[tldr_position]Film comedy changed a lot throughout the 2000s. Judd Apatow brought improvisation into mainstream Hollywood movies, which would eventually lead to the downfall of the comedy genre when too many filmmakers lazily used it as a crutch and non-improv-adept actors dragged out scenes, but long before all that, it led to some really hilarious movies. And on top of that, directors like Larry Charles and Christopher Guest were doing their own thing.
There was at least one great comedy in every year of the 2000s, but with the Apatow heyday in full swing and the so-called “bromance” genre on the rise, there were often more than that.
10 Jackass: The Movie (2002)
With franchise cash-ins like Men in Black II and original duds like The Adventures of Pluto Nash, 2002 was a pretty disappointing year to be a comedy fan. But there was one movie that guaranteed plenty of big laughs: the big-screen debut of Jackass.
The stunts pulled in the movie are suitably cinematic, bigger in scale than those found in the TV show, and at a lean 85 minutes (87 if you’re watching the unrated version), there’s very little dead weight.
9 The 40-Year-Old Virgin (2005)
Judd Apatow’s directorial debut, The 40-Year-Old Virgin, changed the film comedy game. By allowing his actors to riff during each scene, Apatow set a record for the most film used for a single production and forever changed the way Hollywood comedies were made — for better or worse.
Apatow’s goal was to take the premise of a raunchy sex comedy and use it to trick viewers into watching a movie that’s much smarter and sweeter than they normally would, and he succeeded pretty admirably.
8 The Hangover (2009)
Todd Phillips’ The Hangover starts off with the kind of premise you can find in any R-rated Hollywood comedy: a bunch of dudes drive up to Vegas for a bachelor party and things take a hilarious turn when the groom goes missing and no one can remember what happened to him.
Thanks to a smartly plotted script that keeps the plot twists coming thick and fast, as well as palpable chemistry shared by Bradley Cooper, Ed Helms, and Zach Galifianakis, The Hangover is a modern comedy classic.
7 Superbad (2007)
Seth Rogen and Evan Goldberg started writing their script for Superbad when they were 13 years old, more than a decade before it actually got made, so it has the distinction of being one of the only comedies about teenagers trying to lose their virginity that was actually written by virgins.
Jonah Hill and Michael Cera have such impeccable on-screen chemistry that they’re genuinely believable as best friends, while the humor holds up surprisingly well.
6 School Of Rock (2003)
Richard Linklater is known for making edgy comedies like Dazed and Confused and sobering naturalistic dramas like Boyhood, so a full-on family film might not sound like it’s in his wheelhouse. But he directed School of Rock and it’s a bona fide masterpiece.
Dewey Finn was the perfect role for Jack Black, making full use of his wholesome presence, physical comedy skills, and musical talents. He develops an on-screen rapport with every kid in his class, all confined within screenwriter Mike White’s airtight plot.
5 Shrek (2001)
While the best cinematic satire of fairy tales will always be The Princess Bride, Shrek is a very close second. Mike Myers, Eddie Murphy, Cameron Diaz, and John Lithgow round out a star-studded voice cast all making icons out of their roles.
Shrek and Donkey’s quest to save Princess Fiona puts a subversive spin on all the usual tropes of fairy tales, while still following a familiar structure.
4 Tropic Thunder (2008)
Since his dad was a movie star, Ben Stiller grew up around actors, and he found that actors who appeared in war movies felt that shooting those movies was their own wartime experience. This provided the seeds of inspiration for what would eventually become Tropic Thunder.
A pitch-perfect satire of the movie industry and a hilarious comedy in its own right, Tropic Thunder is timelessly funny, filled with incredible performances (one of which, by Robert Downey, Jr., was nominated for an Oscar).
3 Best In Show (2000)
Christopher Guest has helmed a ton of hilarious mockumentaries, from Waiting for Guffman to A Mighty Wind, but arguably the pinnacle of the Guest mockumentary oeuvre is Best in Show, satirizing the world of dog shows.
Regular Guest collaborators like Catherine O’Hara, Michael McKean, Eugene Levy (who co-wrote the movie with Guest), and Parker Posey give hysterical improv-heavy performances.
2 Borat (2006)
2006 brought a couple of fantastic comedies, from the absurdist antics of Talladega Nights to the heartfelt humanity of Little Miss Sunshine, but without a doubt, the year’s funniest movie was Borat, which saw Sacha Baron Cohen bringing his Kazakh news reporter character from Da Ali G Show to the big screen.
Watching Cohen dupe unsuspecting interviewees into thinking he’s for real is always a delight, whether he’s destroying an antique shop and trying to reimburse the owner with... inappropriate currency... or bringing a prostitute to a dinner party.
1 Shaun Of The Dead (2004)
There were a lot of great comedies to choose from that came out in 2004: Anchorman, Team America, Sideways — the year brought many hilarious moments from a lot of disparate comic sensibilities. But the year’s best comedy was arguably Edgar Wright’s zom-rom-com Shaun of the Dead.
Combining genre-riffing sight gags with surprisingly relatable human moments and making an on-screen pairing for the ages out of Simon Pegg and Nick Frost, Shaun is a perfect comedy.
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