The Adventures of NYC's Billionaire PlayboySix-figure booze bashes. Trouble with the law. Sean Parker is the city's Chief Executive Badass.

Photo: Jeff Vespa/WireImage

Sean Parker and fiancée Alexandra Lenas live it up at the Vanity Fair Oscar party in February 2011.

As Hurricane Irene barreled up the East Coast on August 27, more than 100 guests gathered inside a rented mansion in Alpine, New Jersey, for a raucous engagement party. Stone crabs, ice sculptures and cake lollipops topped every table, while indie acts Cold War Kids and Santigold played in the basement.

The biggest storm at the bash, however, was not a hurricane but its host: Sean Parker.

Parker, 31, director of Spotify, founding president of Facebook and a tech titan worth $2.1 billion, was toasting his betrothal to the gamine singer-songwriter Alexandra Lenas. And he was about to live up to his reputation—crystallized by Justin Timberlake in last year's The Social Network—as the most party-hardy geek in town. 

"Eventually there was a mosh pit and all of a sudden I'm standing there with Sean and he goes and gets up on stage and I'm like, no, he's not going to, no, he's not going to…and he jumps!" laughs Parker's close friend and adviser, Eric Lerner, 36. "I and about four other people caught him. He kept doing it, and I'm like, 'No, you do it once!' " 

Ever since Parker set up a part-time home in New York in 2005, the former high school hacker has taken to the city's party scene with a zeal that's left even some of his closest friends agog. Police busts, drug-fueled parties, hugging horses—you name it, Parker's bought the (designer) T-shirt.

"The tech world is littered with guys who are very antisocial," says Shakil Khan, 37, head of special projects at Spotify, the streaming service Parker launched in the U.S. this year. "Sean is very social in a world of antisocials." 

In a series of interviews with Page Six Magazine, Parker's inner circle revealed what drives the bad-boy entrepreneur to succeed and to celebrate—proving that not all wealthy tech dweebs are created equal. Although he once called Facebook's Mark Zuckerberg a roomie, Parker is the opposite of the nerdy, rich-but-thrifty, flip-flop wearing Silicon Valley stereotype. While Zuckerberg rented a modest four-bedroom home in Palo Alto for years, Parker shelled out $20 million for a six-story, five-floor, 8,500-square-foot West Village townhouse last January. He boasts three assistants, a driver and private-jet jaunts. He brags on Facebook about his exploits, like smoking a laced joint with rapper Snoop Dogg during a lavish "Celebration of Music" party the mogul threw in September.

These days, Parker's just as likely to make headlines for his hedonistic adventures as for his business triumphs.

After cofounding the revolutionary music-sharing site Napster, Parker recognized the global potential for Facebook when it was just a student start-up, grooming Zuckerberg as a CEO while securing the funds to put the site on the map. 

Grateful Dead lyricist John Perry Barlow, 64, who befriended Parker during his Napster days, compares the young entrepreneur to the late Apple CEO Steve Jobs. "Sean is really the last interesting person in technology at the moment in terms of really having that kind of Jobs-ian dimension," Barlow says.