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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)



‘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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‘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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‘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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‘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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‘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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‘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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‘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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‘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)



‘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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‘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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‘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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‘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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‘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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‘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)



‘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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‘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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‘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)



‘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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‘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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‘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)



‘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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‘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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‘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

'24 Hour Party People' (2002)

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’24 Hour Party People’ (2002)

Thanks to his signature character Alan Partridge, comedian Steve Coogan is an expert at playing a legend in his own mind. But what if the legend lived up to the hype? That’s the wild sex-drugs-and-rock & roll thrill behind this stranger-than-fiction true(ish) story of influential music-biz pioneer Tony Wilson – a blowhard TV-news cornball turned record-label founder and nightclub impresario who brought Joy Division, New Order and Happy Mondays to the world before going broke. Coogan and his frequent collaborator, director Michael Winterbottom, chronicle Wilson’s rise and fall with fourth-wall-breaking bravura and good-natured glee. STC

'Frances Ha' (2012)

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‘Frances Ha’ (2012)

Who likes understated, black-and-white slice-of-life dramedies that pop with colorful humor and awkward comments? Twentysomething angst doesn’t get any better or more comically bittersweet than this cracked character study from director Noah Baumbach and cowriter/star Great Gerwig, in which the eponymous heroine aimlessly pings from downtown Manhattan to Northern California, Paris to Vassar – yet really just ends up going endlessly in circles. There are plenty of slapstick comedy moments as Gerwig’s lost soul busts up old friendships and burn bridges, but this minor gem thrives on the laughter bred from cringe-worthy moments. “I’m embarrassed. I’m not a real person yet.” Neither are we, Frances. Neither are we. KYK

'School of Rock' (2003)

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‘School of Rock’ (2003)

There were always hints of
Jack Black’s potential greatness in the acoustic-metal grandiosity of Tenacious
D and the record-clerk pomposity of High Fidelity – but it took Richard
Linklater to get a full-service performance out of him. The comedian’s passion for the
guitar gods of yesteryear made him the only choice to play a would-be rocker
who fakes his way into a fifth-grade substitute teaching gig and turns his
musically gifted students into his backing band. The jam sessions and “rock
appreciation and theory” classes find Black perfectly in his element,
but little touches make the difference, too: His poor, rumpled approximation of
what a teacher is supposed to sound like; his little shimmy toward Joan Cusack
to Stevie Nicks’ “Edge of Seventeen”: and his tender treatment of a young
singer with stage fright. Play this comedy loud. ST

'Love & Friendship' (2016)



‘Love & Friendship’ (2016)

In his Nineties indie classics Metropolitan and The Last Days of Disco, Whit Stillman told witty tales of cultured New Yorkers,
obsessed with social codes adopted from Jane Austen novels. Given the
chance to adapt Austen’s actual work, the writer-director unexpectedly embraced one
of author’s most unapologetically amoral characters: the
social-climbing widow Lady Susan, from the novella of the same name.
Kate Beckinsale is an absolute delight as the anti-heroine, who
conspires with her equally shameless American pal (Chloë Sevigny) to
manipulate the super-rich, including a moneyed doofus well-played by Tom
Bennett. Throughout Love & Friendship, Susan amusingly weaponizes upper-class politeness, exploiting her hosts’ fear of rudeness to milk them for all they’ve got. NM

'The Trip' (2010)

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‘The Trip’ (2010)

In which British comedians and longtime buds/collaborators Steve Coogan and Rob Brydon drive through the English countryside, sampling food and wine that costs more than your monthly rent and turning dueling Michael Caine impersonations into a game of showbiz oneupmanship. The first in a series of comic travelogues that the duo did for the BBC and turned into feature-length free-for-all goofs, it’s a road movie that enjoys taking the piss out of male insecurities and showbiz narcissism almost as much as providing a showcase for its stars’ particular gifts. It’s the comedic My Dinner With Andre that you never knew you were waiting for. KL

