AMERICA'S BIGGEST LOSER

He is one of the funniest stand-up comedians in the country -- a multimillionaire with a bestselling memoir, hordes of fans and even the occasional groupie. So why can't ARTIE LANGE stop trying to kill himself?

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 ajar, 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."

These days it's just him, his mother and his sister -- his father, a TV-antenna installer from Newark, New Jersey, fell off a ladder on the job in 1985, when Lange was in his first year of college. His dad was his best friend and hero, and Lange used to work for him during the summers, holding the ladder as he climbed on roofs "like Superman," says Lange. Artie Lange Sr. was a quadriplegic until he died four and a half years later from "losing the will to live," says Lange, cryptically. This would seem to be the key to Lange's personality: the blow of losing an idealized father who looms ever more heroic in one's mind, the battle to measure up to him lost for eternity. "That's part of it," says Lange. "But that pain is long over. There's got to be something else."

WHAT'S WRONG WITH Artie Lange is the kind of million-dollar question that no one has satisfactorily answered, so it's best to ditch it and just look at the particulars. He has been on and off of heroin for three years. In fact, he was on a five-day bender during the photo shoot for this article, before Christmas. Our photographer was in his living room, and Lange was hiding in the bathroom, snorting a dime bag. He gets into drugs like this every couple of months, before trying to go straight again. Then he gobbles the opiate-blocker Subutex to ward off withdrawal, or he downs a whopping 20-odd painkillers like Vicodin and Percocet per day, or he dries out in rehab centers of various disciplinary ideologies.

This time, Lange got shipped off to a detox center in Florida for a 21-day program of cucumber juice, therapy and wheatgrass enemas. "I had to get a doctor's prescription for an apple, because apples have too much sugar," he says. Seven days later, he was ready to split: A weed-smoking, Neil Young-loving chick from Pittsburgh with whom he once had a fling was on vacation in Miami, and he wanted to get into her pants. He ditched the detox center and booked a room at the Setai hotel in Miami's South Beach for $1,800 a night. He took that woman to a $300 dinner at an Italian restaurant, and the next night he treated another lady to a $750 meal at Nobu. He spent $120 on a haircut and $1,800 on two pairs of sunglasses. Then he started to think that it would be good to make back all the money he'd just wasted, so he booked three shows for later in the week at Caroline's comedy club in Manhattan for $35,000. The whole rehab thing was expensive, costing him about $17,000. Checking out early, he reasoned, didn't leave him a penny poorer. Plus, he didn't want to postpone the interview with ROLLING STONE any longer. He's always afraid that everyone secretly hates him, that everything he's worked for is going to be suddenly snatched away.

So here he is, on January 7th, back in New York on The Howard Stern Show two weeks earlier than planned, and his mother and sister are furious. Even Stern is upset. Lange sweats into the microphone, his new $900 sunglasses clapped on his face; at least he's not nodding off today, which has been known to happen. The rest of the staff bust his balls: "Artie wouldn't stay in rehab, he had to go-go-go," chimes in a producer, to the tune of Amy Winehouse's "Rehab."

"I've never heard of someone kicking drugs with wheatgrass enemas," declares Stern co-host Robin Quivers. "There are a lot of layers Artie needs to confront."

"Are we retarded to have thought you were falling asleep on the show because you ate too many cupcakes?" yelps Stern producer Gary Dell'Abate.

Lange promises that he's ready to stay straight. He wants Stern to drug-test him ("It's a daddy complex!" exclaims Quivers). Stern parries: 'You don't have to lie to me, Artie," he says. 'You can tell me when you're on heroin, because I don't care." But Lange keeps pressing the point. Peering through his lightly tinted glasses, with a lot of mischief but also genuine sadness in his watery blue eyes, Stern shakes his head. "It's a saga," he says. "Artie is involved in a saga."

In his foreword to Lange's book, Stern puts it another way. "He's fucked up!" he writes. "That's it. He's fucked up. He's just like us, only 10 million times worse."

HERE ARE THE WAYS THAT Lange is fucked up: He can't get into a relationship that lasts longer than six months. He likes to blame other people for his problems. He lies a lot. He eats a lot. His chin and cheeks are swollen from eating too much, giving his face the look of a pear. He ate a whole pizza the other night, just having the blues. He is uncouth and thin-skinned. He will do anything for a laugh. When he was younger and pulling goofs to get girls' attention, he once slipped a robbery note to a cute bank teller, in an hommage to Woody Allen's Take the Money and Run, resulting in one of his many arrests.

