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The 70 Best Comedies of the 21st Century

If it's true that laughter is the best medicine, consider this list a panacea.

The best comedies of the 21st century include Support the Girls, Sorry to Bother You, and The Grand Budapest Hotel

30. “The Big Sick” (2017)

Emily Gordon and Kumail Nanjiani nabbed a Best Original Screenplay nomination for synthesizing their harrowing true romance into a sharp and winsome comedy about a courtship that begins with a culture clash and survives a coma. After Gordon and Nanjiani wrote the script as an intense form of couples therapy, uber-producer Judd Apatow and director Michael Showalter whipped it into shape and cast Zoe Kazan as the young woman who falls for a Pakistani-American comic and Uber driver (Nanjiani). When she’s hospitalized, her parents (Holly Hunter and Ray Romano) learn to appreciate her tortured lover’s affection for their sleeping beauty before she comes back to life. —AT
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29. “Team America: World Police” (2004)

During the buildup for the invasion of Iraq, filmmakers Trey Parker and Matt Stone wrote an R-rated puppet movie that was a sophisticated deconstruction of the cliches of Jerry Bruckheimer action pictures like “Armageddon.” The plot is simple: When Team America learns that ruthless North Korean leader Kim Jong Il is disseminating weapons of mass destruction, it recruits a Broadway actor to join the international police squad to help save the world. This politically incorrect comedy is all about getting laughs from blowing up elaborate sets of Big Ben, the Great Pyramids and the Eiffel Tower — as well as 22-inch puppets who resemble outspoken liberal celebrities such as Janeane Garofalo, Tim Robbins and Michael Moore. “America: Fuck yeah!” —AT
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28. Wet Hot American Summer (2001)

It’s tough going picking out the best gag in David Wain’s cult comedy classic, mostly because this wacky summer camp send-up doesn’t take its foot off the gas for even a minute. From an incredible twist on the timing implications of the montage, the lead up to the world’s worst (or best?) talent show, to a running joke involving the fraught background of no less than Christopher Meloni as the camp’s haunted cook, every joke lands with resounding comedic precision.

Thank Wain and his merry band of collaborators, including Michael Ian Black, Michael Showalter, Ken Marino, and Joe Lo Truglio, plus perpetual comedic all-stars like Janeane Garofalo, David Hyde Pierce, Molly Shannon, Paul Rudd, and Amy Poheler (and the wholly unexpected and deeply inspired casting of a young Bradley Cooper), for making this crazy campside stew work as well as it does. Nothing is out of place, even the stuff that seems truly insane — a sub-sub-plot about Garofalo and Pierce’s characters taking time to bone up on the others’ niche careers only gets funnier with time, the jokes about “Godspell” are as uproarious as ever. You don’t have to be a former camper to appreciate its dizzy jokes, but it can’t hurt. Capture the flag, anyone? —KE

27. “Walk Hard: The Dewey Cox Story” (2007)

On its face, a simple parody of the musical biopic genre made famous by the Academy Awards bait of “Ray” and “Walk the Line,” Jake Kasdan’s “Walk Hard: The Dewey Cox Story” elevates past lesser parody films thanks to the bravura performance of John C. Really as the title character. But the real star of the show here is the amazing soundtrack composed for the film by Dan Bern and Mike Viola (among others) that satirizes rock-and-roll from its salad days to the present day. Songs like “Walk Hard,” “Royal Jelly,” and “Beautiful Ride” aren’t simply ringers for insertion into the catalogues of Johnny Cash, Bob Dylan, and Glen Campbell, respectively, they’re also great songs that can be enjoyed free of their referential context. In fact, perhaps the music therein allows “Walk Hard” to sit on the very same shelf as the films it parodies, and well above some: (cough cough) “Bohemian Rhapsody” (cough cough). —LAG

26. “Superbad” (2007)

Michael Cera may not actually be the fastest kid alive, but the aughts’ most hilarious movie about teenagers being teenagers was a runaway success all the same. And it wasn’t just McLovin that made it so: Cera and Jonah Hill’s bromance was as genuinely sweet as it was startlingly accurate to the way teens spoke and behaved back then. (As someone who was 19 at the time, I’m more qualified to comment on this than I should probably admit.) —MN
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25. “Girls Trip” (2017)

Editorial use only. No book cover usage.Mandatory Credit: Photo by Michele K Short/Universal/Kobal/Shutterstock (8970068v)Tiffany Haddish"Girls Trip" Film - 2017

There’s plenty of star power behind “Girls Trip,” including always-bankable director Malcolm D. Lee and big names like Queen Latifah and Jada Pinkett Smith, but it’s impossible to deny its biggest breakout: then-newcomer Tiffany Haddish, who made off with not only the comedy’s best lines and bits of physical humor, but its most eye-popping performance. Haddish’s zippy charisma sets the film’s tone early, zinging between bouts of physical comedy (no one lunges at a co-star with as much pizzazz as Haddish) and wonderful off-color one-liners that are as shocking as they are masterfully delivered. Later in the film, Haddish serves up what will likely become contemporary cinema’s best example of how to use fruit to simulate sex acts (sorry, “American Pie”), a sequence so deliciously raunchy that it’s worth the price of admission alone.