'The LEGO Movie' (2014)

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‘The LEGO Movie’ (2014)

Forget the Solo debacle: No two filmmakers are better at skewering the whiz-bang sugar rush of blockbuster cinema than Phil Lord and Chris Miller. The geniuses behind the Jump Street films transformed what could have been a toy ad into a subversive, thrilling action-comedy that celebrated the power of make-believe while mocking the conformity of corporate culture. Chris Pratt voiced the sweet, enthusiastic Emmet, who learns that he’s “the one” who alone can save the universe – a clichéd movie trope that, like many other tentpole tenets, Lord and Miller have a ball spoofing. Equally hilarious and heartfelt, The Lego Movie is a tsunami of sight gags, pop-culture ribbing and killer zingers. It imagines a universe where Superman desperately wants to get away from the super-needy Green Lantern; where the love interest goes by Wyldstyle but really doesn’t want you thinking she’s a DJ; and where Batman is the biggest douche on the block. Everything is awesome! TG

'Borat: Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan' (2006)

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‘Borat: Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan’ (2006)

Was Sacha Baron Cohen exploiting his unsuspecting marks – be they big city feminists, bigoted rodeo audiences, psycho gun merchants, unsuspecting news anchors or craven politicians – by pretending to be a dimwitted, bigoted Kazakh journalist on a journey through America? Was he being unfair to the people of Kazakhstan? Is it against the law to take a dump in front of Trump Tower? Should people refrain from ever saying “my wife” in that accent? All of these things may be true, and yet Borat has lost none of its punch as a laugh machine, in part because the humor often come from deeply uncomfortable places. Indeed, it sometimes feels like the film both captured and embodied something rotten in the American soul at a critical point. Yes, this movie becomes harder to watch as the years pass by. And yet, somehow, it also becomes funnier. BE

'The Grand Budapest Hotel' (2014)

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‘The Grand Budapest Hotel’ (2014)

Wes Anderson drops his patented doll-house stylistics and deep-cut quirk into Mitteleuropa on the eve of World War II, as various folks pass through a lavish luxury hotel run by one Gustave H. (Ralph Fiennes) – a buffoonish dandy, “ruthless adventurer and a con artist, who prays on feeble-minded, sick old ladies” and realizes, too late, that his worldview is on a collision course with history. There’s the usual stable of Anderson rep company players (Bill Murray, Tilda Swinton, Willem Dafoe, Edward Norton), a mentor/student relationship involving a bellboy named Moustafa (Tony Revolori) and absurd side plots involving invaluable paintings and prison breaks. But what really makes this comedy work is the Fiennes madness at its center; done in between Voldemort duties and other villainous roles, his living relic of a bygone age is one of the greatest comic creations of recent years, elevating the
movie beyond the meticulous charm the filmmaker naturally delivers. “I go to bed with all of my friends.” EZ

'Mean Girls' (2004)

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‘Mean Girls’ (2004)

It’s high school as hierarchical hell, a world full of J.V. jocks and girls who eat their feelings, desperate wannabes and burnouts – and the Plastics, led by Queen Bee Regina George. Tina Fey established herself as one of America’s best comedy writers courtesy of this instant teen-movie classic, which boasts one of the most quotable scripts of the past 20 years (“Stop trying to make ‘fetch’ happen”; “Boo you whore”; “On Wednesdays we wear pink”; “If you’re from Africa, why are you white?”) and will forever endear Lindsay Lohan to us no matter what. While the portrayal of popularity borderline satirical, the laughter comes with a bit of a sting – it’s a peerless reminder of how funny and how shitty your teen years were. KYK

'Tropic Thunder' (2008)

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‘Tropic Thunder’ (2008)

