25 Funniest People in America

Presenting The 25 Funniest People in America. From Conan O’Brien to Stephen Colbert, Tina Fey to Craig Ferguson, let’s count down the names of the entertainers who make us laugh the hardest.

25. AUGUSTEN BURROUGHS

Burroughs’ best-selling memoir Running with Scissors — about being raised by a nutso shrink who studies his poo and rents the back shed to a pedophile — is unbelievably disturbing. And sidesplitting. At first we felt guilty giggling at his adventures with an electroshock therapy machine, but Burroughs knows that laughter is the best antidepressant. Much better than booze, which the author struggles to kick in his equally effervescent follow-up, Dry.

24. CATHERINE O’HARA

After her run on SCTV in the late ’70s, Hollywood didn’t know what to do with O’Hara. Fortunately, Christopher Guest did. In Waiting for Guffman, she and Fred Willard are tracksuit-wearing answers to Ginger Rogers and Fred Astaire; in Best in Show, she’s a onetime floozy with a prize terrier and a torrid past; and in A Mighty Wind, O’Hara shows off a subtler comic touch, proving that humor doesn’t always mean a pie in the face.

23. SARAH SILVERMAN

The Lenny Bruce of the 21st century might be this hot, foul-mouthed, button-punching stand-up. Silverman is ruthlessly funny about topics like sex, the Holocaust, and 9/11, which may be why The Sarah Silverman Program has a permanent slot on our DVR. Oh, and if you hadn’t heard, she’s f—ing Matt Damon.

22. DAVE CHAPPELLE

The fact that Diamond Dave is all but absent from the comedic stage these days doesn’t invalidate his funny. After all, Chappelle’s revered Comedy Central show — on which the wiry comic gleefully engaged in crass T&A humor, swore like a sailor, and mocked everyone in the multiculti rainbow, confronting race in a way that is positively Pryor-esque — is still the best sketch comedy this country has seen in more than a decade. For that alone, he deserves a spot on any list like this.

21. DEMETRI MARTIN

You know what’s funny? Palindromes and anagrams. ”Shut up, Grandma,” you say, but we say shut up yourself and watch Demetri Martin work a stand-up mic. ”A drunk driver’s very dangerous. Everybody knows that. But so is a drunk backseat driver — if he’s persuasive.” The floppy-haired heir to Steven Wright won a prestigious award at last year’s Edinburgh Festival Fringe, taking him from the comedy underground to…the comedy slightly less underground.

20. DIABLO CODY

Not to be partial, but the newly minted Oscar winner showed off her comedic — and emotional — chops with her debut screenplay for Juno. Did we mention it won an Oscar?

19. CRAIG FERGUSON

Late night is the province of the mono-name. Jay! Dave! Conan! Then there’s that Scottish guy, two-name ID required: Craig Ferguson. You know, the one who can’t quite be pinned down. Since taking over CBS’ Late Late Show from Craig Kilborn in 2005, Ferguson has brought a fresh burst of energy to the format. He’s reinvented the opening monologue, doing away with most of the topical jokes and just ad-libbing about his life. Along with fresh energy, he’s brought something else — ratings. Ferguson, 45 and a brand-spanking-new U.S. Citizen, doesn’t get as much media attention as time-slot competitors Jimmy Kimmel or Conan, but with an audience of just under 2 million, the great Scot outperforms the former and has climbed within 500,000 viewers of the latter.

18. JACK BLACK

Black is an entirely new classification of human: the frenetic slacker. Before his turn as doofus band reject/inspirational teacher Dewey Finn in School of Rock, he was the Ritalin-deprived half of Tenacious D (along with his partner, Kyle Gass) and the list-obsessed record-shop shlub in High Fidelity. He is, inarguably, the coolest fusion of music and comedy since Spinal Tap. (And, if Tropic Thunder is as good as we’ve been led to believe, we’ll forgive him that whole Nacho Libre business.)

17. DAVID LETTERMAN

With a receding hairline and a jogger’s grim jowls, Dave is no one’s idea of a hip comic, and he likes it that way. New-school gone old-school, the upstart who first pumped irony into the talk show still rails against the stupidity of the powerful and yet has the charm to melt Julia Roberts.

16. AMY SEDARIS AND DAVID SEDARIS

Big brother is the best-selling author of the sublime autobiographical essay collections Me Talk Pretty One Day and Naked, full of terrific riffs about stuff like his cuckoo-clock North Carolina clan and his midget guitar teacher. Little sis was the rubber-faced star of Comedy Central’s truly strange Strangers With Candy, as well as coauthor of the book Wigfield.

15. WILL FERRELL

See, there’s this man-child who latches onto Will Ferrell in most every role he plays — and good luck getting the little guy to let go. As a result, we are treated to inspired displays of dolt-trapped-in-the-headlights hijinks, be it in the form of Old School’s keghead Frank the Tank (who goes from repressed to regressed to undressed) or Talladega Nights’ Ricky Bobby, the dumbest, most earnest NASCAR driver on the circuit — who’s also the most comfortable with his sexuality.

14. RICKY GERVAIS

Okay, so he doesn’t spend all that much of his time in America. We don’t care. Whether as the creator of The Office and Extras, a supporting actor in movies like For Your Consideration or Night at the Museum, or doing killer stand-up (as seen most recently in Grand Theft Auto IV), he’s still as funny as the dog’s bollocks.

13. ELLEN DEGENERES

DeGeneres, whose career seemed all but kaput a few years ago, has earned back adoration simply by being her affably dry self on the Emmy-winning The Ellen DeGeneres Show. Whether it’s her circuitous monologues, her deadpan celebrity interviews, or that vocal turn as Dory in Finding Nemo, she remains one of the cleanest, coolest funny ladies around.

12. DAVID CROSS

All conversations about his genius start here: Along with Bob Odenkirk, he created the cunning HBO sketch series Mr. Show, which routinely put SNL to silly shame. And not only does Cross work little miracles in supporting roles (remember his role as feckless freak-job Tobias on Fox’s Arrested Development?), he can drop some pretty fearsome stand-up (who else talks about being raped by the Virgin Mary?). Simply put, this dude never kowtows for his funny.

11. CONAN O’BRIEN

Smarty-pants isn’t usually a compliment, but O’Brien wears them so well. When this Harvard geek isn’t riffing on Muammar Gaddafi in his monologue, he’s making absurd innovations in low-brow comedy. Now, let’s see if those absurd innovations will play on The Tonight Show….

The Top 10 are after the jump!!