The tough part about assembling this list was excluding unintentional comedies; I mean, some of the hardest laughs you’ll ever experience come during Pearl Harbor’s love scenes. But in truth, there were a lot of great comedies in the 2000s, intentional ones, and they fell into every category. Some were straightforward, some were absurd, some were genre hybrids, and some snuck up behind you with heartbreak. But they’ve all got something in common: They’re smarter than you’d think. These are subversive, interesting movies, whether they’re making dick jokes or telling stories about lost love.
And they are all, of course, funny. That’s something that came in handy during the decade, because let’s face it, 2000-09 was just a horrible span of years, bookended by war and financial ruin and filled in between with every kind of disgusting letdown imaginable. It was an era of lowered expectations on every front, and these comedies were welcome oases in a desert of growing idiocy. They were chances to get away, but they were also defining moments of the era. They’re elemental movies that dominated their field and proved to be a cut above the rest, and also in the sense that some of them are the most basic distillation of their own little sub-genres. (Interestingly, they’re all from 2005 or earlier; I don’t know what to make of that except that some films need time to become revered, though the second half of the decade was also a bit weaker than the first.) Most of them aren’t as serious as the movies that tend to be touted as the best of the year or decade — those peaks are often reserved for dramas — but that’s a little unfair because these are great, energetic, compelling, witty movies. They’re the ones that still make viewers laugh, and that people still quote over a beer. They’re the best comedies of the aughts.
10. Sideways (2004): Paul Giamatti was born to play sad bastards, but until Sideways, he was mostly doing it under the radar in indies like American Splendor and supporting roles in things like Man on the Moon. It was Alexander Payne’s 2004 road movie about middle-aged adolescents that put him on another level, one that he still wasn’t quite sure how to handle. (As he told the Los Angeles Times when the film began to gain traction, “I hope I strike a blow for chubby bald men everywhere. I hope they rise like an army.”) He’s pitch-perfect as Miles, an aging wine snob who takes his friend, Jack (Thomas Haden Church), on a trip to California wine country to celebrate Jack’s impending nuptials. Jack is a cad and a cheat, and his antics get Miles into hot water a number of times, but the hilarity of their interplay is matched by the fantastic love story Miles finds himself caught up in with Maya (Virginia Madsen), a local waitress he’s adored for years. It’s a comedy about life, and hope, and taking the chance to get what you want. — Daniel Carlson
9. High Fidelity (2000): High Fidelity is a good movie about relationships generally — about the things that attract people to each other, the difficulty in staying together, the alternating pettiness and profundity of love. But since the story is structured around John Cusack’s Rob trying to come to terms with past loves, it’s maybe best described as a break-up movie. And its most valuable piece of break-up wisdom — a moment that briefly stings, and then soothes — comes when Rob is talking to his old flame, Charlie (Catherine Zeta-Jones), after a dinner party. In voice-over, he realizes that “Charlie’s awful. She doesn’t listen to anyone, she says terrible, stupid things, and she apparently has no sense of humor at all.” This is not a universal experience — meeting someone again after a long time apart and loathing them — but the scene concisely speaks to the futility in pining for the past. Odds are, the past has had some work done. Earlier in the movie (and its source, Nick Hornby’s novel), Rob is astonished to find that Charlie is listed in the phone book. She’s become a “myth” in his head, someone who should be living in a distant galaxy, not listed in the White Pages. If you watch High Fidelity in the immediate wake of a break-up, the “Charlie is awful” moment won’t make much of an impression. But if you watch it several years after a break-up, with no need or expectation of relevant resonance, you might just nod along with Rob’s epiphany: that myths aren’t worth the time. — John Williams