Ben Stiller’s 2008 Hollywood burlesque is so spot-on, he even gets the right studio logos for the opening’s fake trailers. (Why yes, the indie tortured gay-monk drama would be a Fox Searchlight release.) A film’s cast and crew is stranded in the jungle when an Apocalypse Now-style war movie runs awry – at which point this satire mercilessly punctures the egotism, marketing and jargon of movie stardom, with plenty of residual bile for the cogs of the studio machine. The ensemble cast is a who’s who of comic firepower, with Robert Downey Jr. as a ridiculously extreme Method actor and Tom Cruise (nearly unrecognizable under pounds of make-up and a bald cap) as a crass, loathsome executive both vying for MVP status. JBa

'What We Do in the Shadows' (2014)



‘What We Do in the Shadows’ (2014)

Taika Waititi and Jemaine Clement’s macabre mock doc about vampires is great PR for creatures of the night and the perfect introduction to New Zealand’s deader-than-deadpan humor – a wonderfully inane strain that thinks nothing of blending gory set pieces with po-faced reaction shots to the camera and plenty of stealth quotables. (“We’re werewolves, not swear-wolves.”) As this houseful of bloodsuckers bickers, blusters and try not to wake up an 8,000-year-old roommate, the filmmakers keep mining every nook and cranny of his premise for laughs, and with a $1.6 million budget, this comedy squeezes in more jokes-per-dollar than every other film on the list. You can see why Marvel felt confident in letting Waititi wreak humorous havoc with a Thor-in-outer-space movie. AN 

'Lady Bird' (2017)



‘Lady Bird’ (2017)

It’s easy to make a high school movie that’s funny; it’s
significantly trickier to make one that also feels true. Greta Gerwig’s solo directorial debut doesn’t get
its laughs from outsize gags or teens spewing dialogue so clever that it
could only have been written by a 45-year-old. In fact, the Sacramento Catholic high school
circa 2002 where Christine “Lady Bird” McPherson
(Saoirse Ronan) matriculates seems so real that you can practically
smell the acne cream – and therein lies the humor. Everything our heroine experiences in her senior
year – from a bizarre teen Sondheim production to mother-daughter dress
shopping to dumb crushes and disappointing sex – cracks us up in only the way that something like a memory can. JS

'A Serious Man' (2009)

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‘A Serious Man’ (2009)

Joel and Ethan Coen make their most personal film yet, a unsettlingly uproarious Job parable set in their Minnesota hometown of St. Louis Park and its tight Jewish community. A put-upon physics professor up for tenure watches his marriage falls apart, while his cyst-suffering, Mentaculus-obsessed brother is wanted by the police and his reefer-loving son preps for an upcoming Bar Mitzvah. But the real subject is an unjust universe, where Heisenberg’s uncertainty principle and Schrödinger’s cat only deepen the mystery of a life rife with obtuse rabbis, fuzzy F-Troop reception and dogged calls from the Columbia Record Club. A Rosetta Stone for deciphering the filmmakers’ signature brand of empathetic nihilism and its place in the Judaic storytelling tradition, A Serious Man mixes cringe-worthy comedy with caustic insights about the struggle for meaning in a naggingly enigmatic world. SG

'Everybody Wants Some!!' (2016)

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‘Everybody Wants Some!!’ (2016)

For this “spiritual sequel” to his spirit-of-’76 classic Dazed and Confused, Richard Linklater captured another turning-point moment in the lives of some young Texans. Instead of the last day of high school in our nation’s bicentennial year, we ride shotgun with some baseball players during the first weekend of college circa 1980. Over a drunken stretch of days, a group of jocks and other early arrivals play scarily aggressive games of ping pong, attempt stoned telepathy, share favorite Twilight Zone episodes, line dance, slam dance and otherwise get to know each other while trying to figure out who they’ll be for the next four years. It’s rowdy fun even as Linklater keeps offering reminders that the good times won’t last forever. KP 

'The Death of Stalin' (2017)

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‘The Death of Stalin’ (2017)

