Sprawled in striped pajama bottoms by the pool of his plantation-style home near Nashville, Kenny Chesney is a walking billboard for his new album: no shoes, no shirt, no problems. At 34, he has his second Academy of Country Music nomination for Top Male Vocalist. But for the moment his mind is back at Chucky's Trading Post, a Johnson City, Tenn., Mexican restaurant where he played in the late '80s. "I got $5 an hour plus as many enchiladas as I wanted," he recalls. "At first I didn't get a tip. I put my guitar in my truck and said 'Man, do I suck that bad?'"

Flash-forward a few hundred smoky Saturday nights and Chesney has two double-platinum discs under his belt, driven by such hits as 1999's "She Thinks My Tractor's Sexy." And last month No Shoes, No Shirt, No Problems debuted at No. 1 on the album chart. The new songs are "a real move forward," says critic Peter Cooper of Nashville's The Tennessean. "He has weightier, really mature songs."

Case in point is the elegiac "I Can't Go There," which Chesney wrote after his November 1999 breakup—three weeks before his planned wedding—with Mandy Weals, a Nashville health care administrator he had dated for two years. Afterward, "I went down to the Caymans by myself, which was a mistake—because that's where we always went." Chesney met a local fisherman and joined him on his boat, but "looking out over the water, that's when I realized that emotionally, mentally and physically I couldn't be there." So he went home and wrote the song about places they used to go together. "Part of me still hasn't let her go," says the unattached Chesney. "She knew me when I was sick, p——- off, happy. It's hard to let someone else get to those places." Backing him up on the ballad is his neighbor Tim McGraw, a pal since they were hopefuls in the early '90s. "Everything can be so plastic these days," says McGraw, 35. "His music is honest."

While touring together near Buffalo in June 2000, the friends got into a legal scrape. In a backstage parking area, a police officer's daughter let Chesney sit on her father's horse. He rode it briefly, and two cops told him to dismount. A scuffle ensued, and McGraw rushed to Chesney's aid. Chesney was charged with disorderly conduct, McGraw with assault. After a jury cleared them in May 2001, McGraw's wife, Faith Hill, wept with relief. Chesney says the pair could have pleaded to lesser charges and avoided a trial, "but the public would've thought we were guilty, that we were a couple of rednecks."

Actually, his neck is just really, really tan. But Chesney is certified country, the second-most famous musician (after Chet Atkins) from rural Luttrell, Tenn., where he was the only child of hairdresser Karen Chandler, 53, and now-retired teacher Dave Chesney, 59, who split before Kenny was born. Going to Tennessee football games with his dad inspired Chesney's lifelong passion for sports, but on the side "I remember making up songs in my head," he recalls. "Just stupid stuff."

At East Tennessee State University Chesney honed his writing and got a degree in marketing. Moving to Nashville in 1991, he parked cars before cutting his first album, In My Wildest Dreams. It tanked financially, but Chesney built an audience one roadhouse at a time.

Nowadays, when the bus parks in Nashville, Chesney often visits McGraw and Hill ("Tim makes the best vegetable soup," he says). Does he envy their domestic bliss? "Who doesn't?" Chesney says. But for now, he's hitched to his career. "If I were to marry someone, they would be second," he admits, rocking on his veranda. "But it sure would be good to have somebody to sit on this porch with every now and then."

Richard Jerome
Kelly Williams in Nashville