From PEOPLE Magazine Click to enlarge
It might have qualified as a Lost Weekend—only Ben Affleck wasn't losing. After jetting from Los Angeles to Las Vegas on Friday, July 27, Affleck took a seat at the blackjack table in the high rollers' Peacock Lounge at the Hard Rock Hotel and Casino next to his friend Matt Damon. Witnesses say the actor, a Hard Rock regular, wagered up to $60,000 a round—playing three hands at once—while sipping mixed drinks and bottled water. By the time the Pearl Harbor star gathered up his chips in the wee hours of Saturday morning, word had swept the casino that he had won $800,000 and tipped the waitresses and dealers a total of $150,000. After returning to L.A. that afternoon, Affleck mingled with 250 guests at a party—complete with tacos, wings and an open bar—at Mr. Pockets Sports Bar in Manhattan Beach to celebrate a multimedia project produced by LivePlanet, the entertainment company he founded with Damon and two other partners. Later still he had some folks back for an afterparty at his $2.7 million Hollywood Hills home.

Generous? Sure. Extravagant? Perhaps. But tips and party bills were the least of the excesses bothering Affleck when he awoke that Sunday and called a close friend—not to invite him to yet another party but to admit that he needed help. Through a string of contacts, Affleck was put in touch with reformed bad-boy actor Charlie Sheen, who helped to arrange a room for him at Promises, an exclusive drug and alcohol rehab center in Malibu, where Sheen was once a patient. A few hours later Sheen, 35, who has been sober for three years, drove the 29-year-old Affleck to the $33,850-a-month clifftop retreat, where comedian Paula Poundstone is also in residence. "Ben is a self-aware and smart man who has decided that a fuller life awaits him without alcohol," his publicist said in a statement five days later. "He is committed to traveling a healthier road with the support of his family, friends and fans."

With troubled stars like Robert Downey Jr., Matthew Perry and Backstreet Boy A.J. McLean heading into rehab recently, self-destructing celebrities are a familiar Hollywood plotline. But Affleck, with his engaging, unpretentious demeanor and leading-man apprenticeship, seemed to be strolling through stardom. To fans—and even many friends—his admission came as a complete surprise. "I've been out with him a lot, and I've never once seen him get out of control," says Michael Bay, who directed him in this summer's Pearl Harbor and 1998's Armageddon. "I'm hearing he just wants to self-check himself." Indeed, those nearest Affleck understand his reasoning. "He didn't like how he was feeling and saw the signs," says Larry Aaronson, 60, a friend and one of Affleck's former high school teachers back in Cambridge, Mass., who points out that Ben's father, Tim, now 58, is an alcoholic who has been sober for 11 years. "People were telling him, 'Hey, what's going on?' and he said, 'You know what? I think I better go take care of it.' "

Affleck's problem seems less a crash in the fast lane than a sports car stalling on the shoulder. It was only three years ago that he and childhood pal Damon shared the glory of a Best Original Screenplay Oscar for Good Will Hunting, in which they both also starred. Seemingly overnight, a small-time actor who once had trouble paying his $300-a-month rent was stocking his garage with five motorcycles and two Cadillacs, dating It Girl Gwyneth Paltrow and keeping a keg of Guinness stout on tap in the bar of his five-bedroom, 7,500-sq.-ft. bachelor pad.

It was great fun—some of the time. "Ben is doing the best he can to thread his way through the miasmic nightmare of celebrity," his father, now a photographer living in Indio, Calif., told PEOPLE last year. "It's not easy going." Affleck knew it too. "My life changed so much so quickly that I lost any sense of who exactly I was," he told Talk last October. "I made some poor choices."

Yet even that level of self-awareness only went so far. In Montreal earlier this spring, filming The Sum of All Fears, in which he stars as CIA agent Jack Ryan (assuming the role from Harrison Ford), Affleck frequented the downtown strip club Chez Parée. "He was here a few times a week," says the club's manager, adding that he often witnessed Affleck drinking heavily and leaving as late as 3 or 4 a.m. "I think a lot of people were surprised at his behavior." On-set however, Affleck "was nothing but professional," says a source from the movie. "There was a huge crew, and you are bound to hear something, but there was never a negative word."