It’s a hilariously corrosive concept: Oddballs like Steve Buscemi, Simon Russell Beale, Jeffrey Tambor and Michael Palin act out the politburo power
struggle that emerged in the wake of Joseph Stalin’s demise in 1953, practically tripping over the corpse to ensure a seat at the head of table. Sure, it sounds like an episode of Drunk History, but writer-director Armando Iannucci
manages to craft spit-worthy dialogue while making it very clear that lives are
at risk. Some of the material is innately ridiculous – Stalin’s
deadbeat son (Rupert Friend) berating a hockey team, for instance – but it’s
where the comedy of errors gets brutal that the satire truly earns its bones. To quote Buscemi’s Nikita Khrushchev: You laugh so you don’t get shot. EZ




‘Anchorman’ (2004)

Two years removed from his triumphant Saturday Night Live run, Will Ferrell
cemented his transition to movie stardom (already in full swing thanks to Old School and Elf) with this masterstroke of absurdist, blowhard comedy. In Ron
Burgundy, Ferrell and his frequent collaborator/director/co-writer Adam
McKay found the perfect delivery device for the actor’s hilarious sendup of
alpha-male privilege, playing the buffoonish, sexist San Diego newscaster whose
cocksure reign is about to be punctured. It helped also established Ferrell’s brilliant non-sequitur oddness: How a bull session about
love segues inexplicably into an impromptu a
cappella performance of “Afternoon Delight,
” or how a rivalry with other news crews effortlessly turns into a Warriors-style street brawl. And it’s quotable as hell, from Burgundy’s declaration that San Diego is German for “a whale’s vagina” to his insistence that he’s “in a glass case of emotion.” In the not-too-distant future, we’ll all be speaking in Burgundy-isms. TG

'In Bruges'

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‘In Bruges’ (2008)

“Maybe that’s what Hell is: the entire rest of eternity spent in Bruges.” So says Colin Farrell in Martin McDonagh’s feature-length debut, which is to so-called “dark” comedies what a black hole is to turning off your bedside lamp. The award-winning playwright-turned-filmmaker manages to extract humor from such noted comedic touchstones as accidentally killing a child, Belgian tourist destinations and Ralph Fiennes in a frothing rage – and infuses it all with the deft, distinct sense of morality he had polished over his years with his stage work. And whether you loved or hated Three Billboards Outside Ebbing, Missouri, it’s hard not to pine for the days when McDonagh’s dialogue was being read in Irish accents, particularly when one of those accents belongs to Brendan Gleeson. KL

'State and Main' (2000)

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‘State and Main’ (2000)

Writer-director David Mamet’s spirited showbiz satire skewers Hollywood pretension, casting a pre-30 Rock Alec Baldwin as a vain, lecherous movie star who gets into trouble when his latest over-budget production rolls into a sleepy Vermont small town. A crude, pushy director (William H. Macy), a sad-sack screenwriter (Philip Seymour Hoffman), and an emotionally fragile leading lady (Sarah Jessica Parker) take turns getting fleeced by not-as-innocent-as-they-look locals, as Mamet makes his version of a fast-paced backstage farce. State and Main is both savage and silly, a genius riff on the chutzpah of the rich and famous filled with hep, imaginatively vulgar lines: “Who designed these costumes? It looks like Edith Head puked, and that puke designed these costumes.” NM

'The 40 Year Old Virgin' (2004)

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‘The 40 Year Old Virgin’ (2005)

