The 50 best comedies since 2000

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The 50 best comedies since 2000

Clockwise from left: Wet Hot American Summer’s Beth, Derek Zoolander, Bridesmaids’ Annie , Kung Fu Hustle’s Chow, The Grand Budapest Hotel’s Zero, Josie And The Pussycats’ Josie, and O Brother, Where Art Thou’s Everett (Illustration: Nick Wanserski)
Clockwise from left: Wet Hot American Summer’s Beth, Derek Zoolander, Bridesmaids’ Annie , Kung Fu Hustle’s Chow, The Grand Budapest Hotel’s Zero, Josie And The Pussycats’ Josie, and O Brother, Where Art Thou’s Everett (Illustration: Nick Wanserski)

Sixteen years in, our new millennium looks like a banner age for big-screen comedy, as eclectic as any that came before it. This is when Will Ferrell transformed the multiplex into a deliriously Dadaist screaming match; when Edgar Wright and David Wain perfected the art of the spoof, even as the Epic Movie crowd worked to destroy it; when the mockumentary came of age, with a big push from a Spinal Tap alum; and when comedians like Tina Fey and Melissa McCarthy crashed the boys’ club of mainstream comedy, the latter with an assist from Paul Feig, whose Ghostbusters reboot finally hits theaters this Friday. And that’s to say nothing of the big laughs major filmmakers like Wes Anderson, Paul Thomas Anderson, Roy Andersson, and several others with entirely different names smuggled into art houses over the past decade and a half.

When The A.V. Club decided to count down its favorite comedies since the turn of the century, polling a couple dozen of our staffers and contributors, some ground rules had to be established. For one, eligible films could mix genres, but they had to be predominately laugh-driven, which means that quite a few dramedies (Her, Lost In Translation) and horror-comedies (The Cabin In The Woods) were ruled out immediately. Secondly, and perhaps most importantly, we wouldn’t be ranking the funniest films since 2000. Comedy is subjective, and what makes one person chuckle may leave another stone-faced. Pure laugh count is an unreliable barometer of whether a comedy—a very flexible genre, as evidenced by the sheer variety of movies listed below—is worth your time. Did we miss anything essential? Make the joke on us and correct our oversights in the comments below.

50. Four Lions (2010)

Even for a writer and director who once devoted a half-hour comedy special to pedophilia (or at least the media hysteria surrounding it), an “Islamic suicide bomber comedy” might be something of a hard sell. But given the bleakness of its premise, Chris Morris’ 2010 feature directorial debut pulls an unexpected trick: empathy. Morris never ignores the fact that his characters—five bumbling, would-be suicide bombers with a tendency to compare paradise to the rides at a low-rent British amusement park—are idiots, plotting a dumb and evil thing. But he also never forgets that they’re human beings—especially Omar (Nightcrawler’s Riz Ahmed), the group’s sarcastic, morally conflicted leader, or Waj (Kayvan Novak), a big-hearted, smiling oaf whose poorly informed devotion to the cause provides Morris’ movie with its biggest laughs, and also its most devastating indictments of mindless and unthinking belief. [William Hughes]

49. Songs From The Second Floor (2000)

After writing and directing a couple of modest Swedish art films in the early ’70s, Roy Andersson spent the next two decades making award-winning commercials and shorts, before emerging into the world cinema scene seemingly out of nowhere with this visionary comedic nightmare. A masterful mix of Bergman, Fellini, Tati, and Monty Python, Songs From The Second Floor assembles a string of surreal, loosely connected sketches, mostly filmed in long takes on massive sets. The movie doesn’t tell a story so much as create an entire world on screen—one where ordinary folks see their jobs and culture sliding into an unexplained chaos. The gags in Songs are bleak, but masterfully delivered, in elaborately choreographed scenes that require viewers to scan the frame diligently, to catch every hilariously soul-crushing detail. [Noel Murray]

48. Josie And The Pussycats (2001)

Josie And The Pussycats might be the best movie John Waters never made. It takes the camp factor and cranks it up well past 11, likely somewhere into the 70s. But there’s no gross-out humor or Pink Flamingos-style “scare the squares.” No, instead the film pushes cheese through the looking glass, taking the story—pulled from an old Hanna-Barbera cartoon, itself based on an Archie comic—of three small-town girls nudged into the spotlight, then makes it so over the top, it goes beyond goofball into genuinely daring. It’s so littered with product placement, you start to suspect it’s actually a commercial, until you notice just how intentionally bonkers all the commodity-hawking is, and it becomes deliciously subversive. Josie And The Pussycats is an ideal party movie and a great piece of theoretical agitprop. Plus, it’s chock-full of catchy-as-hell songs. [Alex McCown]

47. Force Majeure (2014)

It’s really easy to say that you’d do the noble thing in a high-pressure situation. But sometimes the avalanche is roaring down the hill and all your brain tells you to do is grab your cell phone and book it. Who could blame a bourgeois young father for that? As it turns out, the wife and children he left to fend for themselves sure could. One moment’s cowardice sets off a chain reaction that destabilizes a family and dynamites its patriarch’s fragile masculinity, as merciless Swede Ruben Östlund points and laughs from behind the camera. Absurd machismo is a lethal punch line all on its own, and it gets better every time Östlund tells it. Add in a hilariously foreboding score, strong visuals, and the most pathetic rave scene of the new millennium, and we’re entering masterpiece territory. [Charles Bramesco]

46. Bad Santa (2003)

The holidays are a time for getting together with family, downing too much eggnog, and enjoying Bad Santa, the 2003 Yuletide comedy for the deviant in us all. Terry Zwigoff’s filthy masterpiece features the finest performance ever by Billy Bob Thornton, who stars as Willie T. Stokes, a drunken degenerate criminal who spends his winters working as a department store Santa Claus, all in order to rob his employers blind. That annual ritual is complicated by the antisocial cretin’s unlikely friendship with snot-nosed kid Thurman Merman (Brett Kelly), as well as by the suspicions of a mall manager (the late John Ritter) and security official (the late Bernie Mac). From alleyway vomiting to bouts of dressing-room anal sex to a bloody, wood-carved pickle given as a Christmas gift, Zwigoff’s film—whether in its original, unrated, or director’s cut—is almost unparalleled in its delivery of non-stop riotous inappropriateness. [Nick Schager]

