The 10 Best Comedians of the Decade (2000-2009)

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5. David Cross

David Cross  is alternative comedy‘s renaissance man. He cut his teeth on HBO’s wildly subversive Mr. Show with co-creator Bob Odenkirk, a fellow traveler in L.A.‘s mid-nineties standup circuit. Cross spent the next decade and a half headlining tents at festivals and appearing in music videos with Yo La Tengo and the New Pornographers, becoming indie-dom’s patron saint of irony. He’s played cultural critic, antagonist and slaughterer of sacred cows on two stand-up albums to date (released on Sub Pop, natch), the first of which earned a Grammy nod. And in 2003, he pulled his analrapist stocking over his head for a turn as Tobias Fünke in the now-legendary Arrested Development. Michael Saba


4. Chris Rock

Although he first hit it big in the ‘90s, Rock became comedy royalty in the 2000s. While he was making fluffy, mainstream films like Madagascar, he never shied away from edgy comedy, and his HBO specials and stand-up appearances from the 2000s are among his best, sharply skewering black culture, politics and even Oprah. Emily Riemer


3. Patton Oswalt

I’m not a big fan of stand-up comedy, but the first time I heard a Patton Oswalt bit I immediately felt a deep, emotional bond with that round little man. His rant about KFC’s Famous Bowls—which I’d lamented over with friends but never so eloquently as his definition: “a failure pile in a sadness bowl”—has become kind of an annoying Thing (even to him, I think—when I saw him in February, he chastised a guy for requesting it between jokes), but it perfectly encapsulates what I love about him. Oswalt has this deep sense of cultural shame that radiates outward but also pierces deep into his own psyche—he knows how ridiculous everything is, but knows, too, he’s no better than anyone else. He’s funnier than just about everyone else, though, so that helps a lot. Rachael Maddux


2. Zach Galifianakis

In 2008, we described Zach Galifianakis’ act thusly: “a mix of the hyper-intelligent and the low-brow—blink-and-you’ll-miss-them absurdist nuggets. Sometimes the joke is simply the mispronunciation of a word, other times it’s in pushing a button that’s particularly taboo with his audience.” Since then, the dude’s blown up a little bit, starring in blockbuster movies (The Hangover) and critically acclaimed television (HBO’s Bored to Death), while having many an awkward moment on his web series, Between Two Ferns. Did we mention he’s got a beard that just won’t quit? Catch him live if and when you can. Austin L. Ray


1. Dave Chappelle

The funniest man of the decade spent some well-documented time off the grid, then emerged from seclusion to assure everyone that he wasn’t crazy, a crackhead or a crazy crackhead. It’s no wonder speculation was so intense: When he stepped into the spotlight—whether on his side-splitting Comedy Central show or in a stand-up setting—Dave Chappelle was supernaturally magnetic. You couldn’t take your eyes off him, couldn’t stop laughing, and couldn’t help yourself from watching to see which taboo he’d skewer next. Race was his specialty, as evidenced in the clip below, which contains his immortal “Terrorists do not take black hostages” bit. Nick Marino

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