8. O Brother, Where Art Thou? (2000): The Coen brothers’ take on The Odyssey is probably their most broadly accessible film to date, thanks to the engaging chemistry between the trio of leads and the fantastic old-time soundtrack full of country music and spirituals produced by T-Bone Burnett. It’s the first of their informal “idiot trilogy” — followed by 2003’s Intolerable Cruelty and 2008’s Burn After Reading, all revolving around gleeful simpletons portrayed by George Clooney — but it’s the best of the lot as well as Clooney’s best performance of the three. He escapes from a chain gang with two other criminals, played by a beatific Tim Blake Nelson and mercurial John Turturro, and sets out across the American South during the Great Depression on a journey to recover more than $1 million that he stashed before being arrested. With nods to everything from Preston Sturges to A.P. Carter, and with a script that revels in the absurd, O Brother is an energetic, warm, character-driven comedy that remains among the Coens’ very best. — Daniel Carlson
7. Kiss Kiss Bang Bang (2005): Great buddy comedies are few and far between, which is one the things that makes Kiss Kiss Bang Bang so good: It’s a fantastic entry in a relatively small field. Writer-director Shane Black, whose screenplay credits include Lethal Weapon, knows what it takes to make a good story that rests on the chemistry between two leads, and his 2005 black comedy neo-noir is a tightly paced flick with machine-gun dialogue and tons of sharp humor. Based in part on the Brett Halliday novel Bodies Are Where You Find Them, the story revolves around Harry (Robert Downey, Jr.), a thief turned actor, who’s flown from New York to L.A. to read for a movie and work with private investigator “Gay” Perry (Val Kilmer). The wrinkles begin when Harry runs into an old high school crush, Harmony (Michelle Monaghan), and tells her he’s a P.I. to get close to her and help her with a case involving her sister, and Perry drags Harry into his own case dealing with a murdered young woman. Black keeps the complicated action flowing, though, never bogging down and always ready with another twist. Harry’s throwback narration is a treat, the dialogue is bristling with energy, and Downey and Kilmer are flawless together. It grossed $4.2 million in the U.S. and was criminally overlooked in a holiday season packed with Harry Potter and the Goblet of Fire and Walk the Line, but that’s all the more reason to seek it out. It’s brilliant comedy that deserves new and longer life. — Daniel Carlson
6. The 40-Year-Old Virgin (2005): There was a time, believe it or not, when Judd Apatow was just a writer and producer with a track record for great but little-seen series like “Freaks and Geeks,” “Undeclared,” and “The Ben Stiller Show.” But in 2005 he released his first film as director, and The 40-Year-Old Virgin would define his style and serve as his calling card. It’s tough to compare it to his follow-up, 2007’s Knocked Up, but Virgin makes the cut as best of the best because of the way Apatow used it to usher in a new era of mainstream American comedy. It plays as a sex comedy for its first half-hour, floating smart jokes that still feel pretty typical of guys trying to get their buddy laid. But the film is so much more than that, and soon enough turns into a hilarious and soul-searching examination of love and intimacy and what it means to be shy, to learn who you are, and to grow up, all embodied in the sweet confusion of Steve Carell. It also put Seth Rogen and Paul Rudd on the fast-track to dominating Hollywood, and they’ve got the best lines in the movie. The film’s gradual change isn’t so much a shift in direction as it is an evolution in the story, and by the time it ends with a daffy but perfect musical number (“Aquarius/Let the Sunshine In”), Apatow’s created the ideal marriage of crudity and heart. — Daniel Carlson
5. Wet Hot American Summer (2002): Written by Michael Showalter and David Wain and directed by Wain, Wet Hot American Summer takes the members of the State comedy troupe that didn’t do “Reno 911!” and creates a fast-paced, wacky homage to the summer camp movies of the 1980s done with a heavy dose of irony. The action takes place on the last day of camp, 1981, and the thin plot splits its time between the attempts of Andy (Showalter) to win the affections of a fellow counselor and a variety of other subplots, most notably the impending crash of a piece of Skylab that can only be stopped by a machine created by the camp nerds and a neighboring scientist played by David Hyde Pierce. But really, the film is a showcase for the sketch-reminiscent humor that’s expertly brought to life by a cast including Michael Ian Black, Paul Rudd, Christopher Meloni, Molly Shannon, Elizabeth Banks, Bradley Cooper, Amy Poehler, Ken Marino, and Joe Lo Truglio. (Meloni’s insane Vietnam vet, the camp chef with bizarre sexual proclivities, is amazing.) The loose collection of scenes are weird and hilarious, from a day-trip to town that feels like deleted scenes from Trainspotting to Showalter’s training montage to become the prototypical cool guy from flicks of the era, right down to the epically cheesy mock-anthem “Higher and Higher.” It’s a smart, sarcastic twist on a special brand of American comedy. — Daniel Carlson