45. 12:08 East Of Bucharest (2006)

To the pantheon of great comedy sequences set in television stations—think Albert Brooks’ anchor-desk meltdown in Broadcast News, or “Go fuck yourself, San Diego,” in Anchorman—we can add the second half of a tiny Romanian movie released in 2006. Invited to a panel discussion to share their reflections on the 16th anniversary of the fall of Ceausescu, three putative former revolutionaries end up out of their comfort zone and at each others’ throats about the details of what they did or didn’t do on the night in question. First-time director Corneliu Porumboiu casts his actors brilliantly and shows a prodigious command of screen space, emphasizing the amateurish camerawork of the local news crew to the point that every tilt and pan plays like a punch line. A study in drabness made with lively comic intelligence, as well as a deceptively featherweight meditation on heavy themes—e.g., what the individual can do against the machinery of totalitarianism—12:08 East Of Bucharest is worth seeking out immediately. [Adam Nayman]

44. The Color Wheel (2011)

“I don’t pinky swear, you know that. It’s a barbaric practice.” So declares Colin, a world-class misanthrope splitting the difference between Ignatius J. Reilly and a dropout from Kicking And Screaming’s graduating class. He’s come to help his sister J.R. move out of her ex-boyfriend/former professor’s place, and when their powers combine, they’re practically the Wonder Twins of bad vibes. Every page of script from stars Alex Ross Perry and Carlen Altman contains between four and seven immortal one-liners, viciously and deliciously cutting down everyone in the siblings’ direct vicinity, and more often than not, themselves. Realized in the gorgeous grain of monochrome 16mm film, this lo-fi screwball comedy isn’t just relentlessly funny. It’s also astute about the miniature frustrations of the post-graduate years, and better still, aware of how tiresome the sorts of people whining about such things really are. [Charles Bramesco]

43. State And Main (2000)

“Does it have to be an old mill?” a director (William H. Macy) asks a screenwriter (Philip Seymour Hoffman) of the key location in State And Main’s film within the film; only after considerable argument is it revealed that the project’s title is The Old Mill. David Mamet’s zinger-filled tale of a sleepy New England hamlet turned upside down by the arrival of a movie crew comes marvelously close to achieving the giddily cynical screwball rhythm of Preston Sturges classics like Hail The Conquering Hero and The Palm Beach Story, even as it retains the distinctive cadence of Mamet’s celebrated dialogue. (“Waterford, Vermont,” Macy tells someone when he’s asked where the shoot will be happening. “Where is it? It’s—that’s where it is.”) The superb ensemble cast—which also includes Alec Baldwin, Sarah Jessica Parker, Julia Stiles, David Paymer, and Clark Gregg—makes a fast-paced meal of the many one-liners they’ve been gifted. Mamet has since taken a hard turn into right-wing lunacy, so it’s unlikely that he’ll ever write anything so lighthearted again. Savor this one. [Mike D’Angelo]

42. Knocked Up (2007)

“An instant classic,” is how The New York Times’ A.O. Scott greeted the arrival of Judd Apatow’s unplanned-pregnancy comedy, and watching it nine years later, it’s not hard to see why. This is where Apatow’s early joke-a-minute instincts merged with his maturing sense of Albert Brooks-like emotional drama, fusing brilliant wit with heavy themes of adulthood and responsibility—specifically, the challenges of marriage and (cue Jonah Hill joke) child-rearing. Sure, the gender politics look a little dated, but so do Some Like It Hot’s. And Apatow again proves himself a master of capturing improvisational and unguarded moments, both hilarious and relatable. Plus, it still has the best mushroom-trip-in-Vegas ever put on tape. [Alex McCown]

41. Ocean’s Eleven (2001)

If Steven Soderbergh is our premier tycoon of cinematic cool, Ocean’s Eleven is his MGM Grand—a towering monument to the director’s sleek craft, his ease with performers, and his ability to move fluidly from the DIY fringes to the epicenter of Hollywood glamour. Also, it’s pretty damn funny. Rebooting a mostly forgotten Rat Pack vehicle, Soderbergh assembles Clooney, Pitt, Damon, Roberts, and a murderers’ row of character actors, then assigns most of them a role in an impossible caper: the plundering of an impregnable Vegas vault. As a heist movie, it’s blissfully tricky, doubling back on itself constantly. As an exercise in style, it keeps giving and giving, Soderbergh employing split screens and freeze frames to match the effortless panache of his characters. The real score: a barrel of laughs, and the rare modern blockbuster that feels light on its feet, not heavy as a plummeting asteroid. [A.A. Dowd]

40. Zoolander (2001)

Zoolander the movie is an awful lot like its titular male model: stupid to a fault, but also endearing and charming despite itself. Ben Stiller, who both directs and stars, understands the exact amount of effort to exert on a story about models brainwashed as assassins for a shadowy cabal of clothing manufacturers. Too much would strain the premise past breaking; too little would be a bore. The film succeeds on easy-going affability that occasionally—as with a playful gasoline fight—reaches the inspired. It also benefits from a worthy villain in Will Ferrell’s high-strung Mugatu, whose manic, quivering exasperation is partially fueled by being so aware of the absurdity of the world he inhabits. Zoolander is more jersey cotton than couture, and more comfortable for it. [Nick Wanserski]

39. Offside (2006)

The women in Jafar Panahi’s Offside are used to having it tough: They don slapdash male disguises and pay inflated ticket prices to get into an Iranian soccer game, only to be busted and penned just outside the stadium, agonizingly close to the action. But though political frustration drives the movie—whether through arguments or the physical comedy of a trip to the bathroom, the oppressive chauvinism of Iranian law is the butt of the joke—Panahi finds room for nuance and grace. (Rarely has turning on a radio carried so much dramatic weight.) There’s a distinct bittersweetness to the moments of victory, but Panahi underscores the possibilities of small understandings: In a brief escape, a play-by-play, or the uniting power of celebration, he hopes for a better tomorrow. (The movie itself is still waiting; it’s currently banned in Iran.) [Genevieve Valentine]