On a trip to Tokyo in June to promote Pearl Harbor, Affleck spent a couple of nights prowling the clubs in the city's lively Roppongi district. At the Private Eyes strip club he was ushered into a VIP area. But the star seemed to prefer the main floor, where he spent the night "pacing like a caged tiger from stage to stage," says Clare Sale, 21, a model and hostess at the club. "He loved it, walking up and down, showing himself off. By the end of the night he was pretty drunk." At the May press junket for Pearl Harbor, Affleck admitted that he was nauseous with a hangover on the Hawaii set after a birthday party for his actor brother Casey, 26. One high-ranking crew member recalls his publicly snapping at director Bay and often being tired. "He would fall asleep between scenes," says a source. Bay, however, says Affleck "was a trouper" on-set: "You just get tired and burnt out." About once a week he and Affleck, with a small group of cast and crew, would hit Duke's Canoe Club. "We'd hang out and drink some mai tais," says Bay. "But it was nothing excessive."

When he was not working, Affleck's drinking would take place on nights out with actor friends such as Vince Vaughn and Cole Hauser at clubs like Daddy's in Hollywood or in front of the big-screen TV at his L.A. home, which has become a crash pad for friends, including Damon. When visiting his family he could sometimes be found drinking and playing darts at the People's Republik bar in Boston. On a road trip he took for an article in September's Condé Nast Traveler, Affleck tells of heading to a pub in Savannah to meet some locals. "I'm fairly certain I got some great quotes. I mean, I must have, but I don't remember," writes Affleck, noting that he didn't drive home that night. "The next morning, my head throbbing, it was all I could do to find the car."

One place Affleck rarely drank heavily was at the blackjack table. Yet his approach to gambling also seemed to alter during the past year, says one Las Vegas casino source. "He used to be a pretty happy-go-lucky guy," says the source, who has seen him gambling often over the past couple of years. "But his demeanor has changed drastically in the last year, from a guy having lots of fun to, 'This isn't fun anymore.' He'd be serious and stoic, like he's saying, 'I'm here to play and don't talk to me.' "

Whatever the catalyst for his decision, Affleck's family is pleased that he entered rehab sooner rather than later. "Of course, they are concerned," says friend Aaronson, "but they're not hysterical. They've been around this disease a very long time." It wasn't only Tim Affleck's drinking but his gambling that made a mark on Ben's early childhood. "At the end of the football season there would either be tough times or we'd get a VCR," Affleck told Vanity Fair in 1999. Affleck was 12 when his parents—Chris, now 58, a Cambridge elementary school teacher, and Tim, who worked odd jobs as a janitor and mechanic and was active in local theater—divorced. Tim left the family in Cambridge and moved to Indio, where he entered the ABC Recovery Center. Eventually he sobered up and stayed on for eight years as a paid counselor.

Back in Cambridge Affleck spent his teen years pursuing such extracurricular activities as "underage drinking, pot smoking and all the attendant shenanigans," he told Details in 1998. In quieter moments, though, he was busy plotting a path to Hollywood with Damon, his classmate at Cambridge Rindge and Latin High. Affleck made it west first, dropping out of the University of Vermont after one semester in 1990, while Damon continued his studies at Harvard. Small parts in low-budget movies such as 1992's School Ties and 1995's Mallrats finally led to a starring role in 1997's Sundance hit Chasing Amy. And having sold their script for $600,000 in 1994, he and Damon (who had moved west by then) had plenty to keep them occupied--and to look forward to.

When Good Will Hunting opened in December 1997, Affleck's life went into overdrive. Producer Jerry Bruckheimer signed the 6'2" actor for the 1998 blockbuster Armageddon, fashioning the independent-film kid into a screen idol, paying a trainer to work him into shape and a dentist to put caps on his teeth. Affleck bought a loft in Manhattan's TriBeCa and stocked it with his favorite 1980s video-arcade games. He bought his mom a summer home on Cape Cod. With an asking price of $10 million a film, any luxury seemed affordable. "He's having a good time," Affleck's close friend and business partner, producer Chris Moore, said last year. "He bought a nice house, he's got a couple of cars, he's not afraid to take a trip or two on a private jet. He's enjoying himself, and he takes his friends along."

