"MY NINE LIVES were up a long time ago," says Jay Adams, speaking by phone from the Federal Correctional Institution in Sheridan, Oregon. "God's got different ideas for me than what I've been doing in the past."

It's late May, and the 47-year-old father of modern skateboarding is serving the final months of a reduced four-year sentence for drug dealing. He's been in jail before, and he knows that if he screws up again he'll probably go back for a long time. But he's determined to make his latest fresh start the one that sticks.

"I'm looking forward to being a father to my new daughter," says Adams, whose official public debut will be as a spectator at the X Games, July 31 in Los Angeles. There, he'll be reconnected with fans and supporters he hasn't seen in a while. "I haven't burned many bridges," he says. "I'm pretty sure I have lots of friends waiting with open arms to help me out. At least that's what I'm hoping."

He probably does. Of all the formerly towheaded kids who helped make skateboarding the juggernaut it is today, it was Adams who created the most enduring legend. In the mid-seventies, he was a member of the Zephyr Skate Team, the Santa Monica, California–based crew that included Tony Alva and Stacy Peralta. The Z-Boys popularized Vans and figured out that empty swimming pools can be put to good use when nobody's looking. They invented the moves and, thanks mostly to Adams, originated the anticapitalist vibe that modern skaters like Tony Hawk and Shaun White have harnessed to become multi-millionaires.

"Jay was physically the most brilliant," recalls Zephyr surf-shop co-owner Skip Engblom, now 60. "He didn't have to work at anything."

The group's rise was chronicled in Peralta's 2001 documentary Dogtown and Z-Boys, and Adams emerged as the film's most compelling character, an alienated soul-roller who seemed to be above the crassest forms of cashing in. Whether it was true or not—Adams says the film oversold the extent to which he walked away from skating and surfing—a star was born. Adams went from being another bad boy on wheels to a tragic hero.

And for a while, Dogtown's success put its three stars back at the top of skating, too. Peralta sold a screenplay that became 2005's Lords of Dogtown, starring Emile Hirsch as Adams; Alva revived his skateboard brand in Los Angeles; and Adams signed fresh sponsorship deals. "I was doing pretty well," he says. "Then I fell back into my old habits. It snowballed into a complete relapse. I was fooling everybody—well, not everybody."

In November 2005, Adams was arrested at the home he shared with his pregnant wife, Alisha, on the North Shore of Oahu. Already on parole for an earlier offense, he'd been recorded on a June 2004 federal wiretap introducing a crystal-meth dealer in California to a buyer in Hawaii.

Adams's history of legal problems and drug abuse dates back to his Dogtown days. While Alva and Peralta chased careers and became prototypes for today's skating professionals, Adams fell in with the violent subculture of L.A.'s punk scene. "He hung out with guys that were older," says Alva, now 50. "They were pushing him to do things that he wouldn't have done if he wasn't trying to gain acceptance."

After a Suicidal Tendencies concert in 1982, Adams taunted a gay couple outside a popular Hollywood hangout. When one of them yelled back, he knocked him down. Adams says he fled but that the crowd behind him closed in and kicked and beat the men, killing one of them. He was convicted of felony assault and sentenced to six months. Then, in the mid-nineties, his mother, father, grandmother, and brother all died within a span of a year and a half. "After that, I started using hard," he says. "I tried needles for the first time. It was my way of not dealing with the grief."

When Dogtown and Z-Boys debuted, Adams was doing two and a half years in a Hawaiian jail for a drug offense. After his 2002 release, he parlayed fame from the documentary into a fan base of skating nostalgics. Engblom says people related to him as a symbol in "some beautiful loser category." Adams signed endorsement deals indiscriminately, sometimes with competing companies for the same product. He also neglected to pay his taxes.

Now, after three years of incarceration, Adams is getting another chance. At press time, he was scheduled for a July 7 early release to a halfway house in Southern California, where he'll be able to help raise his two-year-old daughter, Venice. (He also has a son, Seven, who's 14.) Adams will return to skating, but not as a pro. Under the terms of his release, he'll manage the skate park at the Costa Mesa headquarters of the surfwear company Hurley. His duties there will include maintaining order and cleanliness. Adams's friends say it's exactly what he needs.

"When he doesn't have a routine, the old ghosts return," says Peter Townend, 55, a Huntington Beach–based action-sports agent and former world surfing champion who's known Adams for four decades. "If people pay him to be Jay Adams, he'll just get in trouble again."

Engblom, who now owns Santa Monica Airlines Skateboards and considers Adams a friend, describes a pattern of self-destruction that he hopes will end. "It's like: Get something going, be on the verge of big success ... and then crash and burn."

By all accounts, Adams had begun to straighten up in the 18 months between the wiretap and his 2005 arrest. He'd kicked heroin, started going to church again, and gotten married and started a new family. When the time came for his sentencing, in April 2007, the judge took notice and gave him leniency for his effort to put his life back together.

At this point, it's up to Adams to pull off a trick that he was always able to do effortlessly on a skateboard: a 180.