The 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 Anchorman, Old 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.

10. The Jerk (1979)

Finding a more likable lead than Steve Martin would have been impossible for this fish-out-of-water tale, which was inspired by a single line in Martin’s standup act and traces Navin R. Johnson’s rise from a poor “black” child to a wealthy, accidental inventor – and back to the literal gutter again. Like Being There, the lead’s innocence and simplicity is contrasted to great effect with the cold, hard world around him. Palpable chemistry between Martin and Bernadette Peters elevates what could have been a casually sketched love story into something classic, dignified, and sweet. Martin is eager to please in his first starring role, never turning up his nose at a dumb bit of humor. That helps separate The Jerk from a lot of the tortured, gritty stuff around it. Like a silent movie (with bells and whistles) or a talkie that walks (and stumbles, and crashes to the ground), its core is the sparkle-eyed hopefulness of The American Optimist. However moronic.

9. Raising Arizona (1987)

Ranking this visual tour-de-force above the more nuanced, patient, and self-consciously epic The Big Lebowski is tough, since the latter shows everything the Coen Brothers learned in the decade that separates the two films. But it also reinforces how utterly accomplished Raising Arizona was from the start, its fractured take on the American Dream dripping with a heartbreaking and visceral realness. Nicholas Cage gives a cringe-inducing performance as a hopeful punching bag whose physical and psychic environment buzzes with constant threats, grand literary motifs, poopy diapers, and creepy, deluded friends and foes, and Holly Hunter emotionally dominates every scene she’s in. There’s not a line or glance that doesn’t achieve its full potential, and much like Lebowski, it manages to make suffocating stillness and kinetic explosions of action look like different limbs of the same smoke-stained, beer-swilling underdog.

8. This Is Spinal Tap (1984)

Before Best in Show, or the ballsy, genuine awkwardness of Borat, there was Spinal Tap, the film that launched dozens of catchphrases and a handful of brilliant careers. Rob Reiner’s instinct to dive headfirst into hard-rock clichés was spot-on, although watching it now it’s hard to believe this is the same guy who would later make When Harry Met Sally (a film that, to be fair, set its own stylistic templates but did so with far fewer laugh-out-loud moments). Spinal Tap is brilliant not because it’s universal, though you’d be hard-pressed to find a comedy or music aficionado who didn’t love it, but because it achieves perfection in the relatively tiny pond it sets out to drain. Creatively and as an industry, music has devoured and crapped itself out several times over since Spinal Tap came out, but this daddy of all mockumentaries reassures us there will always be a place for big bottoms, love pumps, and anything that goes to 11.

7. Caddyshack (1980)

You don’t need a black light to see the fingerprints of Caddyshack on countless contemporary ensemble comedies. But in choosing Caddyshack over its anarchic spiritual brethren, such as John Landis’s Animal House and Blues Brothers, or director Harold Ramis’ almost-as-stellar Vacation, one must acknowledge the unmatched zeal and affection it shows for freaks, misfits, and outcasts of all stripes. Pick any scene in the film and you’re likely to see an example of something Ramis and his cast and crew either invented or perfected in the realm of feature-length comedy. Perhaps it’s not surprising that lead writer Brian Doyle-Murray based it largely on real-life experiences, given how specific most of the situations feel. But it’s also a tour-de-force of improvisational filmmaking, as any Caddyshack buff can tell you, a loosely-scripted lark that evolved significantly as it was created. Chevy Chase, Bill Murray, and Rodney Dangerfield form the heart of the movie in all their gangly, immature glory, but it remains a loose, youthful, and living thing, as well as the quintessential late ‘70s/’80s comedy, because it began as one.

6. Annie Hall (1977)

Woody Allen’s New York is as lovingly rendered in Annie Hall as his Los Angeles is thin, vacuous, and disposable, which makes it all the more impressive how well he and Diane Keaton ground the film in a frustrated romantic reality. Fans of early Allen fantasies like Bananas and Sleeper could scarcely have predicted the level of autobiographical candor he brought to Annie Hall, which essentially set the beats and structure of the modern, dialogue-driven romantic comedy. Allen’s portrayal of the neurotic, existentially tortured comedian Alvy Singer bucks all assumptions about whether or not thoughtful, savagely clever films can make it at the box office – or become the rare comedy to win a Best Picture statuette. As with relationships in general, we willingly submit to its melancholy hazing from time to time because it reminds us how fragile, temporary, and thrilling life can be. The sorrow! The pity! The mantras!