38. I Heart Huckabees (2004)

I Heart Huckabees is a punctuation in the career of director David O. Russell. Aside from his abandoned comedy Nailed (which has its own strange story), it’s the swan song of his oddball-auteur era, before he turned resolutely toward mainstream Hollywood filmmaking with The Fighter. And what a way to go out: Huckabees is a big existential brainteaser about the need for human connection and the individual’s ability to process both darkness and light in life. It features brilliant performances across the board, from Mark Wahlberg’s depressed firefighter to Lily Tomlin and Dustin Hoffman as metaphysical detectives rooting through Jude Law’s garbage to figure out what makes him tick. Seek it out, because, much like The Matrix, no one can really be told what I Heart Huckabees is—you have to experience it for yourself. [Alex McCown]

37. School Of Rock (2003)

Mike White was reportedly inspired to write School Of Rock after living next to Jack Black and listening to him run around, going off incessantly about rock music. The result is Black’s perfect starring role as wannabe rock star Dewey Finn, who impersonates his friend (White) as a posh prep school sub, drafting his students into his own band. Noted music lover Richard Linklater helms what is essentially a valentine to the inspirational power of rock. Black has never been more entertaining, putting his Tenacious D chops to good use while lecturing fourth-graders about the importance of Angus Young and Jimmy Page. Surprisingly, the show is stolen from even him by the amazing kid musicians, who learn one of life’s most important lessons: A great rock show can change the world. [Gwen Ihnat]

36. A Mighty Wind (2003)

Even by the most liberal view, A Mighty Wind is likely the third best film directed by Christopher Guest, squarely behind Best In Show and Waiting For Guffman (to say nothing of This Is Spinal Tap, which set the template for Guest’s style). That being said, this mockumentary about a reunion concert of ’60s folk singers stands head and shoulders above the rest in terms of the heart it brings to its proceedings. The cast of ringers includes Bob Balaban as one of a deceased folk patron’s anal-retentive children, Jane Lynch and John Michael Higgins as a former porn star and formerly abused child brought together by both folk music and a color-based cult, and a reunited Spinal Tap (Guest, Michael McKean, and Harry Shearer) as the aging Folksmen; and yet, somehow Eugene Levy and Catherine O’Hara’s “Mitch & Mickey” steal the show. It’s an improvisational tour de force. [Leonardo Adrian Garcia]

35. Kung Fu Hustle (2004)

When it comes to directing comedies, a steady hand behind the camera doesn’t just accentuate funny writing—it allows for more varied, dynamic jokes to flourish on screen. Just look at Stephen Chow’s martial arts cult classic Kung Fu Hustle, a wacky live-action cartoon about an amateurish nobody who becomes a kung fu master to stop an ax-wielding street gang from terrorizing 1930s Shanghai. Taking his cues from such diverse influences as the Shaw brothers and Chuck Jones, Chow creates an elastic world of expertly crafted wuxia fight sequences and Roadrunner-style chase scenes, with plenty of Three Stooges-esque slapstick to boot. Though grounded by a familiar hero’s journey, Hustle cleverly employs CGI effects to push the film to delirious, manic heights, moving from one crazy set piece to another. It’s the rare modern comedy that’s both a feast for the eyes and a workout for the funny bone. [Vikram Murthi]

34. Black Dynamite (2009)

Modeled on Rudy Ray Moore and D’Urville Martin’s uproarious Dolemite, Black Dynamite is the This Is Spinal Tap of clumsy grindhouse filmmaking, exaggerating its awkwardness (though not by much) while nailing its mix of amateurishness and ambition. Made to look like a lost blaxploitation cheapie, the movie pits vigilante Vietnam veteran, martial arts master, and CIA agent Black Dynamite (Michael Jai White, who also co-wrote) against a conspiracy to emasculate black men and hook orphans on heroin, which leads him through a whole lot of poorly lit sets all the way to Kung Fu Island and, finally, to the Nixon White House. As funny as the movie’s digs at the genre and dated setting may be, Black Dynamite’s best gags and meta-gags are the ones that play off the tradition of low-budget filmmaking as wish-fulfillment fantasy; Black Dynamite isn’t just a cartoonish badass, but the star of his own bizarre vanity project. [Ignatiy Vishnevetsky]

33. Punch-Drunk Love (2002)

There are several Adam Sandler movies where the actor’s misfit character boils over and violently lashes out, be it at a mugger, an opposing football quarterback, or Bob Barker. In Punch-Drunk Love, the put-upon Sandler character snaps in the face of his sisters’ relentless teasing and smashes up a bunch of windows with a crowbar, in what many read as a terrifying parodic riff on the star’s usual shenanigans. The thing is, though, it’s also pretty funny, distilling Sandler’s alternating meekness and aggression into a cathartic yet unsettling gesture. That tension vibrates throughout Punch-Drunk Love, one of the most nerve-jangling comedies ever made. Paul Thomas Anderson made his own cracked version of a feel-good Sandler picture, and somehow made it a convincing romance, too. The laughs don’t come from jokes, but rather from the way the whole thing teeters on the edge of violent tragedy. [Jesse Hassenger]

32. Kiss Kiss Bang Bang (2005)

With Kiss Kiss Bang Bang, onetime screenwriting juggernaut (and first-time director) Shane Black resurrected his signature tough-guy patter in service of a stunningly assured, Hollywood-set neo-noir buddy picture. He also resurrected faded stars Robert Downey Jr. and Val Kilmer. (Downey’s comeback took.) Small-time crook Harry Lockhart (Downey) and formidable L.A. private dick Gay Perry (Kilmer) are drawn into a suitably sleazy Tinseltown mystery that’s equal parts homage to and exemplar of Hollywood action thrillers. Black’s satirical meta-take on the genre that made him rich (even the title’s an in-joke) nonetheless vaults right over the self-awareness that pervades almost every line and twist, thanks to Black’s virtuosity and love for the movies he’s aping, and the never-better performances by the leads. Every time this endlessly re-watchable film seems poised to double back on itself one time too many, it’s revealed that everyone involved is actually steering just to the left of where you think they’re going. [Dennis Perkins]

