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50 Greatest Comedies of the 21st Century

From rom-coms to raunch-coms, ‘Anchorman’ to ‘Wet Hot American Summer’ – the funniest movies of the new millennium so far

50 greatest comedies

What’s so funny? If you’re talking about screen comedy in the 21st century, the answer is easy: bumbling manchildren, the more boorish and clueless and stuck in their stunted adolescence, the better. Talking foxes, Huey Lewis-loving serial killers, world-saving marionettes, foul-mouthed political fixers and boisterous bridesmaids – all great as well. German father-daughter duos and goofy stoners? Bring ’em on! Headbanging teachers and backstabbing bureaucrats? Yes, we’ll take them too.

Since the turn of the century, we’ve giggled at the poignant and the perverse, rom-coms and raunch-coms, new-and-improved takes on singular comic types and loose, highly improvised ensemble pieces that spread the spotlight around. Some of these movies have been gently witty, while others have displayed all of the subtlety of a dose of Sex Panther cologne. But they’ve all consistently cracked us up, in a near–two-decade span in which – let’s be honest – we’ve need a laugh or two. Or three. Or a dozen.

After a number of heated arguments and lots of name-calling and the occasional chaotic pie fight, we’ve narrowed down our choices for the greatest comedies of the 21st century. Culling this down to a mere 50 entries was a tough call – humor is a seriously subjective topic, and every one of our 19 writers weighing in had their own idea of what constitutes “hilarious.” But this list represents the best cross-section of screen comedy of our still young millennium, a collection that runs the gamut from droll to bladder-loosening. Given the high possibility of sidesplitting, you may wanna have a medical professional on hand. And don’t forget to stay classy, San Diego.

'Enough Said' (2013)

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50

‘Enough Said’ (2013)

At the start of Nicole
Holofcener’s savvy L.A. rom-com, harried masseuse Eva tells a slobby
divorcé named Albert that she’s tired of her dates expecting her to be  “funny.” But when you’re played by Julia Louis-Dreyfus, you get laughs
whether you want to or not. Enough Said tracks what
happens when Eva finds out that Albert (played by James Gandolfini, in
one of his last roles) is the ex-husband of her favorite client
(Catherine Keener). But it’s really about the lead character’s experiences as a
middle-aged woman, exhausted by the flirting-and-flattery phase of
being single, and now eager just to be with a man she can be ordinary
around – which ironically, is when she’s at her most hilarious. NM

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49

‘American Psycho’ (2000)

Yes, it looks more like a slasher flick than a yukfest, what with Wall Street
yuppie Patrick Bateman heartlessly dismembering his nearest and dearest. But Mary
Harron’s adaptation of Bret Easton Ellis’ novel – which, at the core of its
ripped-out heart, was a satire – is one of the sharpest splat-stick comedies in
recent history, mostly because of how over-the-top it is. Christian Bale’s disaffected apex predator grows homicidally
envious of his colleagues’ business cards. He offers a thoughtful critique of
Huey Lewis’ discography while wilding an axe. Everybody mistakes each other for
somebody else. And it offered a better one-liner for going on a killing spree
than anything a Batman supervillain could come up with: “I have to return
some videotapes.” KG

'Fantastic Mr. Fox' (2009)

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48

‘Fantastic Mr. Fox’ (2009)

So the quintessential Wes Anderson dysfunctional family film is … a stop-motion animation adaptation of a Roald Dahl children’s book?! The filmmaker and his cowriter Noah Baumbach are loose with the details but loyal to the author’s fiendish spirit, plopping the irrepressible dandy thief/eponymous patriarch (George Clooney) in between avenging farmers and a community of furry creatures weary of his exploits. Anderson’s deadpan humor has never been better served than by anthropomorphized animal puppet reaction shots while – typecasting at its best – Willem Dafoe plays a rat and Bill Murray’s a put-upon badger. As for Clooney, he delivers a note-perfect, shockingly ham-free comedic performance. What the cuss? EH     

'Harold and Kumar Go to White Castle' (2004)

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47

‘Harold and Kumar Go to White Castle’ (2004)

A stoner comedy about a couple of twentysomething buddies on a “quick” road trip to feed their munchies has no right to be this eccentric, progressive and consistently hysterical. Kal Penn and John Cho rode a cheetah into movie history (and let us see Doogie Howser in a whole new light) as two potheads in search of the perfect slider. But our generation’s version of Cheech and Chong aren’t just out to satisfy their wake-and-bake fast-food cravings – they learn that being young and dumb enough to devote this much passion to getting exactly what you want when you want it is something that fades if you don’t live for the moment. We should all be more like Harold and Kumar. BT

'I Heart Huckabees' (2004)

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46

‘I Heart Huckabees’ (2004)

