About Mary
Roger Ebert once recalled that this was the only movie he ever attended in which someone in the audience fell of his chair from laughing. My own reaction to it, even the second time around, was hardly more dignified or less physical (I literally laughed myself to tears). Diaz has never been funnier again, while Stiller has (to my mind) never been funny at all after this. But if lighting only strikes once, it surely strikes hard.
The Monty Python Trilogy
“If you have to ask what jazz is, you’ll never know”, Louis Armstrong once quipped. The same goes for the humor of Monty Python: if you don’t laugh, there is no way in hell anyone will be able to explain the joke – because, well, there isn’t one. They ended sketches by having a knight hit people over the head with a rubber chicken, by having a policeman come in to proclaim the whole affair “far too silly” or just by breaking out of character and saying “this isn’t going anywhere, is it?” to each other. The dispute about which or their films is the best is as pointless as it is silly: all three are hilarious and essential viewing for everyone ever.
The Pink Panther Strikes Again
I have a very infantile love for the Pink Panther series, but there is a definite quality to the movies besides the fact that they made me piss my pants as a kid. Peter Sellers is often regarded for his brilliant high-brow impersonations more than for his physical comedy, but he excels in the latter as well. Combine that with some great set-pieces (a scene in which Sellers’ character tries to cross a moat is especially memorable) and one of the best sidekicks of all time, and you have an absolute winner.
Some Like It Hot
After seeing this movie on every “best movies ever” list there is, you might forget just how exasperatingly much fun this movie is. The script is fantastic, the two leads are absolutely killer in high heels and Marilyn is sexier than ever. Billy Wilder was a master in making his films both really good and really funny, and he is on top of his game here. The Apartment is even lovelier, but has fewer laughs.
There is a chase scene at the beginning of Charlie Chaplin’s The Circus that is so pitch-perfect in set-up and execution that it gives every comedian (with the possible exception of Buster Keaton) something to look up to on the front of physical comedy. While this is not Chaplin’s best film (Modern Times probably takes that honor) or even his most lovable one (without a doubt The Kid), this is probably the one with the most laughs.
Anchorman: The Legend of Ron Burgundy
Imagine all the comedy of an entire season of The Office – a good season of The Office – put together in a 90-minute movie. If that mental image has very little room for a plot or coherence, you might understand the sheer insanity of Anchorman. The plot of the movie is maybe given of five minutes of screen time, and the rest is filled with Steve Carell, jazz flute, Steve Carell, the scientific proof why women can’t be anchormen, Steve Carell and the most glorious leading mustache in all of the cinema.
At the end of Clerks II there is a scene so gloriously over-the-top, so incredibly out-grossing and so fantastically hilarious that it might distract from the fact that at it’s heart, it’s actually a really good movie. There is a lot of thought about both Smiths style of filmmaking and the film universe that he created, and it wouldn’t be too much of a stretch to consider the movie as a career thesis statement. Oh, and someone fucks a donkey.
Judd Apatow & compatriots have given us some great movies in the past years, (almost) all of which could be included in this list. But Superbad is the one that gets my vote, probably because I find it most relatable. Make of that what you will.
The Naked Gun
Beating down on Leslie Nielsen’s style of comedy from the perspective of a serious film critic is easy, but why bother? The Naked Gun‘s humor might be silly to the max, but it’s also incredibly inventive and you have to give Nielsen’s fantastic comic timing credit.
This entry is mostly based on the first twenty minutes of the film, which kicks off an avalanche of idiocy (including the most original meet-cute of all time) under a gleeful score of yodeling folk music. That the rest of the movie is mostly spent resolving the problems set out in the fantastic opening shouldn’t take away the fun. There’s always Nic Cage’s hair to laugh at, after all.
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