Judd Apatow had already made a name for himself with small-screen sketch comedy (he co-created The Ben Stiller Show), peerless cringe-comedy (The Larry Sander Show) and sensitive character-based comedy (R.I.P., Freaks and Geeks). For his big-screen directorial debut, he took a bit from all three and concocted what’s become a modern-comic urtext: the heavily improvised, ensemble-cast manchild farce. A post-Daily Show/pre-The Office Steve Carell is the title character, a geek-culture lifer who’s never had a real relationship; a crack team of supporting players including Romany Malco, Jane Lynch, Seth Rogen and Paul Rudd offer horrible romantic advice and off-the-cuff riffs about everything from soft rock to skin-mag stashes. (Seen today, the Rudd/Rogen volley of absurd “you’re gay” playground taunts is somehow both a highlight and a low point.) The talent bench is deep here – blink and you’ll miss Kat Dennings, Mindy Kaling, Jonah Hill and Kevin Hart in small parts – while Apatow’s knack for connecting outrageous set pieces with a surprisingly overall sweetness would become his signature. But it starts here, and as everyone knows, you never forget your first time. DF

'Shaun of the Dead'

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‘Shaun of the Dead’ (2004)

Best spoof of the century? Director Edgar Wright’s breakthrough film takes the piss out of horror movies, zombie flicks and post-apocalyptic dramas – and then, because he’s such a clever lad, still delivers a pretty riveting mash-up of those styles on top of it. Shaun of the Dead is really funny and really frightening, with each tone enhancing the other; co-writer Simon Pegg’s ordinary bloke is so bored by modern life that he doesn’t initially realize that the walking dead have invaded his town. You can see the early stages of the cheeky, stylish irreverence that would become the British filmmaker’s trademark, as well as generating tons of laughs from the dim-bulb rapport of Pegg and Nick Frost’s clueless characters. It’s so hilarious, in fact, that it takes a moment to realize how weirdly emotional it can be, too. The end of the world – somehow sidesplitting and touching. TG

'Toni Erdmann'

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‘Toni Erdmann’ (2016)

Unlikely as it may seem, one of the greatest comedies of the last two decades is a 162-minute movie from Germany. Writer-director Maren Ade spends most of that runtime testing the fragile bond between the two leads: corporate drone Ines Conradi (Sandra Hüller) and her incorrigible-prankster dad, Winifred (Peter Simonischek), who follows her on a business trip to Bucharest. When they inevitably fall out, he puts on a bad wig and re-enters her life as a boorish life coach named Toni Erdmann. Awkward exchanges, sweet father-daughter bonding and scenes that suggest serious undertones of feminist workplace frustration follow. The ending is legitimately profound, but Ade doesn’t just traffic in droll European humor. The triple whammy of karaoke, comic nudity and costumed lunacy that dominate the final hour is on par with anything in the Apatow universe. JBe

'Punch Drunk Love'

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‘Punch Drunk Love’

What did Paul Thomas Anderson see in Adam Sandler that nobody else had when he cast him as a lonely Los Angeleno? The answer: A rage that was never far from the surface of the comedian’s manchild characters. The filmmaker teases Sandler’s sound and fury out via a love story in which San Fernando Valley businessman Barry Egan falls for Lena (Emily Watson), a friend of one of his many sisters. They’re two misfit people who clearly belong together, even if his habit of bottling his ire until it explodes threatens both their relationship and the bathrooms of local restaurants. Also, did we mention the Provo, Utah phone-sex operators and Philip Seymour Hoffman’s vengeful mattress king? The film served as a kind of coming out for Anderson, who shook off the influences of his first films to get looser, stranger, more heartfelt and way funnier than he’d ever dared be before. KP


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‘Idiocracy’ (2006)

It took approximately six million years for humans to evolve from their apelike ancestors, but only about a decade for them to devolve more or less as Mike Judge’s satire predicted. Idiocracy takes place 500 years into the future, when colossal dumbasses have their lard-greased paws on all the levers of power and farms are irrigated by a popular sports drink. (“Brawndo: It’s What Plants Crave!”) Fox left the film for dead in theaters – it had no trailer, didn’t screen for critics and made less than half a million at the box office – but now it’s the go-to comedy of the Trump Era, a fun place to laugh about the dystopic trash pile that currently engulfs us. (If the current Secretary of Agriculture starting pumping Gatorade in fields throughout the Heartland, would he even lose his job?) ST

