Potential girlfriends of country-rock troubadour Ryan Adams, beware: When the romance fades, you—and the rest of the world—will hear all about it. When an ex-flame (he won't say who, though he has dated Winona Ryder and singer Beth Orton) heard a song he had written about her, he says, "it weirdly reduced her to tears, but she didn't leave. Because it was just the utter, damn truth."

Emotional honesty has made Adams, 27, a favorite of Elton John's. John befriended the singer-songwriter after hearing his lovelorn Heartbreaker CD two years ago (Adams's 2001 album, Gold, made many Top 10 lists, including PEOPLE's). "He's a walking broken heart," says John. "His emotions are so out there." Although Adams lives in Manhattan, even last year's hit "New York, New York" was really about an ex, and his latest album, Demolition, is dedicated to another past love, Carrie Hamilton, the singer (and daughter of Carol Burnett) who, after battling lung cancer, died at 38 in January. "Jesus, don't touch my baby," he sings on the CD's heartbreaking coda. "She's all I've got."

Raised in North Carolina by his mom, Susan Floyd, 53, a retired schoolteacher, after her divorce from his father, David, 52, a contractor, Adams was the kind of high school student who would send love poems to a beautiful classmate, only to be mortified when she posted them on a wall for laughs ("I was humiliated," he recalls). Dropping out of school at 15, he seemed bound for stardom a few years later with the alt-country group Whiskeytown, but it disbanded in 1998. Adams admits he had a rep for being drunk onstage. "There comes a point when that stuff just becomes sad," he says. "I still have my crazy side, but it isn't who I am anymore."

Starring with Willie Nelson in Gap commercials has added to his buzz; recently that girl from high school wrote him a letter. "I must have drafted five or six responses," he says, "but in the end I never said a word."