Entertainment

The Twenty Sexiest Ugly People

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Beauty maybe, but sexiness is definitely in the eye of the beholder. And while beautiful people get sexiness for free (usually, anyway — check back soon for some exceptions), ugly people have to work for it. If you're plump, craggy, acne-scarred and irresistable, you've earned the hearts fluttering in your wake. We've laboriously assembled this list of definitively ugly people (physically ugly, anyway — they're beautiful on the inside, we're sure), and we're telling you we want to sample their goods. We're admitting that, look, the following people are not pretty, but that wouldn't stop us.

We're going out on a limb here, people. Here are the twenty sexiest ugly people alive.

20) Daisy De La Hoya
We cannot even begin to account for Daisy De La Hoya. She's like the bastard child of Marshall McLuhan and Rube Goldberg. When we try to observe Daisy like you would a normal person, all we see is a blur of colors and that bottle of whiskey she seems to always have nearby. Did you see that episode where the guy broke a glass over his own head? Daisy exists in a world of cognitive dissonance, which makes her the perfect choice for a list like this one. — Joe Bernardi

19) Danny McBride
Don't judge Danny McBride. Sure, his redneck pompadour and puggish face may suggest the fattest, laziest fuck south of Raleigh-Durham, but tell your instincts to shut the hell up and assess the comedian for his whole: a sebaceous tower of Dixie-fried virility. Whether playing a sad-sack sensei in The Foot Fist Way or the John Rocker-esque Kenny Powers in Eastbound & Down, McBride brings a good ol' boy sensuality to his craft. We bet his pheromones smell like Schlitz and coleslaw. — Cyriaque Lamar

18) Amanda Lepore
A lilting, strutting hybrid of Warhol's "Marilyn" and Picasso's La Lecture (Woman Reading), New York City's transsexual empress has stretched both the boundaries of gender and her own epidermis, thanks to oodles of elective surgeries. Nothing like Madame Lepore exists in nature, so it's inevitable to think of her as a nigh-mythic creature, or some kind of freaky Plasticine wet dream. — C.L.

17) Marilyn Manson
Say what you will about Brian Warner's satanic kabuki act. Ever notice that the man has a nonstop queue of alt-nubile tail parading through his bedchamber? Rose McGowan? Dita Von Teese? Evan Rachel Wood? Lord below. That's a pretty lively roster for a guy who once admitted, "I'm death on wheels, the way I look." Yes, Marilyn, death on wheels. Like a Ford Pinto, with a velour-lined hatchback. Mmm, devilish. — C.L.

16) Amy Winehouse
Her undeniable talent helps mitigate her looks, sure, but more importantly, Amy Winehouse owns being a strung-out mess in a way nobody else has since the '70s. With her labyrinth of hair, naked-girl tattoos and extremely public substance-abuse problem, she looks and acts the way the media wishes every star looked and acted. Not everyone can do it with this much poise, though, and when she's on stage, all the drug problems in the world pale in comparison. — J.B.


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15) Biz Markie
Consider the dualism of hip-hop's Clown Prince. On one hand, he's the MC who penned "Pickin' Boogers," he's so wide he can scratch vinyl with his waistline and his brainpan is the size of a small asteroid. On the other, he's the sensitive soul who warbled "Just a Friend," kids love him (see his Yo Gabba Gabba spots) and he's such an ill beatboxer he'll serenade you with an entire philharmonic. If the Biz ain't Prince Charming material, then we don't know who is. — C.L.

14) Ric Ocasek
The late '70s and early '80s were a golden age for unphotogenic frontmen. (See Perry, Steve.) But even in those heady times, Ric Ocasek's bird-head still managed to stick out above the crowd. We can stand here all day freaking out about Ocasek's alien bone structure, or we can listen to "Moving in Stereo" and start in with the heavy breathing. Paulina Porizkova apparently went with the latter; points to Ocasek. — J.B.

13) Danny Trejo
Trejo is not a man. He's a living piece of igneous rock that's spent years out on a windy plain somewhere in the middle of nowhere, heavily bombarded by meteorites and tattoo artists. The man's built an entire career out of looking like a cliff face. Don't pretend you wouldn't take that plunge. — John Constantine

12) John C. Reilly
His face is made of worn Naugahyde. He's got the most egregious white-person afro since Bob Ross. And his voice is the mating call of an elephant seal. But that dumb-puppy-dog look belies an animal lust; you get the feeling he might leap a table and suddenly start making out with you. Lip-to-lip with this shaved-Chewbacca of a man, you'd know the meaning of desire. — C.L.

11) Woody Allen
There must've been something awfully appealing about Woody Allen for him to pull babes like Diane Keaton and Mia Farrow. He might be short, balding and bespectacled, but Allen makes his neuroses work for him. And if the awkward nice-guy routine doesn't fly, he's got a secret weapon: underneath that veneer lies a voracious sexual appetite that cannot be satisfied by time or starlets. — J.B.


