The 20 Best Comedy Movies of All Time

20bestmoviesThe funniest movies tend to burrow into our brains like no other form of popular entertainment. Through repeated viewings and earworm quotes, they create unconscious templates for life’s milestones and stopovers — dating, road trips, the college experience, marriage, the working world — and remind us of moments in time as well as entire eras. They’re comfort food and therapy, high art and cultural critique, nestled lovingly amid fart jokes and crotch punches.

The best comedy movies also enjoy a freedom that seems out of place in most other media, with run-times that allow them to develop complicated but self-contained worlds, the full buffet of acting, editing, and musical options, and the (frequent) R ratings that give them the appropriate range of artistic motion. “Comedy is subjective,” we’re constantly told. Maybe, but if something stays funny for decades it’s clearly reaching across cultures and contexts to tweak our collective nipples for a reason.

Here are our picks for the best of the best.

20. Office Space (1999)

Before Office Space, most people knew about Mike Judge’s crass but perceptive work via Beavis and Butthead, which only hinted at the multi-textured (if equally dude-centric) worldview of Office Space. Fortunately, most people can instantly relate to this terrifyingly beige universe in which TPS reports, mind-numbing repetition, and TGI Friday’s-style team spirit become the occasion for quietly absurdist field notes on corporate servitude. Select jokes, like David Herman (a.k.a. Michael Bolton) turning down his Scarface song when a black guy strolls past his car, turn lazy cultural role-playing into cutting social commentary. Most have become part of the lexicon. All have aged shockingly well.

19. Clueless (1995)

Often dismissed as a candy-coated time capsule of ’90s teen culture, Clueless is (as any true fan knows) a classic comedy of manners and social critique inspired by Jane Austen’s Emma. Let Heathers have the psyche-scarring and in-fighting; Clueless takes awkward, hormonal, status-obsessed interactions to sublime levels through heightened dialogue and a startling clarity of ideas. Many of the best comedies want to make sure you’ve seen their dark underbellies, but as Mean Girls and others have proven, laugh-out-loud films aren’t required to vibrate on a frequency of cartoon violence and subtle (or not) misogyny to make their marks.

18. Rushmore (1998)

Rushmore‘s humor is the slow-cooked kind, subtly spiced, but filling enough to warrant repeat visits. A million sad-sack high-schoolers, collegiate hipsters, and Holden Caulfields of all ages were validated by its miserable, self-obsessed characters and expertly curated soundtrack. Wes Anderson’s second outing also sharpened the art direction and dialogue from Bottle Rocket, but didn’t go bonkers with color coordination and cutesy affectations (as with pretty much everything he’s done since then). It’s the missing link between Harold and Maude and Scott Pilgrim vs. the World, a singular coming-of-age movie that never really wanted to grow up in the first place.

17. Anchorman: The Legend of Ron Burgundy (2004)

The ideal casting and chemistry of Anchorman’s leads would be wasted without the freedom to improvise or, later, the nimble editing that makes it such a surreal, gutsy film. Adam McKay’s post-Saturday Night Live directorial debut builds on the punchy and sophomoric charm of Will Ferrell’s turn in Old School, but dispatches with Todd Phillips’ mawkish character development. Compared to AnchormanOld School and most other comedies in general have a distressingly low jokes-per-minute count. Anchorman never tiptoes around a ludicrous set piece or sticks too close to a straitjacketed script to please an imagined demographic. Like Ron Burgundy himself, it just wants to be on you.

16. Wayne’s World (1992)

Oh, to see this film with fresh eyes. Mike Meyers and Dana Carvey’s finest cinematic moment (and SNL adaptation) proved so immediately influential and re-watchable that few people old enough to remember its release can muster the same guffaws these days. That shouldn’t take away from how skillfully director Penelope Spheeris played with audience expectations, turning non-sequiturs into running jokes and injecting the straight-faced lunacy of improv and sketch into a narrative, character-driven film. Only one comedy has ever done hard-rock clichés better than Wayne’s World (see below), and even that can’t boast characters as empathetic as Wayne Campbell and Garth Algar.