Jason Schwartzman is the sensitive, lovesick environmentalist getting his life audited by existential detectives Lily Tomlin and Dustin Hoffman. Mark Wahlberg is a philosophically woke fireman, Jude Law is a sleazy department store executive with an identity crisis, Naomi Watts is his beautiful girlfriend/spokesmodel stuck in a behavioral loop and Isabelle Huppert is … the devil? Nihilism? We’re not sure. What matters is that all of these characters are essentially director David O. Russell himself, in this bizarrely hilarious, symbolic and surreal melodrama of American life that keeps going in circles. Don’t let his post-Fighter respectability fool you – this is the movie that probably most accurately depicts what it’s like to be inside the filmmaker’s head. BE

'Legally Blonde' (2001)

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45

‘Legally Blonde’ (2001)

Having just been dumped by her Harvard-bound boyfriend for being too Marilyn Monroe and not enough Jackie Kennedy, sorority president Elle Woods (Reese Witherspoon) proceeds to prove she can be both. Suddenly, this supposedly ditzy dame is acing her LSATs and recording a video essay for the Cambridge college’s law school in a sparkly pink bikini. Surprise, it works! Take that, Ivy League stuffed shirts! This is the movie in which Witherspoon bend-and-snapped into our hearts, and in a comedy full of laughs, the lawyer with a heart of gold (and a mane to match) gets the last one, defying teachers and classmates’ expectations to become a courtroom superstar – in the most Elle Woods way possible. KYK

'The World’s End' (2013)

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44

‘The World’s End’ (2013)

The set-up is delightfully promising: A group of once-close friends reunite to finish the epic 12-bar pub crawl they attempted as wild, bright-eyed teens. Needless to say, things don’t quite go as planned, and out comes director Edgar Wright’s fondness for the bluster and buffoonery of a very particular kind of Gen-X male. But then the movie soon becomes something quite different, as our heroes are confronted with a hellishly hilarious, gruesome Body Snatchers-type sci-fi scenario – and unlike so many other wild comedic genre twists, this one simultaneously leans into and explodes the idea of learning that things look different from the perspective of age. The Cornetto Trilogy was always about growing up, but The World’s End shows the awesome destructive power of refusing to do so – in ways both heroic and catastrophic. BE

'Jackass: The Movie' (2002)

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43

‘Jackass: The Movie’ (2002)

Want to see a bottle rocket shoot from someone’s ass? How about a topless man in bike shorts rolling around on hundreds of mouse traps? Or a dude attempt to snort high-grade, hot-as-hell wasabi sauce? Imagine the Marquis de Sade remixed by Bozo the Clown and you’ll see the baroque comic-book masochism of Jackass: The Movie, the first in a trilogy of big-screen releases that started life as MTV’s breakout reality show. Johnny Knoxville and his stunt-drunk band of self-flagellant bros pioneer joyously extreme pre-YouTube gags. (And we mean gags literally: along with the onscreen shit, piss, and blood, there’s just so, so, so much vomit – some of it re-ingested.) It’s both riotously gut-busting, even as you worry that these overgrown skate-punk knuckleheads may need punchcards for their local emergency rooms. SG

'Kung Fu Hustle' (2004)

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42

‘Kung Fu Hustle’ (2004)

Stephen Chow understands one thing about martial-arts movies that’s too often forgotten: They should be funKung Fu Hustle works so well because its director/cowriter/star knows – hell, embraces – that his story of a wannabe gangster in 1930s Shanghai is the kind of movie that needs to be constantly topping itself. So he does just that, making each action sequence – a physics-defying fight against dozens of dapper thugs, a stand-off with a warrior named “the Beast,” a man-versus-axes showdown – more pulse-pounding yet hysterically ridiculous than the one before. It’s both a wuxia epic and a parody of one at the same time. If Buster Keaton and Jackie Chan had a baby, that kid would grow up to make this movie. BT

'Hail, Caesar! (2016)

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41

‘Hail, Caesar! (2016)

A madcap comedy that doubles as an oddball morality play, the Coen brothers’ hooray-for-Hollywood hootenanny stars Josh Brolin as Eddie Mannix, a studio fixer in early Fifties Tinseltown dealing with dim actors (see: George Clooney’s sublimely ridiculous Baird Whitlock), pregnant stars, miscast cowboys, scheming communists and other threats to his studio employers — all while trying to decided whether or not to pack it in. It’s as silly as any film the Coens have made, but it’s also rich in behind-the-scenes detail and surprisingly reflective on its hero’s Catholic faith. Anyone showing up for over-the-top musical numbers won’t be disappointed, either. KP

'Force Majeure' (2014)

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40

‘Force Majeure’ (2014)