31. The World’s End (2013)

The third effort from the more or less infallible filmmaking team of writer-director Edgar Wright and writer-star Simon Pegg, The World’s End is a sneakily incisive and tightly written metaphor for the homogenization of contemporary consumer culture and the allure of surrendering your will to a more powerful (if malevolent) force, something that has new resonance in the wake of Trump and Brexit. It’s also a surprisingly poignant exploration of the double-sided nature of nostalgia and the way time and circumstances drive apart even the best of friends. But perhaps more importantly, The World’s End is a science-fiction comedy that is genuinely hilarious. Pegg’s refusal to make his protagonist’s emotional neediness and desperation cute or even remotely appealing pays big comic, as well as dramatic, dividends. Like many of the best comedies, The World’s End is about something important, but it’s equally concerned with the equally important business of producing laughter. [Nathan Rabin]

30. Young Adult (2011)

Young Adult is not a nice movie. Its protagonist, Mavis Gary (Charlize Theron), is a mean, bitter, selfish woman, and the film isn’t kind to her either—a bold move in a media landscape where, five years later, female antiheroes are just coming into their own. Mavis is also a pioneering example of the woman-child, an emotionally stunted 37-year-old ghostwriter of Sweet Valley High-esque young-adult novels who’s obsessed with living out her fantasies of happily-ever-after with her high school boyfriend, Buddy Slade (Patrick Wilson). To Mavis, Buddy’s wife and child are just temporary setbacks—“We can beat this thing together,” she tells him, as if a newborn baby were a cancer diagnosis—and she’s not emotionally prepared for the fallout when those fantasies come crashing into reality. Both more barbed and more subtle than their work on Juno, Young Adult is among the best work of both screenwriter Diablo Cody and director Jason Reitman, and their re-teaming with Theron for the upcoming Tully is cause for celebration. [Katie Rife]

29. The Informant! (2009)

There are unreliable narrators, and then there’s Mark Whitacre (Matt Damon), the real-life corporate whistleblower whose sad story inspired The Informant!. From its jokey Marvin Hamlisch score to its cast, which is full of comedians playing it straight, Steven Soderbergh’s deceptively complex, 1990s-set farce seems designed to confound reactions; it may not be the funniest movie on this list, but it’s the one that gets the most out of a viewer’s expectations of comic tone. Soderbergh’s long-standing fascination with con artists, performers, and therapy reaches its apex in Whitacre, the goofy naïf whose self-deception makes him an uncommonly sympathetic antihero, even as the audience comes to trust him (and the movie) less and less. [Ignatiy Vishnevetsky]

28. O Brother, Where Art Thou? (2000)

The film that launched a thousand bluegrass revivalists, the Coens’ O Brother, Where Art Thou? loosely riffs on The Odyssey for this goofy, Depression-era adventure of three treasure-seeking escaped convicts: naïve Delmar (Tim Blake Nelson), irascible Pete (John Turturro), and loquacious, Dapper Dan-greased Ulysses Everett McGill (George Clooney). The leads deliver laughs, no matter how over-the-top their performances—Clooney is at his wide-eyed, hammy best here—and the rambling, sepia-toned film tightens as the boys’ plotline intersects with that of politicking Gov. Pappy O’Daniel. Like Ulysses’ ex-wife, whose loyalty flips according to her beaus’ prospects, the constituents are fickle, as likely to support a man buddying with a popular band at the right time as they are someone they believe in. Lessons to remember this election year: One’s success may depend more on serendipity than actual beliefs, and even so-called bona fides can get dropped for fast-talking shysters. [Laura Adamczyk]

27. Idiocracy (2006)

It’s become a cliché to end every discussion of some distressing recent cultural development by saying, “Idiocracy was right.” But dang it, true is true. From the decline in basic literacy to the way that politics and cable news increasingly resemble the worst of reality TV, the dire predictions in writer-director Mike Judge’s dystopian comedy keep coming to pass. If there’s any solace to all this, it’s that Idiocracy itself seems relatively sanguine about the world of tomorrow. As an unfrozen 20th-century everyman (Luke Wilson) navigates a 25th century dominated by mega-corporations, celebrities, and fart jokes, he maintains some hope that humanity is still smart enough to recognize the need for change. The film is as angry as it is quotable, but it isn’t wholly depressing, because Judge kind of admires how we can be ingenious even in our ignorance. [Noel Murray]

26. Ghost World (2001)

Drawn from the indie comics of Daniel Clowes and directed by Terry Zwigoff—up until that point a documentarian whose most famous work was a profile of underground cartoonist R. CrumbGhost World captures a very specific worldview and aesthetic with uncanny precision. (Zwigoff’s casting is particularly spot-on.) Perpetually deadpan, Bollywood-obsessed Enid (Thora Birch) and her best friend, the equally cynical but more conventional Rebecca (Scarlett Johansson), are fresh out of high school; and now that they’re free of the prison-like structure that oppressed them for four years, they’re free to do whatever they want—although Enid’s not sure she knows what that is. In the meantime, she takes a remedial art class taught by Illeana Douglas that provides some of the film’s most purely comedic moments, and strikes up an uneasy pesudo-romance with middle-aged record collector Seymour (Steve Buscemi) that provides some of the film’s most unbearable pathos. The Ghost World of the title turns out to be both cartoonishly quirky and emotionally resonant. [Katie Rife]

25. What We Do In The Shadows (2014)

Cinematic vampires are often seen in their finest, most glamorous form. But with What We Do In The Shadows, Taika Waititi and Jemaine Clement attempt to (re)humanize the immortal beings by placing them in the most mundane circumstances. The writer-directors wring plenty of sympathy (and laughs) for the devils, who worry about housekeeping and romance while also evading vampire hunters. The central quartet suffer from many of the same insecurities as the humans they feed on, along with a deadly photosensitivity. And they’re not much better at resolving those problems, even with tens of thousands of years of experience. The absurdist mockumentary began as a short, but as a feature-length film, the premise grows more layered instead of wearing thin. [Danette Chavez]