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10) Howard Stern
Howard Stern, despite looking like an underfed version of the creature from the black lagoon, can clearly pull (please note wife Beth Ostrosky). Women say they want confidence, and he's clearly not afraid to ask politicians about their affairs or the world's most beautiful women what gets them off. Just goes to show that a little chutzpah, a razor wit — and tens of millions — can make up for oiled-chainmail hair and the Adam's apple of Ichabod Crane. — Jack Murnighan

9) Willem Dafoe
An immortal Simpsons episode finds Bart and Lisa watching a movie called "The Muppets Go Medieval"; they ask their father why one of the muppets is made of leather, not realizing they're looking at an aging Troy McClure. We ask the same question every time Willem Dafoe is in a movie. The guy looks like a hairless Shar-Pei, and he only gets scarier when he smiles or grimaces. It's a little exciting to be scared, isn't it? For a taste of Dafoe's strange allure, forget his crazy/sexy Jesus in The Last Temptation of Christ and go straight to his drag-queen performance in Boondock Saints. — J.C.

8) Steve Buscemi
In his novella The Shadow Over Innsmouth, H.P. Lovecraft described "the Innsmouth look," a mien you inherit if your pop was a horny deckhand and your mom was an immortal fish-monster. At the risk of sounding crass, we'd marry indie cinema's ultimate character actor in a heartbeat, even if meant wall-eyed tadpoles nine months later. Enid from Ghost World had the right idea. — C.L.

7) Tilda Swinton
It's appropriate that Tilda Swinton played the White Witch in The Lion, The Witch, and The Wardrobe — she looks like she could turn you to stone with a glance. But even if a David Bowie cloning experiment went awry here, some of that cold allure came through. She may not be pretty, but Tilda Swinton is damn fierce. — J.C.

6) Iggy Pop
Perceptive readers may remember that Iggy ranked #9 on our list of the forty sexiest frontmen in rock history. That his sinewy ass should also end up here is damn impressive. The years since Raw Power and Lust for Life have been hard on the man's face, what with that heroin habit and those cameos on The Adventures of Pete and Pete; the fresh-faced Michigander who barked "TV Eye" now has the desiccated matte of a peat-bog mummy. But when it comes to sixty-two-year-olds who could still nail the shit out of you, the former Mr. Osterberg is hard to beat. — C.L.


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I Did It for Science: Topless in Central Park

5) Paul Giamatti
Paul Giamatti does many things well. He does schlubby (American Splendor). He does regal (John Adams). He even does a sterling "oh-my-God-I'm-so-fucking-histrionic-because-I'm-surrounded-by-total-dross" (most of his lesser films). But does he do handsome? Nuh-uh. Somebody's got to say no to firm jaw lines and six-pack abs, and no one does it with Giamatti's panache. His imperviousness to good looks is, in turn, incredibly sexy. — C.L.

4) Courtney Love
Mrs. Cobain could be a fetching lass if she cleaned up a bit, right? Wrong. Go watch The People vs. Larry Flynt again. Courtney Love is ugly. While we're back in the mid-'90s though, re-watch Love's drunken ambush of Kurt Loder and Madonna at the 1995 MTV Video Awards. Fucking with Madonna is sexy enough, but this singular moment in time also reveals Courtney's magnetism. Yeah, she's the girl your friends tell you not to go home with when you've had a few. But she's also the gal you go home with after telling your friends, "I'm not even drunk." — J.C.

3) Mickey Rourke
Since The Wrestler, no one can mention Mickey without talking about his puffy, almost feline face. The result of botched reconstructive surgery following an ill-advised pro-boxing career, Rourke's mug is a far cry from the days of The Pope of Greenwich Village. That said, he's a convincing and affable tough guy, but he also comes off like a delicate, attentive lover. You can just picture those meathook-hands wrapping around your lower back and carrying you somewhere you desperately want to be. — J.B.

2) Sandra Bernhard
Sandra Bernhard could probably beat up any of the other people on this list. After a multi-decade career of running her mouth, and extending gaping gap-toothed sneers to anyone who got in her way, Bernhard has emerged as a sort of sex symbol for contrarians, posing for Playboy and playing one of television's first open lesbians along the way. She's definitely funny-looking, but she's a bad-ass kind of funny-looking. Like a hammerhead shark, or a VW Bus. — J.B.

1) Keith Richards
He may have been at war with his own body for four decades straight, but there's always been a handsome glint in Keith Richards' eye that suggests he thinks being a rock star is as strange and funny as we all hope it is. That glint, combined with being one of the only people on earth allowed to tell Mick Jagger to fuck off, creates a sexiness that transcends things like "a terrifying, masklike face." It's true that Richards might be better-looking these days if he'd stayed on the straight and narrow, but then he wouldn't be Keith Richards. — J.B.


The 20 Unsexiest Beautiful People
The Top 43 Sexiest US Presidents
I Did It for Science: Topless in Central Park