10) King of Kong (2007)

Interestingly enough this is not the only documentary on this list. King of Kong tells the remarkably engaging tale of one mans fight against all odds to secure the Donkey Kong record. This epic tale of butt numbing video gamery also has a villain in the scheming, vengeful and painfully awkward Billy Mitchell. This well made doc about an absurd topic just had to squeak onto my list for best comedies of the decade.
9) Black Dynamite (2009)

"CreamCorn you jive mutha!" This film came out of left field and left an instant impact on my mind. Micheal Jai White clearly gets it and thankfully he lets every one else in on the joke. From the absurdity of the beginning to the down right insanity of the end, after 3 recent viewings I still find new things to bust a gut at in this fabulously funny flick.
8) Hamlet 2 (2008)

If 1999 ushered in the new gold standard of comedy musical numbers (South Park: Bigger Longer and Uncut) this brilliant 2008 film made a serious case of it's own. The biggest laughs come in the musical numbers"Rock Me Sexy Jesus" and "Raped In The Face," but the film offers a consistent laugh factor, mostly because of Steve Coogan, one in a long line of British funny men who made a big impact in the 2000's.
7) Forgetting Sarah Marshall (2008)

Judd Apatow's influence on this decade in comedy is as clear as it is huge. He has been the face of a whole new revolution in cinematic comedy, and I will get to his directing work shortly, but of all the films that bear his stamp, Forgetting Sarah Marshall is the best. A film that came out of nowhere it made a star out of Jason Segel, who up to this point was just another face in the Apatow crowd. Add in the lush and beautiful Hawaiian locals and the stupidly gorgeous Kristen Bell and Mila Kunis you have a great comedy that is nice to look at too.
6) O Brother, Where Art Thou? (2000)

It would be a poor comedy list if it didn't include a Cohen Bros. film, and of all their lighter works this decade O Brother is their best. With the basic structure of Homer's The Odyssey and one of the better assembled casts the Cohen's have worked with, this film's journey from Chain Gang to damn bursting is a romp that is every bit as smooth as Clooney's Dapper Daned Hair.
5) Bad Santa (2003)

Billy Bob Thorton made himself a comedy heavyweight with this dirty, raunchy and just plain hilarious Santa heist film. Taking no prisoners, this movie takes every turn for the dark and dirty and just when you think they couldn't go any further, they step it up a notch. Great characters and a smart plot help make this more then just a funny film, it elevates to near classic stand point.
4) The 40 Year-Old Virgin (2005)

As I said earlier Judd Apatow was all over the place this decade in comedies and this is the defacto starting point. This film introduced the mainstream movie audience to a world of comedy that nearly all film comedies have emulated or been a part of ever since. Immediately quotable, terrifyingly relatable, simultaneously sweet and clever, this film, and many subsequent Apatow related films, juggled the whole gamut of emotions and presented them to us in the very best of packages.
3) Clerks 2 (2006)

The clear pinnacle of the View Askew-niverse, Kevin Smith finally made a truly great film. I have always loved his movies, and I even gave serious thought to putting both Zack and Miri and Jay and Silent Bob Strike on this list. Then I thought back on what this film represented and if I was only going to place one Kevin Smith film on the list it had to be this one. Both Smith and his characters are growing and the natural way these people interacted and lived their lives fully fleshed out the set of characters we meet more then a decade earlier. Despite all the sentiment and character work, the film is funny as hell. And as far as swan songs go, Kevin Smith sent his universe out on top.
2) Best In Show (2000)

Christopher Guest was a big part of what made Spinal Tap so hilarious, and then he proved he had comedy chops with Waiting For Guffman, and of all the mockumentaries he has worked on since, none has been as note perfect as Best In Show. Building a stable of actors who keep playing roles in all of his films, Best In Show represented the prefect balance of the wacky and the witty.
1) The Aristocrats (2005)

It surprised me as I built this list, but my top comedies of the decade list begins and ends with documentaries. The very essence of comedy is explored by Penn Jillete and company in this deconstruction of one of the oldest and mailable jokes in the book. Boasting a ridiculous amount talented funny men telling their version of the joke it just builds and builds to the point where I literately was in pain walking out of the movie theater. The reason I put this at number 1 was more then just the side splitting hilarity, but the deep dissecting of what makes a joke funny really makes this film the most interesting gut buster of the 2000s.
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