24. Obvious Child (2014)

Obvious Child thumbs its nose at the controversy of abortion, treating it like the everyday occurrence it is. Jenny Slate, who previously stole scenes in Parks And Recreation and Kroll Show, got a breakout role as Donna, a stand-up comic who meets Max (Jake Lacy) after delivering a terrible, alcohol-soaked set about her ex-boyfriend. What follows is more or less typical (though very smart) rom-com fare, except that Donna explores her post-hookup relationship with Jake while navigating getting an abortion. Donna never once questions her choice, and the naturalness with which she talks to her friend (Gaby Hoffmann) and mother (Polly Draper) about terminating her pregnancy makes this otherwise low-key comedy feel revolutionary. Writer-director Gillian Robespierre engages a sensitive subject with humor and wit, avoiding what could have been “a movie about abortion” for something far more important: a good rom-com that just happens to contain an abortion in it. [Caitlin PenzeyMoog]

23. Walk Hard: The Dewey Cox Story (2007)

“Dewey Cox needs to think about his entire life before he plays.” Drawing on everything from the relentless foreshadowing of John Carpenter’s Elvis to the extended flashback framing device of Walk The Line, Jake Kasdan and Judd Apatow’s parody of musician biopics skewers the genre’s clichés, formulae, and tropes through the story of dopey country-rock-pop-folk star Dewey Cox (John C. Reilly). With its hilariously clunky expository dialogue, gratuitous historical cameos, and absurdly unconvincing casting, Walk Hard is both an affectionate riff on decades of popular music and a surprisingly piercing takedown of the phoniness of the Hollywood biopic. [Ignatiy Vishnevetsky]

22. Burn After Reading (2008)

Released just seven months after No Country For Old Men dominated the 80th Academy Awards, the Coen brothers’ aggressively goofy parody of self-serious espionage thrillers was largely dismissed as a cute trifle. Look beyond its ensemble of clueless narcissists (including a never-funnier Brad Pitt as the world’s most cheerfully moronic gym rat), however, and it’s clear that Burn After Reading, in the tradition of satires like Dr. Strangelove, wildly exaggerates governmental paranoia and incompetence as a means of underlining how readily they can lead to pointless tragedy, especially when they intersect with civilian greed. The plot, in which the memoir-in-progress of an ex-CIA analyst (John Malkovich) winds up in the hands of a gym employee (Frances McDormand) obsessed with cosmetic surgery, is so hilariously convoluted and absurd that the movie stops cold more than once so that an imperturbable CIA officer (David Rasche) can try to explain exactly what the hell is going on, for the benefit of his deeply bewildered boss (J.K. Simmons). And they don’t even know what George Clooney’s treasury agent/U.S. marshal is secretly up to, skulking around the perimeter of the narrative—a surreal bit of intrigue that pays off in a truly unforgettable sight gag. [Mike D’Angelo]

21. Step Brothers (2008)

The funniest moments of Adam McKay’s films with Will Ferrell are in the downtime between absurdist set pieces, when Ferrell’s allowed to riff on something so mundane, you can practically smell the money burning. In this regard, he has no better scene partner than John C. Reilly, who perfectly matches him, improvised inanity for inanity. And there’s no better showcase for their flights of nonsense than this 2008 film about two 40-going-on-12-year-olds forced to live with each other when their parents get married, only to become allies in a war against adulthood. As Ferrell and Reilly karate fight, record dumb rap songs, teabag drum sets, and generally act like swaggering idiots for 90-plus minutes, the film similarly just sort of dicks around with almost zero pretense to growth or narrative. But that leaves—to paraphrase one of the film’s many quotable lines—so much more room for activities, with a cast stacked with people clearly enjoying themselves (including Richard Jenkins, Adam Scott, Kathryn Hahn, and Rob Riggle) firing off enough nested jokes to make Step Brothers endlessly rewatchable—and as inexplicably magical as the fucking Catalina wine mixer. [Sean O’Neal]

20. The 40-Year-Old Virgin (2005)

The Judd Apatow style, mostly characterized by films that lurch from one comic set piece to another for a half-hour too long, eventually sagged under its own thoughtful weight. But to watch Apatow’s feature directorial debut, The 40-Year-Old Virgin, is to understand why it became his template. It’s quite long for a ribald comedy, but it tells two equally weighted love stories. There’s the one between Andy (an ascendant Steve Carell) and Trish (Catherine Keener), the object of his inexperienced affection, and the one between Andy and his co-workers (Seth Rogen, Paul Rudd, and Romany Malco), the rowdy guy friends he’s never had. Some of the zestiest scenes are totally immaterial to either story, and yet it’s hard to imagine the movie without them. That includes the lengthy ending tribute to Hair, the perfect conclusion to a film all about how satisfying it can be to wait for the climax. [Joshua Alston]

19. The Lobster (2015)

For his English-language debut, Greek director Yorgos Lanthimos (Dogtooth) made the genre of dystopian sci-fi all his own, imagining an unforgiving near future in which single people must pair up or else face the ultimate punishment: a surgical procedure to transform them into the animal of their choosing. The Lobster’s individual lonely-hearts interactions—filled as they are with too-literal small talk and defeated body language—prove amusing on their own. But the film is most savagely funny as a broadband satire: Lanthimos pulls no punches in exposing the tyranny of conventional mating rituals, as well as the superficial ideas of coupledom perpetuated by a culture of dating apps and reality television. It’s a testament to The Lobster’s very incisiveness that the film, which hit theaters just this spring, has already made its mark as one of the century’s finest social critiques. [Ben Mercer]

18. Mean Girls (2004)

Though it pretty much marked the end of Lindsay Lohan’s career—for now, at least—Mean Girls also marked the beginning of Tina Fey’s emergence from the Saturday Night Live bubble. Previously, she’d been the whip-smart head writer of the show who popped up once an episode to trade barbs with Jimmy Fallon as part of Weekend Update. With Mean Girls, Fey became not only the writer of a hit comedy, but the co-star of one as well, thus proving herself to be a substantial force in Hollywood. It’s with good reason: Mean Girls is a sharp teen comedy with a dark edge, a movie that both skewers society and seeks to make it better. With stellar performances from Rachel McAdams, Amy Poehler, and Lizzy Caplan, Mean Girls has since become more than just a movie, having gifted lines like “On Wednesdays we wear pink,” and “You go, Glenn Coco,” to the pop culture lexicon. [Marah Eakin]