Those pure laughs are more than enough to sustain a comedy so crystalline that it was a classic the minute it hit screens, as “Girls Trip” nails laugh after laugh even amidst — and oftentimes because of — dramatic issues that wouldn’t be out of place in a Lifetime movie. As the film’s central ladies make their way through all the glory that New Orleans’ Essence Fest has to offer, including run-ins with a slew of big talents in a seemingly never-ending parade of cameos (Diddy makes off with the best one, predictably bolstered by Haddish’s involvement) and at least one wildly ill-conceived adventure fueled by absinthe, “Girls Trip” keeps the momentum whirling ever onward into the next big comedic set piece. Even as it all ends with a heartwarming reveal, that doesn’t dilute its more raucous sensibilities; it only makes it more clear why Lee and his ladies should turn “Girls Trip” into a franchise that can spawn more uproarious vacations. —KE
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24. “In Bruges” (2008)

Irish directors bring out the best in fellow countryman Colin Farrell. Playwright-director Martin McDonagh, made his film feature directing debut with this anarchic black comedy (and earned an Oscar nomination for his screenplay), handing Farrell his richest comedy role to date as a soulful hitman. Farrell’s Ray is sweetly violent as he hangs out in dullsville Belgium with his partner Ken (Brendan Gleeson), making mischief and mayhem while seeking an ounce of redemption. —AT
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23. “The 40-Year-Old Version”

Radha Blank appears in <i>The 40-Year-Old Version</i> by Radha Blank, an official selection of the U.S. Dramatic Competition at the 2020 Sundance Film Festival. Courtesy of Sundance Institute | photo by Eric Branco.All photos are copyrighted and may be used by press only for the purpose of news or editorial coverage of Sundance Institute programs. Photos must be accompanied by a credit to the photographer and/or 'Courtesy of Sundance Institute.' Unauthorized use, alteration, reproduction or sale of logos and/or photos is strictly prohibited.

Radha Blank won the Directing Award in the U.S. Dramatic section of Sundance 2020 and no wonder: here was a comedy shot in black-and-white that expressed something vividly, vibrantly new. Blank stars as a version of herself who’s a playwright, but hasn’t had one of her plays produced in a very long time. She’s maybe cherishing that 30 Under 30 award a little too much, the further she gets from having received it. “I just want to be an artist!” she sobs at one point. Yet that’s hard to do when she’s under pressure to write “a Harriet Tubman musical” — something Blank’s been asked to do in real life — and told by one middle aged white male producer that her work is “inauthentic… I asked myself, did a Black person write this?” So Radha ends up cutting a rap mixtape under the name Radhamus Prime, and finds a new creative release. Blank delivered one of the definitive “laugh, or otherwise you’ll cry” comedies of the 21st century. —CB

22. “Harold and Kumar Go to White Castle” (2004)

How far would you go for some sliders? In “Harold and Kumar,” a couple of stoners getting the munchies is treated as an odyssey of epic (and hilarious) proportions. The unlikely franchise-starter has endeared itself to cannabis enthusiasts as well as those who don’t partake, inspiring moviegoers to Just Say Yes for more than a decade; given the strides that marijuana (both medicinal and otherwise) has made in recent years, you could even say that the cult classic was ahead of the curve. —MN
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21. “O Brother, Where Art Thou?” (2000)

Packed with corn-pone humor and catchy southern roots music, this rollicking Coen brothers 1930s adaptation of Homer’s “The Odyssey” follows a gang of escaped dimwit prisoners led by pomaded charmer Everett McGill (George Clooney), who tries to get back his wife (“Raising Arizona” star Holly Hunter) by singing her into submission. T-Bone Burnett’s best-selling soundtrack won the Grammy for album of the year and cinematographer Roger Deakins nabbed an Oscar nomination for his pioneering digital alterations to this Working Title film’s color palette. But as always, helping Clooney, Hunter, Tim Blake Nelson, John Turturro and John Goodman earn this meandering fable’s countless laughs was the main goal.  —AT
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