Damon in particular. Though he lives at Affleck's house when in L.A. (he was in residence when Affleck went into rehab and visited him at Promises later that week), Damon calls New York City home and has a quieter approach to fame. "Ben's in the mix, and Matt sits back a bit," their friend, actor and screenwriter Jay Lacopo, said last year. "Matt's wheels are constantly spinning, sizing up a situation, while Ben is participating in it."

For better or for worse. "When you're an outsider in this business and you get your foot in the door, you work as much as you can so they can't dismiss you as a sort of flavor of the month," says Kevin Smith, who directed Affleck in Chasing Amy and this month's Jay and Silent Bob Strike Back. "Ben has run himself ragged jumping from flick to flick." But there were other costs of fame he may not have counted on. "The attention, the lack of privacy, the public ridicule or praise, the amount of options that would come," said his friend Moore. "It's complicated."

By mid-1998 that much was clear to Affleck, who for a time quit drinking altogether. "I started regretting some things I did when I was drunk," he told USA Weekend back then. "It's funny to be obnoxious or out of control, but then it's like, 'I think I hurt that person's feelings. I made a fool of myself' or 'I didn't want to kiss that girl....Now it's kind of depressing to be bombed at 3 in the morning." Affleck has characterized 1999 as a year plagued with unhappiness and insecurity. "I had broken up with Gwyneth, and we'd been together since October of '97," he told Talk. "I felt very adrift....So I thought, 'Okay, I'll go to these parties. I'll try to embrace this life people think I have.'...And I found myself even more miserable."

Though he has been seen stepping out with actress Famke Janssen and Jerry Seinfeld's ex, fashion designer Shoshanna Lonstein, one of Hollywood's most eligible bachelors has remained just that. "The reason I'm single," he told Vanity Fair in 1999, "is because I wouldn't want to be with anybody right now who would be willing to be with me." In last year's Bounce, Affleck plays a hotshot ad executive who gets hooked on booze. But his remark that the role "seems like a natural fit for me" went virtually unnoticed at a press conference. Reporters just wanted to know if he was still secretly dating his costar Paltrow.

For the record, he wasn't. Indeed, it's hard to imagine where Affleck would find the time. Having wrapped The Sum of All Fears—based on Tom Clancy's fifth Jack Ryan novel—in June, he showed up daily through July at the Santa Monica offices of LivePlanet. He played softball in a nearby park with the guys and on July 22 accompanied Damon to Pasadena to promote their LivePlanet project The Runner, a reality-TV series that debuts on ABC in January. On the night before his Las Vegas trip Affleck hung out late with a group of pals at the Lounge, a West Hollywood nightclub. Says one member of his social circle: "He was, as always, drinking."

He won't have that opportunity at Promises, although, along with 12-step sessions and gourmet meals, the facility does offer yoga, swimming and tennis. It also allows its dozen or so patients to take day trips to museums or the movies—which Affleck availed himself of on Sunday, August 5, seeing Planet of the Apes in Marina Del Rey. Director Bay wouldn't be surprised, however, if Affleck opts more often to stay in. "When you go out, and you're always bombarded by people," he says, "at some point you just have to figure out what life is all about."

Anne-Marie O'Neill
Elizabeth Leonard, Michael Fleeman, Julie Jordan, Michelle Caruso, Mark Dagostino and Frank Swertlow in Los Angeles, Tom Duffy in Cambridge, Peter McKillop in Tokyo and Fannie Weinstein in New York City

  • Contributors:
  • Elizabeth Leonard,
  • Michael Fleeman,
  • Julie Jordan,
  • Michelle Caruso,
  • Mark Dagostino,
  • Frank Swertlow,
  • Tom Duffy,
  • Peter McKillop,
  • Fannie Weinstein.