17. In Bruges (2008)

Marked by sudden but never muddled tonal shifts, In Bruges is part thriller, part buddy movie, part meditative morality tale, and all dark comedy. Ray (Colin Farrell) is a hit man stashed away in Bruges at Christmastime after a botched assignment, and his fluent, even gleeful, profanity hangs incongruously against the city’s fairy-tale beauty. He’s callow and crude, but also coltishly appealing. As Ken, Ray’s mentor, Brendan Gleeson is mature and level-headed, determined to carve out a moment of peace for both of them in this picturesque setting. Writer-director Martin McDonagh and cinematographer Eigil Bryld make lavish use of the city’s charms, peering up to the heights of Bruges’ medieval spires or down to cobblestone streets, creating a visual sensibility as vertiginous as the film’s plot and mood. In Bruges is bleakly hilarious and affecting, harsh and human. [Emily L. Stephens]

16. The Grand Budapest Hotel (2014)

With its storybook settings, pastel walls, and cultural mélange, mainland Europe is fertile ground for Wes Anderson’s whimsical pastiche. In The Grand Budapest Hotel, inspired by Stefan Zweig, Anderson recreates the continent’s 20th century as a slapstick comedy of manners that packs on tragedy as it’s passed down through the generations. War is building, borders are closing, and culture is disappearing—but not if Ralph Fiennes’ Monsieur Gustave has anything to say about it. Gustave is one of Anderson’s (and Fiennes’) finest characters, a concierge extraordinaire who clings to the trappings of an old world order in the face of a base new one. He’s joined by a roster of Anderson regulars like Jason Schwartzman as a bored Frenchman and Willem Dafoe as a crypto-Transylvanian enforcer. Everything from Lubitsch to giallo is alive in The Grand Budapest Hotel, a bittersweet comedy about the tremendous value of collective memory. [Brandon Nowalk]

15. Team America: World Police (2004)

In an age when practically everything is sifted for potentially career-destroying offense, 2004’s Team America: World Police already feels like it’s from another era—a wild, pre-Twitter time when you could sing about everyone having AIDS and reduce Arabic language to “durka-durka” gibberish without worrying about the ensuing protests. Offending everyone equally has long been Trey Parker and Matt Stone’s goal, after all, and even more than South Park, their film mocking America’s post-9/11 foreign policy has a carpet-bombing approach to pissing absolutely everyone off on its way to Mission Accomplished. Terrorists, patriots, Kim Jong-Il, and leftist celebrities all take a relentlessly savage beating, tempered only slightly by the fact that they’re played by cheesy marionettes. Much like South Park’s animation, this crudeness gives Team America’s proud political incorrectness, scatological violence, and assorted puppet-fucking a feeling of id-driven abandon—like a kid smashing his toys together, or the U.S. invading Iraq. But it also doesn’t undercut moments like the “Dicks, Pussies, And Assholes” monologue (as astute a delineation of international relations as ever written), nor does it ever stop Team America from being the exact, gloriously juvenile satire a decidedly puerile political system needed, both then and now. [Sean O’Neal]

14. Bridesmaids (2011)

Paul Feig has a right to be irritated by the sexist insults lobbed against his all-female Ghostbusters remake, not only out of principle, but because he’s worked so hard to break down comedy’s gender divide. Prior to Bridesmaids, Feig’s breakthrough film, female comedy characters were usually only included in gross-out humor if the joke was on them. (See Cameron Diaz’s seminal pomade in There’s Something About Mary.) In Bridesmaids, the ladies do the dirty work, as in the infamous scene where a glamorous dress-fitting devolves into a scatological mob scene. The sequence isn’t poop for poop’s sake; it’s a reminder that Annie (Kristen Wiig) and her friends are whole, messy people, not thinly drawn love interests or co-workers. The film’s empathetic exploration of female friendships is essential to its hilarity, which is why the Ghostbusters backlash is so frustrating. Bridesmaids proved women too could be the life of the potty. [Joshua Alston]

13. Hot Fuzz (2007)

“Ever fired your gun in the air and yelled ‘Aaaaaaah’?” That’s Police Constable Danny Butterman (Nick Frost), attempting to bond with his new partner, Sgt. Nick Angel (Simon Pegg)—and subliminally articulating the philosophy of gleeful chaos that infuses Edgar Wright’s Cornetto trilogy. Like any good pop-culture acolytes, the Spaced alums make sure the second entry in their cinematic troika represents several pinnacles for the quasi-franchise: the most entertaining action sequences, splatter effects that manage to top Hot Fuzz’s overtly horror-themed predecessor, and the quintessential deployment of Pegg and Frost’s Mutt-and-Jeff schtick. (One’s a straitlaced cop who plays by the rules; the other plays by “rules” from the books of Bigelow, Black, and Bay.) Hot Fuzz swirls ’80s blockbuster excess, ’70s thriller paranoia, and evergreen satire of provincial conservatism into a moodily lit, dynamically edited confection of spoofery. The flavorful goo holding it all together is the connection between two performers and one filmmaker who truly know what it means to fire their guns in the air and yell “Aaaaaaah.” [Erik Adams]

12. Adaptation. (2002)

Screenwriter Charlie Kaufman and director Spike Jonze’s screwy adaptation of Susan Orlean’s digressive nonfiction book The Orchid Thief finds a smart, funny way to work in all the brainstorming notes that are sometimes the best product of the writing process. By focusing Adaptation. on Kaufman himself (played by a lumpy-looking Nicolas Cage), the film captures the basic details of Orlean’s quirky story about a Florida flower thief, and it gets at what such a tale really has to say about biological mutation, chemical attraction, and the power of choice. By the third act, the movie takes a tongue-in-cheek Hollywood turn, inspired by screenwriting guru Robert McKee and Kaufman’s much more confident (and fictional) twin brother, Donald. But really every piece of Adaptation. is about the same thing: how life, love, and creativity are subject to the demands of Darwinian evolution, whether we like it or not. [Noel Murray]