As in every good Italian family, Lange's mother is a saint, and his father was a scoundrel. On the day Junior was born, the elder Lange was on trial for keeping $200,000 in counterfeit bills at their house in Union, New Jersey, for a loan shark. "In my neighborhood, we were always taught that the mob didn't exist, but if they did, they were very nice people," says Lange. After his dad fell, Lange tried to be the man of the house losing his virginity to a Brazilian hooker in the back seat of his dad's handicap van was the first step. He took a job as a longshoreman at Port Newark, where he unloaded orange-juice concentrate from South America between meatball breakfasts and visits to his bookie. At 24, he quit the union to pursue his dream of becoming a comedian, working as a cabdriver for cash. When he booked sets in Manhattan, he'd double-park his taxi in front of the club, run in for 20 minutes, then clock back into the job.

In 1995, after only three years on the stand-up circuit, Lange caught his break: He was cast as an original member of MADtv, the Fox sketch-comedy show. He moved to Los Angeles. For whatever reason -- again, we could speculate on his deep need to screw up -- he developed an addiction to cocaine, even drinking it in glasses of Jack Daniels when his nose became too sore for another line. At 28, he tried to commit suicide with pills and whiskey. "I was 100 percent serious about dying," he explains.

Lange didn't take rehab seriously -- he paid off the director of the center to write him a note saying that he was able to take a role in the film Dirty Work -- but Chris Farley's death, from booze and speedballs, shook him to the core. "I'd just been with him, and I'd even tried to bang the same hooker that he had -- just so I could say I'd done it," says Lange. "I couldn't believe he died." He went straight for a while, until he began to feel lonely when he did standup. He started to take prescription pills to fill the void. "When I'm on the road, there's always some kid in the audience selling Percocet or Vicodin," says Lange. One night, a dealer gave him some advice. "All that Vicodin is bad for your liver," he told Lange. "Take heroin, man. It's better for your liver."

There's not much that's funny about Lange's heroin addiction, and even he doesn't seem to have a new joke about it. It's brought a fresh roster of shady characters into his life, like a drug-dealing ex-stripper from New Rochelle, New York, with whom he's having a fling. She shot him up in his sleep last year (Lange usually snorts the drug). "She said, 'It's just skin-popping, I didn't tie you,'" he says. "It was 12 hours of euphoria." Then there's the doctor whom Lange pays $1,000 a visit, for the comfort of knowing that he won't leak to the tabloids. A house call is extra dough, as he found out when he missed a Comedy Central roast for Bob Saget this summer, after a binge. "My agent called me and said, 'Comedy Central says you have to come to this thing,'" he says. " "They'll get you an ambulance to take you to a private plane at Teterboro, a private doctor on the jet, and if you still can't do the show when you get to L.A., they'll eat the $65,000 in costs.' " Lange turned them down. "I was like, 'I know these kinds of doctors -- if I beg him to shoot me up with morphine, he's going to do it to keep Comedy Central happy. And I'll have a heart attack over Missouri.'"

That's the way it's been this year: Lange's missed a lot of his commitments. Backstage at his stand-up gig at Caroline's a day after he reappeared at the Stern show, he seems uncomfortable, as a friend -- who is wearing a shirt that says AMSTERDAM -- brings up all the fun stuff that he didn't make it to this year: the Bruce Springsteen concerts, the bachelor parties, the sports games. Lange interjects, reminding him that there's one thing he didn't miss: the weeklong tour he did for the troops in Afghanistan. "I had to do that," he says firmly. "I would have killed myself if I let down the USO."

SO IS LANGE GOING TO MAKE it? Some days his spirits are down, like they were after his show at Caroline's. Two blondes from Long Island sitting in the front row had even thrown themselves at him, and he barely got excited about it. "I'm over drunk chicks," he says, though he palms their numbers for future use. That night, he stays up until 6 a.m. watching a documentary about Charlie Parker, whom he idolizes, and not for his music. He gets to thinking about a girl he likes in Seattle. "She texted me, and I really got depressed," he says. "Why can't I be with that girl? I would rather be a plumber with her in Seattle than have this gig."

Other times, Lange seems to be doing all right, particularly when there's tomfoolery to be had. He's great fun to be with in the car, zipping through New Jersey in his silver Mercedes. No one's allowed to wear a seat belt. "I don't play that shit," he says. "That's un-American." He blasts through a couple of stop signs and floors it to the Holland Tunnel, pulling into the E-Z Pass lane. "I think I figured out a scam," he says excitedly. "I've been blowing through E-Z Pass all year without paying!" He talks about his car. "I remember when I got my first Mercedes in Los Angeles, and I thought I was a big deal because I had a 500 CL, you know, I got somewhere in life," he says. "And some kid was like, 'Hey, I'm thinking of getting this car too, do you like it?' And I was like, Yeah, I like it. I like blow jobs too.' Then the kid always sucks my dick. It's great."

On 50th Street in Manhattan, he pulls over to do an errand, leaving me in the car. A cop immediately starts to write a ticket, so I repark down the street. "You didn't have to do that," Lange says, huffing and puffing as he runs up behind. "You could've just told them you were with Stern and Artie." He cackles manically. "I can get away with anything."