He's more than just some yokel who humped a dead moose and painted his dad's car on MTV. In 20 years of championing DIY, Tom Green has worked in media across the spectrum, from guest hosting The Late Show to producing a live talk show in his living room.

As such, it should come as no surprise that Green is taking on stand-up. But unlike those trying out live comedy as a second act hoping to cash in on waning celebrity, stand-up is what got Green started in the first place.

"I did it when I was a teenager, and loved doing it," Green says from his adopted home of Los Angeles. It's just that when he was back in Ottawa, spending school nights at Yuk Yuk's, other opportunities came calling.

"I was in this rap group and we got a record deal," Green says. "I abruptly quit doing stand-up and just focused on that." The group, Organized Rhyme, became regional celebrities, but after two years followed the industry's traditional boom-and-bust cycle. Green moved back into his parents' basement, but stayed focused.

"I went back to school," he says, where he studied broadcasting. "Then I started my show on public access TV, did that for years in Canada before it got picked up by MTV." Debuting in 1999, The Tom Green Show was groundbreaking not only in its candid guerilla style and flat-out weirdness—like Green slithering underneath a cow and tenderly suckling its milk-squirting udders—but also in its jarring introduction of reality. Green made onlookers the subject, forcing bystanders to react to his hijinks. It paved the way for Jackass, a fact Steve-O later pointed out to Green.

In March of 2000, Green was diagnosed with testicular cancer. Treating the disease as he would anything else, he filmed everything. For the blasé young viewers of MTV, Green's public battle with cancer was enlightened and inspired.

He went on to write, produce, and directed the film Freddy Got Fingered. Then Green got a chance like no other. When his idol David Letterman went on sick leave in 2003, Green got the chance to guest host. Of all the places this life has taken him, including a trip to Afghanistan, Green says that hosting Letterman was the most overwhelming of all.

In 2006, he started his own live talk show on the internet, filmed from his living room. A technological feat at the time, Green was able to bypass any broadcasters, standards, or bosses to deliver his material unmolested, a model that's recently come into vogue in podcasting. After some 500 episodes, Green began feeling the pull of something else.

"In the back of my mind for all these years it was like, 'Man, I'd like be getting out and doing more stand-up in front of audiences,'" Green says. And so he did what he's done so many times before: He got up each day and worked toward the goal. Green recorded his first one-hour special in September, which will be released in February on a yet-unnamed cable network.

While he's always in good spirits—at least in the public eye—Green was especially tuneful about where he is after 20 years and countless projects.

"I don't necessarily have to be doing stand-up right now," he explains. "But to me it's the root of all comedy, and it's just a great time in my life to be able to take a couple of years and do stand-up and focus on it—really develop a skill that I've wanted to have."