11. Superbad (2007)

None of the many Apatow-affiliated comedies better capture the sensibility of that comedy guru’s exemplary TV work (while also taking advantage of cinema’s limited frame) than this 24-hour look at two high school seniors on a quest for booze and/or sex. Superbad has a lot of voices in the mix: producer/mentor Apatow, screenwriters Seth Rogen and Evan Goldberg, stars Michael Cera and Jonah Hill, and director Greg Mottola, among others. They all work so seamlessly together that terrific writing, acting, and direction turns almost invisible. Watching excerpts of an early read-through with different actors on the DVD reveals how much improvised-sounding dialogue was actually scripted—and shows just how natural Hill and Cera make these lines sound. Together, everyone involved makes Superbad funny in the way that hanging out with your goony teenage friends is funny, full of profanity, pop-culture references, and weird shared history. Apatow may not work on Freaks And Geeks anymore, but Mottola and company revived that show’s spirit for what turns out to be a great, even tender, movie about male friendship. [Jesse Hassenger]

10. Borat: Cultural Learnings Of America For Make Benefit Glorious Nation Of Kazakhstan (2006)

It’s a shame that Borat is remembered mostly for catchphrases (“My wife!”) that signify hacky comedy, because the 2006 movie perfectly distills what’s been so dangerous, groundbreaking, and ridiculously funny about Sacha Baron Cohen’s career. As a racist rube, the title character is able to bring out the worst—and, strangely, sometimes the best—in the real-life Americans who were mostly unwitting participants in the filming. Sure, it’s not actually a documentary, but Borat does offer some of the “cultural learnings” that its title promises: When confronted with someone as hapless and naïve as Baron Cohen miraculously makes Borat out to be, some Americans confirm the worst assumptions about them, like the frat dudes who sued the production, or the mega-church creationists. Others prove exceedingly polite, like the Southern woman who keeps it together even as Borat brings a bag of his own shit and, later, a prostitute to her dinner table. It’s so much more—and so much funnier—than “Niiice!” [Josh Modell]

9. Scott Pilgrim Vs. The World (2010)

It’s a story as old as love itself: (Canadian) boy meets (American) girl; boy fights super-powered avatars representing the ghosts of relationships past; boy and girl walk off into the sunset underneath the CN Tower. Edgar Wright’s perfect adaptation of Bryan Lee O’Malley’s graphic novel series may be the most unrepentantly Toronto-centric movie ever made, mining civic landmarks for sight gags and pathos (let he who has never caused a scene at Lee’s Palace cast the first stone), while the romantic pairing of the eponymous hoser hero (Michael Cera in the slacker-Romeo role he was born for) with ex-NYC hipster Ramona Flowers (Mary Elizabeth Winstead, ditto as an endearingly obscure object of desire) is the very picture of intracontinental contentment. Bonus points for feeling fleet and funny despite running nearly two hours, and also for boasting that rarest of 2000s-era amenities: a killer indie-rock soundtrack, topped off by Brie Larson as Envy Adams, singing Metric’s “Black Sheep” in a brilliantly cut split-screen sequence. [Adam Nayman]

8. High Fidelity (2000)

Making relentless navel-gazing into engaging comedy is no mean feat, but High Fidelity manages to pull it off thanks to its refusal to empathize completely with John Cusack’s sad-sack protagonist. Even as the camera indulges Rob’s obsessive “Top 5” list-compiling and fourth-wall-breaking whines about the women who got away, Stephen Frears’ adaptation of Nick Hornby’s novel recognizes the depths these reveal about his own self-centeredness—and much of the bittersweet humor of the film comes in watching him realize it as well. There are also easier laughs to be had in Jack Black and Todd Louiso’s snobby record store clerk archetypes, plus Tim Robbins as every patchouli-soaked yogi you’ve ever brushed up against at Whole Foods. But as with Cusack’s mix-tape-making man-child, High Fidelity grounds even these caricatures in emotional stakes that feel as lived-in as the movie’s Chicago setting. As a result, what could have been gimmicky and artificial instead comes off like a film even its elitist characters can’t totally sneer at—a genuine romantic comedy for the Pitchfork crowd. [Sean O’Neal]

7. Anchorman: The Legend Of Ron Burgundy (2004)

Will Ferrell and Adam McKay have taken on more relevant topics than the cluelessness and sexism of ’70s news anchors: American exceptionalism in Talladega Nights, the financial crisis in The Other Guys, and the 24-hour news cycle in the belated Anchorman 2. By comparison, the original Anchorman might feel positively esoteric… were it not so boundless in its hilarity. The first McKay-Ferrell joint finds the SNL buddies following their whims, which is probably why it had to be assembled from footage so multitudinous that several fully excised subplots are visible in a separate compilation film. Their sheer volume of bizarre, brilliant comic ideas means staging a ridiculous and deadly multi-station anchorman brawl, then deconstructing its escalation over beers in the next scene; jumping into animation to convey the mind-blowing power of the sex Ron Burgundy (Ferrell) enjoys with his professional rival Veronica Corningstone (Christina Applegate); and drop-kicking a dog off of a bridge, among other digressions. While Burgundy hits rock bottom (complete with beard and chugging of poorly chosen milk), Ferrell and McKay quickly ascended to a career peak. [Jesse Hassenger]

6. Frances Ha (2012)

On paper, Frances Ha sounds like a movie we’ve seen a million times before: An aimless twentysomething flits around—mainly in New York City with pit stops in Poughkeepsie, Sacramento, and Paris—living life and learning lessons. But director Noah Baumbach and star Greta Gerwig, who wrote the film together, bring a rare deftness and generosity to Frances’ story, taking a character who could have become a caricature of navel-gazing privilege and giving her real warmth and humanity. That’s mainly due to Gerwig’s affectionate, accomplished performance, although it helps that Frances Ha focuses on the question your typical mumbly New York indie never seems to ask: namely, where this aspiring professional dancer is going to live, and how the hell she’s going to pay for it. Frances’ couch-surfing adventures form a sort of satirical field guide to the modern hipster in all of its sometimes-ridiculous forms, driven by laugh-out-loud funny conversations so natural they seem improvised, even though they’re not. It may be the pinnacle of Baumbach and Gerwig’s creative partnership so far. [Katie Rife]

