Chappelle may hold the record for most failed sitcoms: "I've done 10 or 11 pilots for network television, which is ridiculous," he told reporters recently. His first shot at TV fame, 1996's Buddies, lasted only four episodes. "At a certain point I (asked myself), what is it I wanted to do, and is there a way I could do something that was in line with my sensibility? And cable was kind of the remedy." The comic, 30, recently signed a deal with Comedy Central reportedly worth $50 million to do two more seasons of his Emmy-nominated Chappelle's Show. "Everything they told me wouldn't work on television, they were wrong about," said Chappelle, who also has a Showtime special, Dave Chappelle: For What It's Worth, airing Sept. 4.
2. He found his calling young
At 14, Chappelle knew laughter was in his blood. "When I read an article about Bill Cosby, I decided I was going to make a living doing (comedy). That was 1987." He prowled the Washington, D.C., club scene for open-mic nights – with his mother, Unitarian minister Yvonne Seon. "That was good, because when you start out, your inclination is to be dirty because it's easier," he said. "She forced me out of that." He then enrolled in the Duke Ellington School for the Arts, and after high school moved to New York City to be a comic. "He has a rare talent for making us laugh at ourselves," his mother told PEOPLE.
3. He speaks his mind
In 1998, Chappelle took a stand against FOX, which he says wanted to change a key character from African-American to white in a sitcom based on his life as a struggling comedian in New York City. Chappelle accused the executives of being afraid of producing an all-black show. "They used phrases like 'bring universal appeal,'" he told the St. Petersburg Times. He ended up quitting the project, saying their way would be "ridiculous," but that if he made it his way, it wouldn't get support. "Either way, the odds are you'll fail."
4. He likes the simple life
When Chappelle isn't touring, he can often be found at his Yellow Springs, Ohio, farm, near Cincinnati. He spent summers there as a teenager visiting his father, William, a voice and music professor at Antioch College, after his parents divorced in 1978. (William died in 1998.) "So these people are used to me," he said recently. "It usually goes down like this: I'll come home, and for the first week, everybody will freak out when they see me. 'Hey, look. It's Dave Chappelle.' And then they just get used to me, and I'm like any other guy in the neighborhood. Like if it was The Simpsons, I'm Krusty the Clown."
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Yoga? Meditation? Chanting? Nah. Chappelle's favorite mode of relaxation is the ancient art of skateboarding. "I think extreme sports are really good for relieving stress," said Chappelle, who first got wheel-y with it when he was young but took it up again when his son, Sulayman, 3 (with wife Elaine), was born. When he's on the road, Chappelle drops in on local skate parks. "That's my favorite part of touring. That, and the shows. I highly recommend it for those who have strong bone structure."