21 Jump Street (2012)

So many things shouldn’t work here.  Big-screen comedies based on semi-serious TV shows almost always reek of rotting TV Guides (Wild Wild West, Baywatch, The Dukes of Hazzard). And who in 2012 was looking at Channing Tatum and Jonah Hill and thinking “buddy comedy”?  But the duo had killer chemistry, the movie wickedly skewered action-comedy tropes, and the bad guy was a clean-cut vegan. So here we are, talking about one of the most riotous comedies of the young century. We kept trying to talk ourselves out of it, but the sheer volume of insane drunken laughs brings 21 Jump Street in at #40.  

Napoleon Dynamite (2004)

Gosh!  Napoleon Dynamite is a movie with incredible skills (nunchuck, bow-hunting, computer hacking, et al), a feel-good underdog story both in its nerdy-guy-gets-a-life plot and its incredible rise from no-budget indie to comedy blockbuster. Unknown Jon Heder created one of those comic characters that you instantly recognize yet this very particular kind of goofball hadn’t yet found his way to the big screen. We love Napoleon for its shaggy-dog earnestness and for its filmmakers’ ability to resist a sequel.  This one was perfect as is. (Yeah, yeah, we know there was a animated follow-up but you know what we mean.  Are you going to eat those tots?)

What We Do in the Shadows (2014)

“When you’re a vampire, you become very sexy.”  Right!  Now could somebody have told Tom Cruise before he mangled Interview with the VampireShadows’ algebraic formula tells you everything you need to know -- Taika Watiti plus Flight of the Conchords times bloody laughs equals an instant classic.  If you’re a fan of the What We Do In the Shadows TV series and its story of the Staten Island undead, do yourself a favor and check out the original blueprint here. It’s the movie that invented the horror-mockumentary, a genre we didn’t know our immortal souls hungered for so desperately. 

Clueless (1995)

Amy (Fast Times at Ridgemont High) Heckerling throws another teen-comedy fastball right down the middle with this 90s update of Jane Austen’s Emma. Alicia Silverstone graduated from Aerosmith videos to deliver the best performance of her career as the rich and clever Emma … er, Cher. If you’ve read the Austen novel, you’ll appreciate how faithful the adaptation is, and boggle that its romantic twists and subplots translate so seamlessly into late 20th-century shopping mall culture.  Clueless is also the movie where most of us met the eternally likable Paul Rudd, who to be honest is kind of a better-Baldwin.

Shaun of the Dead (2004)

Another horror comedy? For God’s sake, yes, another horror comedy. Edgar (Scott Pilgrim Saves the World) Wright makes his second appearance on our top 50 list with a comedy that recognizes the inherent ridiculousness of zombies. Blank-eyed dullards bleating “Aaaaaaeeeerrrrgh!” as they shuffle down the street? Come on! But that doesn’t mean Shaun of the Dead doesn’t have scares -- its jittery balance of bloodstained horror and outrageous laughs is one of its best qualities. Shaun’s central plot conceit might also be its best joke -- if zombies actually were shuffling around our modern cities, would we even notice?

The Wedding Singer (1998)

Happy Gilmore, Billy Madison, and The Waterboy may have more stupid laughs per minute, but The Wedding Singer is Adam Sandler’s best stab at an actual movie with real characters we care about.  Don’t get us wrong, it still has the stupid laughs, with its 1985 setting providing fodder for “weren’t we ridiculous?” hair, clothes, and music gags. Along the way, we discovered that Sandler had palpable comic chemistry with Drew Barrymore, fizzy alchemy that they continued to exploit in 50 First Dates and Blended.  Not sure that aficionados think of Sandler/Barrymore as one of the great romantic comedy couples but maybe we should. 

Kung Fu Hustle (2004)

A hilarious comic book movie that wasn’t based on a comic book, a live-action Looney Tune where the laws of physics are thrown through a plate-glass window in the name of comedy.  In a more just world, Stephen Chow would be a household name -- he wrote, produced, directed, and starred in this stylish, goofy tour de force. Like his earlier Shaolin Soccer, Kung Fu Hustle is full of visual flourishes that only enhance the jokes. It’s Enter the Dragon meets the Roadrunner -- and who wouldn’t want to live in a world like that?

A Fish Called Wanda(1988)

A Fish Called Wanda features a gathering of comedy stars at the peak of their powers:  John Cleese, Jamie Lee Curtis, Michael Palin, and a performance from Kevin Kline that landed him the ultra-rare comedy Oscar.  Cleese in particular has never been better -- like Wanda does to his Archie character, Curtis unlocks some authentic human passion in the too-uptight-to-sneeze comic that we’ve never seen before or since. The tension between the loud, obnoxious Americans and the stifled, repressed Brits delivers a fish tank full of trans-Atlantic laughs.  

The Big Lebowski(1998)

Can’t a guy just replace his rug?  Casual runs deep in The Big Lebowski, a movie that’s simultaneously laid back and out of control.  This is the Coen Brothers in their Raising Arizona screwball mode, scrambling a film noir plot with a gaggle of wackadoodles from the part of town you never visit. This gem perhaps isn’t as laugh-out-loud funny as others on our list, but like the Dude himself, The Big Lebowski abides.  It also narrowly edges out Kingpin as the best bowling comedy of the past 50 years. 

Dazed and Confused(1993)

A rare nostalgia movie that sees life as it actually was, rather than an idealized version of a youthful past. In the words of one young character, the 1970s obviously suck.  It’s Richard Linklater’s smarter, funnier, period version of his indie classic Slacker -- heavy on character with little attention to plot, at least not the formulaic three-act stuff they teach you in film school. Like Fast Times, Dazed and Confused is virtually bursting with unknown performers who would go on to rule Hollywood, including Matthew McConaughey, Ben Affleck, Renee Zellweger, and Parker Posey.  This is a movie best enjoyed with a prodigious amount of beer, but no matter how you watch, it’s definitely alright, alright, alright.  

For more of the best comedy movies, be sure to check out:

50 Best Comedy Movies of the Past 50 Years, 50-41

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