America's Biggest Loser

Artie lange, the 300-pound, 41-year-old sidekick to Howard Stern, is one of the most complicated, crass and insecure comedians working today — and one of the most successful. He makes a ton of dough: $700,000 per year at Sirius XM and about $3 million a year on the stand-up circuit. Too Fat to Fish, his memoir, is on the New York Times bestseller list. Random House has already signed up his next book for $800,000. There's only one problem: Lange is a carousing, overeating, drugged-up mess who can't handle the mundane details of life, like keeping a girlfriend, cooking, cleaning or even getting an e-mail account. "Every single aspect of my life is totally fucked, other than work," says Lange. "Without my career, you couldn't find a bigger loser."

Lange's persona is a mix of vintage Andrew Dice Clay, obese tragic clown — a niche carved by John Belushi and Chris Farley — and, in the mold of David Sedaris, master anecdotal storyteller of the life of white, blue-collar males. He's good at one-liners — "Crystal meth is a good drug if you need to walk to St. Louis one weekend" is one of his favorites — but most of his humor centers on the difficulty of being a man in America: a greedy, selfish, bottomless pit of need, without a way to communicate with women, who never seem to say what they mean.

Lange overcompensates for his loneliness with drugs, drinking, hookers and gambling, and many of his jokes are about this too. Women are only foils in this drama. "A couple years ago at the Super Bowl in Vegas, my ex-girlfriend Dana wanted to put in a real live bet, in Vegas, with her mother," he says in one bit. "Twenty minutes before the game, I take the Eastern European hooker off my cock, tell her to keep clapping her hands so she doesn't steal anything, and call Dana up. She goes, 'OK, we want $50 on the under. What do you have?' Very calmly, I say, 'I have $50,000 on the over. Good luck to you and your mother.'"

Dana left Lange three and a half years ago — "We broke up because of religious beliefs: She didn't believe I was God" — and he's still heartbroken about it, though it seems like he's much more attached to the idea of her than the reality ("The truth is we were at each other's throats every 10 seconds," he admits). These days, Lange lives alone, in a two-bedroom condo on the Hoboken, New Jersey, riverfront, decorated by his mother. It's a cheerful place, done in an earth-tone style that could be called Crate and Barrel Masculine, with bookshelves stuffed with biographies of his idols, from Chuck Berry to Woody Allen, walls of Al Hirschfeld drawings and an extra bathroom "just for broads." Striped drinking straws are arranged carefully in a jar, and a stack of umbrellas rests by the front door. "My mom has always taken care of me, and now I have a maid that I call my 'Mexican ma,'" he says. "When I lived at home, I never bought shampoo or soap. I just opened the cabinet, and they would be there."