Throughout the 2000s, American film comedy was controlled by a handful of different talent pools. Judd Apatow was producing movies that starred the likes of Seth Rogen, Jonah Hill, Kristen Wiig, and Paul Rudd, who often came up with their own material. Adam McKay was collaborating on a string of delightfully absurdist comedies with Will Ferrell and his various cohorts, from David Koechner to John C. Reilly. Ben Stiller was directing his own starring vehicles with friends like Vince Vaughn and Jack Black playing supporting roles.
All in all, it was a great decade for comedy movies. So, here are the five best and five worst comedies from the 2000s.
Best: The Hangover (2009)
One of the few comedies with a juicy concept that actually makes full use of its premise, The Hangover follows a bachelor party in Las Vegas gone horribly wrong as the groom-to-be goes missing and his friends have no idea where he is.
Bradley Cooper, Ed Helms, and Zach Galifianakis developed a real friendship during the shoot in Nevada, and it shows in their palpable on-screen chemistry.
Worst: Scary Movie 2 (2001)
The decision to make Scary Movie, a Scream spoof, was an odd one because Scream is already a meta deconstruction of the slasher genre, but at the very least, Scary Movie was an enjoyable wacky comedy.
The sequel, however, which attempted to parody everything and the kitchen sink (The Exorcist, The Haunting, The Amityville Horror, Poltergeist, Hannibal — the list goes on), was a bitter disappointment without a single satisfying gag.
Best: Team America: World Police (2004)
Hilariously lampooning Michael Bay’s bombastic actioners through a critique of U.S. foreign policy under the Bush administration, Team America: World Police is a work of satirical genius.
Trey Parker and Matt Stone took an exhaustive break from South Park to make this puppet-infested comedy about an actor who is recruited to infiltrate a terrorist organization. The film wasn’t appreciated in its time, but it’s come to be hailed as one of the greatest cult comedies ever made.
Worst: Grandma’s Boy (2006)
As the story of a dope-smoking video game tester who’s forced to live with his grandmother, Grandma’s Boy has found an audience in unmotivated potheads who feel validated by the lead character. But it’s a seriously lazy comedy.
The film relies on jokes that have been told a ton of times before and were never really funny. Few films can truly pull off gross-out humor, and Grandma's Boy isn't one of them.
Best: Superbad (2007)
Seth Rogen and Evan Goldberg started writing the script for Superbad — which wouldn’t get produced until they were in their twenties — when they were 13. This gives it the distinction of being the only raunchy comedy about teenagers trying to lose their virginity that was actually written by virgins.
The decade-long development of the script made sure that every joke and story beat had been meticulously considered before the cameras started rolling — and it shows in the movie’s tight structure.
Worst: Date Movie (2006)
Throughout the 2000s, Jason Friedberg and Aaron Seltzer came out with a few so-called parodies with the word “Movie” in the title. None of them are particularly good, or even funny, but Date Movie really takes the cake. It’s not just unfunny; it’s painfully so, as it “parodies” gags from more successful comedies by adding several degrees of scatology.
This directing duo has reduced the art of spoofing previously-produced cinematic works, which was pioneered by comic geniuses like Mel Brooks and the Pythons, to lazily cramming in references that are relevant when the script is being written, but are dated by the time the movie hits theaters a couple of years later.
Best: Mean Girls (2004)
Adapted by Tina Fey from the non-fiction book Queen Bees and Wannabes, Mean Girls is one of the few high school comedies to have its feet planted firmly on comedic ground.
As the head writer of SNL, Fey honed her comedy writing to be virtually flawless, and that shows in the airtight structure and countless laugh-out-loud, quotable moments found in Mean Girls.
Worst: The Hottie And The Nottie (2008)
Paris Hilton playing a starring role is usually a sign that a movie is not going to be a notable masterpiece. Anyone who went into The Hottie and the Nottie expecting to see an instant comedy classic was certainly optimistic.
It’s generally accepted that this romcom about a woman agreeing to a date with a man on the condition that he can fix up her unattractive friend is one of the worst movies ever made. Hilton “won” a total of three Razzies for it.
Best: Anchorman: The Legend Of Ron Burgundy (2004)
After honing their shared comedic style on Saturday Night Live, Adam McKay and Will Ferrell brought their distinctively absurdist sensibility to the big screen with Anchorman: The Legend of Ron Burgundy.
Unencumbered by pesky emotional arcs and sporting a rapid-fire joke rate that could rival that of Airplane!, Anchorman is a comedy classic of the highest order.
Worst: Deuce Bigalow: European Gigolo (2005)
Any movie where Rob Schneider has top billing — or any billing at all, really — is probably one you should avoid. Somehow, his 1999 movie Deuce Bigalow: Male Gigolo was popular enough to earn a 2005 sequel called Deuce Bigalow: European Gigolo.
And somehow, that sequel ended up being even worse than the original. Roger Ebert named his book Your Movie Sucks after a quote from his review of Deuce Bigalow: European Gigolo, which led to a public falling-out with Schneider.