How funny is it to watch a grown man cry? If it’s a Swedish man who, in a moment of weakness and terror, abandons his wife and kids to die in an avalanche, the correct answer is: “very funny, very funny indeed.” Filmmaker Ruben Östlund’s alpha-dude-in-crisis movie was plenty relevant when it came out in 2014; nowadays, it feels almost prophetic, having anticipated the epidemic of masculine selfishness that seems to be running roughshod over the culture. In that sense, it’s as much a horror movie as it is a masterpiece of cringe comedy – and a reminder that those two genres aren’t always that far apart. KL

'Sideways' (2004)

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39

‘Sideways’ (2004)

Alexander Payne’s
oenophilic comedy has likely put a dent in merlot sales forever, but it’s aged
into a quaffable vintage, courtesy of Paul Giamatti’s performance as a
self-loathing wine connoisseur. As he and his soon-to-be-married friend (Thomas Haden Church)
venture to California wine country for a bachelor weekend, Sideways
develops a sharp buddy-movie dynamic between a pungent misanthrope and
a pleasure-seeking horndog. There’s sweetness at the film’s core, drawn
out in his boozy courtship of a fellow enthusiast (Virginia Madsen), but Payne
gets a buzz off Giamatti’s ornery belligerence, which at one point has him
lunging for the wine-tasting spittoon. ST

'Wet Hot American Summer' (2001)

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38

‘Wet Hot American Summer’ (2001)

Meet the only film on this (or any other) list in which a deranged Vietnam veteran played by Law & Order: SVU’s Christopher Meloni learns valuable life lessons from a talking can of vegetables that can suck its own dick. (“And I do it a lot.”) With a gaggle of alums from the influential sketch comedy group the State both in front of and behind the camera – and a cast of soon-to-be superstars including Bradley Cooper, Amy Poehler, Elizabeth Banks and Paul Rudd – this send-up of raunchy Reagan-era teen comedies has an anything-for-a-laugh approach that actually gets laughs every time. This one-time cult curiosity has since spawned two Netflix spinoff series … as well as a legendary DVD audio commentary track that just adds extra fart sounds. STC

'Knocked Up' (2007)

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37

‘Knocked Up’ (2007)

Filmmaker Judd Apatow’s chronicle of a one-night
stand gone horribly wrong would have worked perfectly fine as Farrelly
Brothers, gross-out comedy. But it’s the writer-director’s attention to detail that made
this a classic. In addition to watching Seth Rogen bumble around after getting
Katherine Heigl pregnant, Apatow included a horde of its schlubby hero’s screwball
friends, i.e. guys who fart on their buddy’s pillows to give each other pinkeye. And for all of the romcom’s relentless gags, it has a heartstring-tugging story arc that keeps you rooting
for Rogen’s natural underdog until the last scene. KG

'High Fidelity' (2000)

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36

‘High Fidelity’ (2000)

Stephen Frears’ adaptation of Nick
Hornby’s novel wryly tackles the culture of record-store gatekeepers, led by a stubbornly romantic John Cusack in the definitive Cusackian performance (all apologies, Lloyd Dobler). Aided by a manic breakout
performance by Jack Black, this comedy functions
as a gentle tribute to anal-retentive, list-making music snobs everywhere, even as it skewers the adolescent male dream of waiting for “the
perfect girl.” Watch out for a pitch-perfect Springsteen cameo and the ultimate rejoinder to anyone who demands taste
supremacy: “How can it be bullshit to state a preference?” VM

'Bad Santa' (2003)

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35

‘Bad Santa’ (2003)

Grinches never had a Christmas movie to call their own. And then Billy Bob Thornton slapped on a gin-soaked beard and a vomit-encrusted Santa suit, and tucked everyone’s stockings with the fattest piece of coal in the mine. What’s remarkable about Bad Santa is how far its director, Terry Zwigoff (Ghost World), goes to avoid any hint of Yuletide sentimentality: Thornton’s thieving Kris Kringle is a degenerate alcoholic who works malls, hates kids and loves anal sex with equal passion. Not to mention that the snot-nosed, Claus-crazy imp who’s supposed to redeem him, the unfortunately named Thurman Merman (Brett Kelly), is the rare outcast that’s genuinely disturbing. We are all John Ritter reaction shots. ST 

'Adaptation' (2002)

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34

‘Adaptation’ (2002)

An “adaptation” of New Yorker writer Susan Orlean’s book about a true life Floridian flower thief, one starring Oscar winners Meryl Streep and Nicolas Cage, doesn’t naturally suggest comedy … except for the fact that it was written by the era’s great meta-fictional gag man, Charlie Kaufman. The neurotic genius turned an ill-fitting gig into a hilariously self-incriminating vivisection of the movie business, with Cage playing both Charlie and his less scrupulous brother (fictional but credited as a co-writer, because of course), absolutely straight – and still getting laughs through fidelity to Kaufman’s rapid-fire self-owning. It proved that an aggressively smart, formally disorienting movie could still let everyone in on the joke. EH