5. Shaun Of The Dead (2004)

Edgar Wright is the most represented filmmaker on this list, and with good reason: The English director’s genre-homage comedies aren’t just entertaining and really damn funny, but also bursting with creative energy and visual wit. Part zombie horror send-up, part loving homage, Wright’s breakthrough pits an aimless everyman (Simon Pegg, in a star-making performance) against the hungry undead, all the while forcing him to confront his feelings about his girlfriend, best friend, family, and life. Tightly constructed and informed by deep affection, the first entry in Wright’s so-called Cornetto trilogy is a movie in love with the stuff that goes into making an ingenious shot, a neat effect, or a good gag. [Ignatiy Vishnevetsky]

4. Best In Show (2000)

When Waiting For Guffman picked up where This Is Spinal Tap left off, it presaged a wave of documentary (and mockumentary) products detailing the lives of everyday folks who yearn for nothing more than their own personal spotlight. A year before David Brent’s BBC debut (and a month after Susan Hawk called Richard Hatch a snake in the final Tribal Council of Survivor’s first season), Guffman director Christopher Guest moved from the earnestly untalented denizens of Blaine, Missouri, to the egos, left feet, and Busy Bees that flock to the fictional Mayflower Kennel Club Dog Show. Guest and his cast shot hours and hours of footage for Best In Show, and it comes together so seamlessly, it’s easy to forget that 50 minutes pass before the whole ensemble shares the same scene. The results are an embarrassment of improvised riches, from Fred Willard’s numbskull color commentary as broadcaster Buck Laughlin (“Why didn’t he put the bloodhound—put on one of those Sherlock Holmes hats and put a little pipe in his mouth?”) or “catalog people” Hamilton and Meg Swan (Michael Hitchcock and Parker Posey) describing their inter-Starbucks meet-cute. Even the stuff that didn’t make the final cut deserves a blue ribbon: A deleted scene involving Guest’s character and his beach ball collection could be the basis for an entirely separate, equally hilarious film. [Erik Adams]

3. In The Loop (2009)

Veep creator Armando Iannucci’s only movie to date expands his BBC series The Thick Of It—a blistering satire of British political gamesmanship—onto the international stage, taking on the war in Iraq (which we were still very much in the thick of at the time). Familiarity with the small-screen version isn’t necessary, as roughly half of the movie takes place in the U.S.; Iannucci introduces several new characters, including a none-too-hawkish general played by the late James Gandolfini. Still, as on the show, it’s primarily Director Of Communication Malcolm Tucker’s cavalcade of extravagantly creative and profane insults that make In The Loop such a gut buster. As played by Twelfth Doctor Peter Capaldi, Malcolm wields words like a samurai sword, eviscerating everyone who crosses his path; “Allow me to pop a jaunty little bonnet on your ‘purview’ and ram it up your shitter with a lubricated horse cock,” constitutes a fairly mundane verbal attack by his standards. If that’s not the sort of thing you find funny, well, as he would say, fuckity bye! [Mike D’Angelo]

2. The Royal Tenenbaums (2001)

Royal Tenenbaum (Gene Hackman) is kind of a sonofabitch. He’s also the type of father who doesn’t hesitate to play favorites among his children. For audiences, however, ranking the fallen-from-grace progeny of Wes Anderson’s winsome 2001 masterpiece would be no easier than determining the film’s funniest sight gag (the BB? The Dalmatian mouse?), the best needle-drop from its soundtrack (Nico? Elliott Smith?), or its most quotable line of deadpan dialogue (maybe that bit about General Custer). Structured like a novel but staged like a storybook put into motion, The Royal Tenenbaums is the moment that Anderson, fresh off the critical (but not commercial) success of Rushmore, fully matured into his signature style—an M.O. that’s tempting to imitate, impossible to match, and identifiable from just a single carefully composed frame. In the years after, he’d apply his gift for bottom-up world-weaving to everything from a transcontinental train to a foxhole to a colorful luxury hotel. But none of these meticulously designed comedies quite surpassed the balancing act Anderson achieved with Tenenbaums, in which a dream ensemble—led by Hackman, gut-bustingly unscrupulous—brings a family of cartoon cutouts to heartbreaking three-dimensional life. Picking a favorite among Royal’s offspring is tough. Picking a favorite among Anderson’s, not so much. [A.A. Dowd]

1. Wet Hot American Summer (2001)

When the kids of Camp Firewood snuck out of the Maine wilderness and onto a whopping two screens on July 27, 2001, they ran into a vision of their future. And it wasn’t the post-credits stinger where 1991 J.J. (Zak Orth) forgets to make it his beeswax to be there by 9:30—it was Monty Python And The Holy Grail, which was enjoying a brief theatrical revival the same weekend. Fast forward a decade and a half, and Wet Hot American Summer and Monty Python And The Holy Grail stand shoulder to shoulder as eminently quotable, endlessly rewatchable, deeply beloved cult classics. Caped Boy, Medieval Kid, and Mork Guy should be proud.

So should director David Wain, his co-screenwriter Michael Showalter, and a dynamite cast—there’s no way a 2016 comedy starring Paul Rudd, Elizabeth Banks, Bradley Cooper, and Amy Poehler would have the unceremonious roll out Wet Hot American Summer received in 2001. But none of their subsequent efforts—excepting Wet Hot’s Netflix prequel—squares their divergent tones, stretches their set pieces, or assembles their montages as expertly as this chronicle of the last day of summer camp circa 1981. The film’s silly-smart tug-of-war favors non sequitur and absurdity, while still dropping bizarrely specific allusions (“I am not joking. I am not Ruth Buzzi standing here!”) and deploying kitschy fashions as sight gags. Michael Ian Black’s red short shorts are one of a kind, as are Wet Hot’s most storied tangents: Rudd’s cafeteria tantrum, Janeane Garofalo and Joe Lo Truglio demolishing the infirmary, Christopher Meloni’s full-bodied inhabitation of sweater-fondling cook Gene. At a turning point in the film’s main storyline, Gene promises to teach mopey protagonist Coop (Showalter) about something he calls “the new way.” It was years before anyone touched the Pythons’ Holy Grail; everybody’s still playing catch-up with Wet Hot American Summer’s new way. [Erik Adams]

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