5. Duck Soup (1933)

If it wasn’t already clear that the Marx Brothers were a team effort, their best film – the bonkers-by-any-standard Duck Soup –  was neither written nor directed by Groucho, Harpo, Chico, and Zeppo. That’s not uncommon for the time period, but it’s more proof that great performances can own a film. Amid contract disputes and uncertainty with Paramount Pictures, the brothers managed to turn a quasi-political farce about the invented country of Freedonia into the most consistent example of slapstick genius and vaudeville-indebted routines in film history. Never mind the embarrassment of purely visual riches, such as Harpo’s mirror scene, or Harper and Chico teaming up to drive a lemonade salesman nuts. The film’s subversive takes on sex and the evils (and idiocy) of war deepen the riotous physicality in a way that also-excellent Marx Brothers films like Animal Crackers, Horse Feathers, and A Night at the Opera never could.

4. Monty Python and the Holy Grail (1975)

Plenty of Python fans will fist-fight you over which sketch or character is their favorite (and therefore best), but there’s little question that Holy Grail is the British outfit’s most fiendishly inspired full-length outing. Like Life of Brian and The Meaning of Life, both of which came after Holy Grail, it’s chiefly concerned with slathering Python’s devastating wit and surreal ideas over implicitly Big-Picture topics like mortality, the innate dignity of the soul, political repression, and more. Unlike those films, it’s got an urgency born from its production particulars (having been conceived between seasons 3 and 4 of their TV series), a relatively paltry budget, and the fact that the Pythons successfully translated their fearless experimentation from television to the big screen. Like the Beatles bouncing dozens of tracks to preciously small amounts of 4-track tape, this Arthurian fable is densely packed with superb ideas executed flawlessly.

3. Some Like It Hot (1959)

Before Tootsie, Mrs. Doubtfire or The Birdcage, Some Like It Hot mined plenty of good-natured humor from the world of gender-bending, as the totally-game and beautifully paired Jack Lemmon and Tony Curtis proved when they donned dresses, wigs, and thick makeup to escape the mob, swiftly falling in with the already-famous bombshell Marilyn Monroe. Some Like It Hot rests near the top of director Billy Wilder’s intimidating list of cinematic triumphs largely because of its painstaking craft, which maximizes every angle, line of dialogue, and second of the viewer’s attention. Add to that three of the most iconic, magnetic, easygoing (on screen, anyway) personalities of 20th century Hollywood, a gorgeously black-and-white look that bucked the colorization trend of the late 1950s, and – oh yeah – crack comedic timing and genuinely outlandish situations, and you’re left with one of the most exuberant, endlessly watchable films in the English language.

2. Dr. Strangelove (Or How I Learned to Stop Worrying and Love the Bomb) (1964)

Stanley Kubrick’s black humor is evident in all his best work, but this Cold War masterpiece shows what happens when biting political satire rams headlong into a razor-sharp script (adapted from Peter George’s Red Alert, with his help) and arguably the most detail-oriented comedic acting in film history. Peter Sellers is (still) a scene-stealing revelation as multiple, equally ludicrous characters, particularly the film’s ex-Nazi namesake. Sterling Hayden’s General Ripper and his obsession with precious bodily fluids still rings true and loud on so many levels, as does the scathing commentary on global brinksmanship that could have been written last year instead of a half century ago. As provocative as it is symbolic, it’s one of the most visually and tonally influential comedies of all time because it works hard for each and every laugh it gets, and assumes nothing of the viewer except a brain and a sense of humor.

1. Blazing Saddles (1974)

It’s not that Blazing Saddles has a heart. If anything, the expert slapstick and loopy dialogue conceals a vicious hatred of charlatans and power-trippers of every type. Its red-hot branding iron reserves pity for no one. It’s that even when it’s their stated intention or ambition, most films fail to portray enduring truths about race, gender, tribalism, politics, friendship, and shotgun blasts of campfire flatulence with a tenth of the guts or glory of Mel Brooks’ best movie. Even calling it that is saying a lot, considering this is the guy who made The Producers and Young Frankenstein. But as every movie that’s been released since Blazing Saddles has proven, it’s not simply the quintessential Western comedy, or the quintessential comedy about America in all her contradictions, failings, and victories. It’s the quintessential filmed comedy because everything about it resonated on its first outing, and continues to resonate on each successive go-round. There’s stunning variety in the writing (courtesy of Brooks, Richard Pryor, Gene Wilder and others) and an almost otherworldly quality to the assured performances, a far-head-of-its-time prescience in the subject matter, and a vulgarity that sounds shocking anywhere, at any time. Maybe it’s because we’re still struggling with the same issues today as we were in 1974, or 1874. Maybe it’s because it’s a film about the very nature of films, a reckoning of the lies Westerns told us. It’s everything it can and should be. As Harvey Korman’s Hedley Lamarr says at one point, “My mind is a raging torrent, flooded with rivulets of thought cascading into a waterfall of creative alternatives.” To which Slim Pickens’ Taggart replies, “God darn it, Mr. Lamarr, you use your tongue prettier than a twenty dollar whore.”

The 20 Best Comedy Movies of All Time