15. Pee Wee’s Big Adventure (1985)

If Pee Wee’s Big Adventure is the result of a couple of classic weirdos (Paul Reubens and Tim Burton) bonding over their shared tastes — as a standup buddy of mine once put it — it’s a truly epic bonding session. Of course, the impeccable art direction, cinematography, and performances don’t hurt. But as far as road-trip comedies go, few could stand up to the scene-by-scene analysis that Pee Wee’s Big Adventure easily does. Repeated viewings only reinforce how genuinely bizarre a character Pee Wee Herman is, or how deceptively simple the film’s pacing remains up until its surprise, Blazing Saddles-style meta-ending. Mostly, it’s a lesson in how infectiously positive worldviews never go out of style when rendered thoughtfully and artfully.

14. Ghostbusters (1984)

Ivan Reitman, Dan Akroyd, and Harold Ramis created something legitimately different for the world of Ghostbusters, which crackled with the goofy, horny overtones of previous Ramis/Bill Murray projects but found its footing in a very real, and very scary, Manhattan. Even kids, over whose heads most of the sex jokes flew, felt the power and presence of Ghostbusters’ Big Apple, which held profound consequences for our heroes’ actions and inactions. That makes it all the more impressive how director Reitman and his casually brilliant cast mine each situation for hilarity, putting to shame the lion’s share of other ’80s sci-fi/fantasy comedies (of which there were a bizarrely large amount, it should be noted). Despite Egon’s advice to the contrary, crossing the streams paid off handsomely, led in large part by Murray’s charismatic hucksterism.

13. Bringing Up Baby (1938)

It’s tempting to group romantic comedies of a certain age, especially the early 1930s through the ’40s, together even if they don’t share a lot of superficial traits. Still, there’s real kinship in the infectious, rapid-fire dialogue and class critiques of the screwball genre, at least as rendered by masters like Frank Capra, Howard Hawks, Preston Sturges and others. Screwball comedies helped defuse Depression-era tensions and anxieties, both external and internal, and set the standard for witty repartee. Between It Happened One Night and its numerous, handsome offspring, it’s almost impossible to pick a definitive example, but the script, acting, and astonishingly deft pacing of Hawks’ Bringing Up Baby, which features irresistible performances from Katherine Hepburn and Cary Grant, gives it a leg up on nearly all others. Despite initial criticisms that it was too derivative and loony, few films, comedic or otherwise, have proven themselves to be so ruthlessly efficient at charming first-time viewers.

12. The Great Dictator (1940)

The political satire of The Great Dictator is rooted in timeless notions of fascism and obedience, but its particular brand is so well-defined that it elevates Dictator above other examples of Charlie Chaplin’s physical genius. It may share a certain vaudevillian broadness with City Lights and Modern Times, but the fact that it was made before the world knew the extent of various Nazi horrors (Chaplin reportedly knew more than most, given his connections to Europe), only makes its third-act appeal for tolerance more poignant. Chaplin’s portrayal of Adenoid Hynkle (a Hitler caricature) is as bold as his hapless Jewish-barber character is affecting and sweet. “I always thought of you as an Aryan,” a Tomanian (a.k.a. German) commander says to the barber, who’s wearing a noose around his neck, about to be hanged from a lamp post by a gaggle of seig-heiling soldiers. “I’m a vegetarian?” he offers meekly. Buster Keaton may have risked life and limb a bit more on the set of 1926’s also-essential The General, but here Chaplin used comedy to take real political risks on the world stage.

11. Airplane! (1980)

A handful of films become so successful they birth entire sub-genres, and while Airplane! was certainly the offspring of any number of zany, cartoonish parents, there’s never been a brat like it, before or since. On the surface it’s a parody of the (then) trendy disaster-film craze of the ’70s, but anyone who has memorized its acrobatic dialogue and merciless pacing knows Jim Abrahams and the Zucker Brothers permanently upped the ante on puns and sight gags. The Farrelly Brothers may have tweaked the recipe by dialing up the raunch and treacly romantic subplots, and South Park‘s Trey Parker and Matt Stone have similarly leaned on surreal, out-of-nowhere visual gags mixed with unapologetic race, gender and religion taboos. But as a whirlwind of divine corniness that rips the stuffing out of everything around it, Airplane! remains uniquely devastating.

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