'Step Brothers'



‘Step Brothers’ (2008)

Will Ferrell is at his funniest when he’s got a
tag-team partner (see: AnchormanThe Other Guys) – but Step Brothers is, hands down, his best double act. Working alongside Talladega Nights chum
John C. Reilly, the duo play stunted adults forced into the same family when
their single parents (Richard Jenkins, Mary Steenburgen) remarry. They’re are the extreme edge of the bozo manchildren that made Ferrell a superstar and Reilly his goofball screen soul mate – it’s their back-and-forth idiocy that makes this a modern classic. And once
you’ve fully absorbed the brilliance of their interplay, be sure to spend
a little time marveling at the movie’s murderers’ row of ensemble players, including a perfectly repugnant Adam Scott and Kathryn Hahn as a horribly horny
wife. You’ll never hear “Sweet Child o’ Mine” the same way again. TG


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‘Bridesmaids’ (2011)

Champagne and cupcakes and party favor puppies wrapped up with string – Kristen Wiig throwing tantrums is our favorite thing. Decades from now, it’ll be clear that this story about a thirtysomething stuck in a rut and her fellow bridesmaids (the XX-chromosome counterparts to Judd Apatow’s stable of male kooks and losers) was a magic bean sprouting the future of studio comedies. Fresh faces like Rebel Wilson, Ellie Kemper, Chris O’Dowd and shock Oscar nominee Melissa McCarthy get plenty of room to make an impact; Wiig, fellow SNL vet Maya Rudolph and sly comic MVP Rose Byrne prove they’re superstar material. Proudly feminine and patently successful, this ensemble raunch-com celebrates the inner paranoia and outer politeness of best frenemies, all hugs with fingernails filed to a shiv. (And the there’s the instantly classic food-poisoning scene – who didn’t snort so hard their popcorn went flying?) Every studio wanted to copy it. None of them dared, which gave director Paul Feig years to dominate the no-fuck’s-given female blockbuster lane. Thanks to the seed Bridesmaids planted, now that turf is more crowded. AN

'In The Loop'

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‘In The Loop’ (2009)

Armando Ianucci’s bitter, foul-mouthed political satire about the Byzantine backroom back-and-forth between the U.S. and the U.K. in the run-up to a new war had a bitter ring of truth about it when it was released: The conflicts in both Iraq and Afghanistan were raging; the Bush administration was sword-rattling about Iran; and the future Veep creator’s distressingly plausible comedy demonstrated how terrible decisions could be made through a combination of ineptitude, spite and cover-your-ass cowardice. (The writer-director did his homework for this movie; he even famously broke into the U.S. State Department for research, which may have prompted new security protocols.) Seen now, this portrait of bureaucracy and institutional loyalty seems almost quaint – and yet, somewhere in there, amid the madness and nonstop motormouthed insults, Ianucci also gets at a powerful, prophetic truth: That in a world of rampant spinelessness, the cruelest man is king. BE

'Best in Show' (2000)

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‘Best in Show’ (2000)

The greatest comedy of the 21st century directly descended from one of the best of the 20th. Some 16 years after co-writing and starring in This Is Spinal Tap, Christopher Guest made this other milestone mockumentary – a flawless and deliriously executed work that transforms spoofery into something sublime. From Eugene Levy’s buck-toothed, two-left footed cuckold to Jane Lynch’s super-competitive trainer, every caricature miraculously becomes a sympathetic character, one deadpan line at a time. On the way to a competitive dog show, canines play straight men while their handlers run amuck. And then, halfway to the end, Fred Willard shows up and steals the show as a borscht belt TV commentator, delivering hoary one-liners so rapidly that you can barely catch your breath. No matter how ridiculous it all was, you walk away from Best in Show feeling that you’ve spent 90 minutes watching real people – and that comedy can carry the weight of our truly absurd lives. EH     

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