'Ghost World' (2001)

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33

‘Ghost World’ (2001)

This just in: Precocious teens can be real assholes. Directed by Terry Zwigoff (Crumb), the film adaptation of Daniel Clowes’ comic cast Thora Birch in the career-defining role of smart, cruel young woman named Enid, who distracts herself with obscure music, afternoons at the diner and a flair for talking trash about hometown dorks with her best friend, Rebecca (Scarlett Johansson). It takes a middle-aged record geek (Steve Buscemi, going full-on Steve Buscemi) to crack Enid’s derisive shell – at which point this bittersweet comedy catalyzes her timeless realization that it’s easier to mock other people’s lives than to make one of your own. JBe

'The Lobster' (2015)

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32

‘The Lobster’ (2015)

Welcome to the darkest of dark comedies – a satire of romance in which the laughs all have serrated edges. Director Yorgos Lanthimos, who previously crafted the bleakly hilarious family drama Dogtooth, introduces us to a future society in which everyone must find a mate or be turned into an animal. Colin Farrell is magnificently deadpan as the newly dumped David who goes looking for love in all the wrong places. With The Lobster, Lanthimos doesn’t just poke fun at the grimness of dystopian dramas: He’s gleefully ridiculing a culture in which marriage is a convenient distraction from loneliness and true love is a lie you tell to trick someone into settling down. And it’s got the best EDM joke ever. TG

'The Royal Tenenbaums' (2001)

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31

‘The Royal Tenenbaums’ (2001)

Set in a storybook vision of New York drawn in equal parts from old New Yorker cartoons and Salinger’s Glass family stories, Wes Anderson’s sprawling third feature mines laughs and pathos from one family’s decades of pent-up resentment, disappointment and unexpressed desires. Gene Hackman plays the neglectful patriarch of a family that includes a resentful ex-wife (Anjelica Huston) and three children who never lived up to their early potential: a burnt-out athlete (Luke Wilson), a failed playwright (Gwyneth Paltrow) and a paranoid stockbroker (Ben Stiller). The director’s signature precise-to-precious filmmaking, clever dialogue and painstakingly designed world of board game closets, tracksuit-clad kids and wannabe cowboy authors keep it funny. The emotions roiling beneath its colorful surface keep it real. KP

'Hot Fuzz' (2007)

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30

‘Hot Fuzz’ (2007)

Mel Brooks once noted that parody plays best when it looks like the real thing – a lesson that director Edgar Wright has definitely taken to heart. Reteaming with frequent co-writer/star Simon Pegg and their partner-in-crime Nick Frost, the filmmaker and friends send up the conventions of the contemporary, “Bayhem”-infused cop action flick in this story of a maverick London detective reassigned to a provincial police force. There’s only the tiniest degree of separation – and silliness – between Hot Fuzz‘s big set pieces and those of Bad Boys 2 or Point Break (both of which are explicitly referenced). But in that sliver, the movie finds huge laughs and a delightful sense of small-town anarchy in the U.K. JBa

'Team America: World Police' (2004)

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29

‘Team America: World Police’ (2004)

Remember the halcyon days of 2004 when the United States didn’t yet realize 9/11 and our invasion of Iraq would trigger decade(s)-plus of escalating chaos? South Park creators Trey Parker and Matt Stone turn a goof on an old, semi-obscure Sixties kids’ show (Gerry Anderson’s Thunderbirds) into a take-no-prisoners puppet-apalooza, ripping into gung-ho military jingoists, foreign-policy hawks, limousine-liberal movie stars, broadway musicals and every single movie montage set to a patriotic country song. The fact that it has not dated at all but seems more timely than ever is, frankly, depressing and sad. But then you remember that it features puppets having the most pornographic sex imaginable. Amer-i-ca! Fuck yeah! AN 

'Superbad' (2007)

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28

‘Superbad’ (2007)

Taking a page out of their mentor Judd Apatow’s book, cowriters/BFFs Seth Rogen and Evan Goldberg went back to their youth and crafted a teen comedy with dick drawings (dozens of ’em), dirty jokes … and a heart and soul. Yes, it’s about two high-school dudes (Jonah Hill and Michael Cera) trying to get laid, and the antics involving a party gone out of bounds, period blood, a character named “McLovin’,” kooky cops and copious alcohol consumption that ensue – so far, so grossout. But underneath all the teen-boys-are-genuinely-disgusting humor and Porkys-style shenanigans is
a thread of deep-seated insecurity, stemming from the fact that
adulthood is fast approaching and soon these close friends will be heading off to different
colleges. By that time that talking about “p in vagee” gives way to an affectionate “boop” at the end, you’re smitten. All this, plus a near-perfect turn from Emma Stone. Super, indeed. EZ