4. Anchorman: The Legend of Ron Burgundy (2004): Full confession: I liked Anchorman enough when I first saw it, but dismissed it as something not worth remembering. In the years since, though, I’ve come to love it and realize just how defining it was for Hollywood comedies in the 2000s. Like a lot of the entries on this list, Anchorman was the first of its little kind, the movie that spawned derivatives that not even its own cast and crew could reproduce. It’s a silly, gleeful skewering of local action news teams as well as sexual politics in the 1970s workplace, but it’s mostly an opportunity for star and co-writer Will Ferrell to do what he does best: create a daffy but likeable character and go to town. It was Ferrell’s second feature script and director Adam McKay’s first film, and that air of freshness, of a willingness to just do whatever comes naturally, infuses the film and keeps it light and breezy. (The spontaneous singing of “Afternoon Delight” is blissful, strangely perfect and always enjoyable.) Paul Rudd, Steve Carell, and David Koechner are fantastic as the supporting team to Ferrell’s blowhard Ron Burgundy, but it’s Ferrell who steals the movie and owns every last absurd, hilarious bit of it. He would go on to play similarly daft characters ruined by their machismo in Talladega Nights: The Ballad of Ricky Bobby, Blades of Glory, and Semi-Pro, but those characters were pale imitations of Ron Burgundy, the lovable idiot who started it all. Anchorman is the smart kind of stupid, and a funny movie made by people at the top of their game. — Daniel Carlson
3. Best in Show (2000): Each successive Christopher Guest movie offers slightly less than the one before it, and none might ever top the quirky joy of 1996’s Waiting for Guffman. But he came awfully close with Best in Show, a hilarious faux-documentary about a group of misfit contestants in a national dog show. The ensemble is packed with members of Guest’s loose troupe: Parker Posey and Michael Hitchcock as an uptight yuppie couple, Eugene Levy and Katherine O’Hara as the geek and the town hussie, Michael McKean and John Michael Higgins as a gleefully over-the-top gay pair, Jennifer Coolidge as a ditz banging an older man, Jane Lynch as a lesbian dog trainer, and Guest himself as the doleful owner of a hounddog. The characters are witty and sharp, and the host of skilled improvisers work together like no other team out there. Fred Willard is flat-out brilliant as the idiotic commentator and co-host of the dog show, and his performance is a mirror of the larger story around him: Silly but sweet, with its heart in the right place. — Daniel Carlson
2. The Royal Tenenbaums (2001): The Royal Tenenbaums is a beautiful, sad portrait of a sprawling family of geniuses in decline, held together primarily by the pain that’s marked the seasons of their ruined lives. The Tenenbaums’ patriarch, Royal (Gene Hackman), is a cantankerous old liar who decides to force himself back into the lives of his estranged wife, Etheline (Anjelica Huston), and three children — Chas (Ben Stiller), Richie (Luke Wilson), and Margot (Gwyneth Paltrow). He feigns cancer in order to move in with the family for a while, but they discover he’s faking it and kick him out, which eventually starts Royal on the road to self-improvement through sacrifice and recovery by helping his family work out their various problems. Royal connects the most with the son he’s emotionally furthest from at the beginning, Chas, whose wife died a year before. … Stiller’s manic energy brings the perfect edge to Chas’ spiraling depression, and at the end of the film, Royal and Chas stumble into a blissful moment of forgiveness as Chas whispers, “I’ve had a pretty bad year, Dad.” And Royal responds, “I know you have,” placing his hand on his son’s shoulder. It’s a calmly magnificent moment. — Daniel Carlson
1. Shaun of the Dead (2004): Shaun of the Dead is one of the rare movies that succeeded in combining two disparate genres, namely, horror and comedy. Lean too far one way, you’ve got a horror movie with comic relief; too far the other, and you’ve got a spoof with no real thrills. But director Edgar Wright, who co-wrote the script with star Simon Pegg, creates a beautiful fusion of the two. The film is genuinely funny, riffing on horror flicks and sending them up a bit (Shaun and Ed’s trial-by-error process learning how to kill zombies is magnificent), but it’s also a full-on thriller. The zombies that overrun London are real, and not all of Shaun’s friends and family survive their gruesome onslaught. Wright, Pegg, Nick Frost, and the rest play the horror and comedy straight, marrying them with moments of genuine emotion, especially when Shaun’s trying to win back his ex-girlfriend and care for his best friend while flesh-eating zombies close in. The jokes are fast and quick, the scares are visceral, and the characters are indelible. It’s just plain wonderful. — Daniel Carlson