LATEST GIG: Mixing traditional country and rock and roll on his debut album, Put the 'O' Back in Country
•Son of a Gun: Born Waylon Albright Jennings (his father is the country legend who died in 2002), he's been known as Shooter his whole life. Jennings's mother, singer Jessi Colter, 61, told him that she borrowed the nickname from a friend's son—but he isn't so sure. "My dad said I got it because I pissed on a nurse after I was born," he says. "I like his version better."
•Country & West Coast: Inspired by bands like Guns N' Roses, Jennings moved to L.A. in 2000 and became a frontman for heavy-metal band Star-gunn. With the album, though, he returned to his Nashville roots—but mixed in a bit of Sunset Strip seediness.
•Whacked by Love: Four years after pointing her out at a movie premiere as "the hottest chick I've ever seen," Jennings and The Sopranos alumna Drea de Matteo, 33, are a couple—albeit an odd one. "I never thought I'd get along with a New Yorker," he admits. "But in her heart, she's a redneck too." Besides, he claims that de Matteo "has the best taste in music." What's in her iPod? "She had all of this rare Merle Haggard live," he says. "She just kicks my ass with the record collection."