Then, suddenly, he was dead at 41 - the cause still a mystery three weeks later.
Friends attended a memorial Saturday night at the Theater for the New City in Manhattan's East Village. With Chamberlain's body in a Manhattan morgue, a rose-filled casket on a makeshift altar was to hold objects reflecting a life both thrilling and sad.
The casket and its contents are to be burned in effigy this month at the Burning Man arts festival in Nevada's Black Rock Desert, where Chamberlain's ashes are to be scattered. For the festival, he recently helped create a mammoth metal sculpture featuring parts of 18-wheelers.
Chamberlain is believed to have died July 25, but his landlord found him in his chic Chelsea apartment about a week later, said John Morton, a friend who worked with Chamberlain on his TV show, which ran from 1999 until 2000.
On Saturday, the medical examiner was still investigating the cause of death. Police said there was no sign of foul play, and friends said Chamberlain seemed healthy.
Those who knew him well said he was a modern-day American dreamer who made it in New York.
"He was a real selfless pioneer who would push the envelope in art and technology - without great expectations of returns," said Adeo Ressi, a friend flying in from San Francisco to attend the memorial. "He didn't need to make a lot of money; he didn't need to be famous. He really just wanted to do great work."
Chamberlain arrived in New York in the early 1980s and got a job at Danceteria, a Chelsea club frequented by the likes of Madonna and the Beastie Boys. He modeled for designer Stephen Sprouse, performed with a band called Icon Man and appeared in a video made by David Byrne of the Talking Heads.
By 1994, Chamberlain was working for Pseudo.com, which became one of the Web's early providers of video - including "Judge Cal's High Weirdness." Chamberlain built a following with his observations on conspiracy theories, the occult, politics and cyberculture. During one show, he had his lip pierced.
By 2000, he was reporting for Pseudo.com from both the Republican and Democratic national conventions, equipped with a Web cam and keypad that was later donated to the Smithsonian Institution. He also briefly worked as a political blogger for CNN.
Pseudo.com's closing launched Chamberlain into "a dark time when he was not doing much," Morton said. Chamberlain got a job as a bartender at another trendy New York club, Crobar, now closed.
In recent years, he had found another passion - helping build metal sculptures with the Madagascar Institute, a Brooklyn art group that specializes in large-scale sculptures and "guerrilla art."
But while Chamberlain accumulated a coterie of friends - one of whom wrote about his death on the popular political Web site the Huffington Post - he was estranged from his family, only occasionally keeping in touch by phone or e-mail.
After his death, authorities and dozens of friends spent two weeks trying to find a family member, finally finding an Internet contact for Chamberlain's sister on Thursday.
His relatives hadn't seen him in more than 20 years, respecting his apparent desire not to see them, said his mother, Bette Hill, 64, of Spokane Valley, Wash.
"I think he was struggling," she said.
His friends had become his family, his mother said, and in death, "they're taking care of him. And we're very grateful for it."