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

“Good evening, my name is Bill Hicks. I’ve been on the road now doing comedy 12 years, so, uh, bear with me while I plaster on a fake smile and plow through this shit one more time. I’m kinda tired of traveling, kinda tired of doing comedy, kinda tired of staring out at your blank faces looking back at me, wanting me to fill your empty lives with humor you couldn’t possibly think of yourselves.” —Bill Hicks, Dark Poet

Being a funny person on a stage is not easy. It takes a unique determination to stand in front of complete strangers and hope they get it the way you get it. Oftentimes, they simply won’t, but the trick is to keep going. The folks below did, and it is with great pleasure and great awe that we honor them—the 10 best comedians of the decade:

10. Aziz Ansari

With a cultishly popular MTV show (Human Giant), a flourishing stand-up career, a scene-stealing turn in Judd Apatow’s Funny People, and a blog he actually posts on regularly, it’s only fitting that twentysomething comic Aziz Ansari make our list. Whether he’s hanging with idol Kanye West or bloodying up Ted Leo as “Clell Tickle: Indie Marketing Guru,” Ansari stays connected to the music world while taking us all on the highway to the comedy zone. And watch out, entertainment journos; Ansari recently started writing articles for the likes of Interview. Besides, who else can lay claim to literally being the A to Z of comedy? Sara Miller

9. Mitch Hedberg

Mitch Hedberg was a master at relating simple observational ironies to his audience. His stand-up routine could’ve been achingly unfunny in someone else‘s hands, but an atonal, stream-of-consciousness delivery teased an almost confessional humor out of life’s idiosyncrasies. His death from a drug overdose in 2005 only added to his mystique, transforming him into a cult comedy icon. Michael Saba

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8. Eugene Mirman
Eugene Mirman’s dozens of online video clips and his three brilliant standup albums this decade—along with the work of peers like Zach Galifianakis and Patton Oswalt—have taken comedy in a bold new, hilariously absurd direction. Mirman is the undisputed king of the perfectly executed non-sequitur (“This is a bag of dandelions! These aren’t chicken strips at all!”), an expert lampooner of all things pop-cultural (check the Mötley Crüe Behind the Music clip at Eug-Tube), and a master at adapting angry screeds to soulless corporations into stage plays. Plus, he’s a Maxim-magazine-certified “sexpert.” Steve LaBate

7. Ricky Gervais

No one else can pull off the role of the oblivious blowhard like Gervais. The Office showcased his knack for playing a self-important ass, and his brilliant BBC series Extras extracted hilarious performances out of the biggest stars in show business. But the real surprise is how his stand-up comedy sometimes even surpasses his character acting. Emily Riemer

6. Sarah Silverman

Like more than a couple funny people on this list, Silverman specializes in the thorniest of topics—race. The woman who once delivered a bit about Martin Luther King just couldn’t help herself, even in the get-out-the-vote video below, which mixes earnest enthusiasm for Obama with wicked jokes about ethnicity. Nick Marino

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