No more. Messina, 30, has begun collecting payback for her perseverance. Her second album, 1998's I'm Alright, went double platinum and included three No. 1 singles, including "Bye, Bye." Burn, Messina's latest effort, is fast approaching platinum status as well, fueled by the No. 1 hit "That's the Way," which has earned her a shot at a Grammy on Feb. 21 for best female country vocal performance. Her peers are singing her praises. "Jo Dee's out of the same mold as Loretta Lynn—pure, unaffected and original," says her friend Naomi Judd. "She came up in the clubs and has paid her dues."
Messina's initiation into music actually occurred when she was growing up in little Holliston, Mass., west of Boston. One of four children of Vincent Messina, now 69 and a high school principal, and his wife, Mary, 71, president of Messina's fan club (they divorced when Jo Dee was 4), she was 13 when the death of an uncle inspired her to pour out her grief in an original song she performed at his funeral. A family friend who'd attended the service introduced Messina to a local band, and soon she found herself singing "Stand By Your Man" at a Holiday Inn. "I was terrified," she says. "But after I got offstage, it was like, 'Oh my God, I want to be back up there!' "
By 16 she was fronting her own band—with her brother Vinnie, now 32 and a computer programmer, on drums and sister Marianne, 46, a music critic, on bass—and playing covers of country favorites by the Judds and Patsy Cline.
After graduating from Holliston High School in 1987, Messina briefly considered going on to college and pursuing a law degree. "But music was my soul and my being," she says. For three years Messina honed her skills playing clubs, and in 1990 she took off for Nashville. There she entered talent competitions while working odd jobs to pay the rent. Her break came in 1993, when she earned a singing spot on Live at Libby's, a popular Kentucky radio show heard in Nashville. Producer Byron Gallimore was listening and took her under his wing.
He also introduced her to another client, the then-unknown Tim McGraw. The two became fast friends, and a year later it was McGraw—flush from his first hit—who helped finance Messina's debut album. "What made me want to help her from the beginning was her voice," says McGraw. "It is so honest and true." Messina calls him "my savior," explaining simply, "I wouldn't have a career if it weren't for him."
But the most important guy in her life turned out to be Don Muzquiz, who signed on as Messina's tour manager in 1995 and proposed to her with a 5-carat diamond last year. "We initially didn't see eye-to-eye on much," says Muzquiz, 36. "She is very spontaneous. I'm a little more indecisive." But by 1997 their relationship had become a romance.
By that time Messina's career was foundering. Deep in debt after her first tour, she was urged by her accountants to declare bankruptcy. Instead, she pushed herself even harder, playing 46 concerts during one six-week stretch. Finally "Bye, Bye" helped put Messina back in the black. Last month she moved into a restored 100-year-old home in Franklin, Tenn., outside Nashville.
Not that Messina looks to be settling down. Preparing to kick off a 75-city tour on Feb. 8, she and Muzquiz have yet to set a wedding date. "We're not looking at gowns and napkins, we're looking at lighting rigs and sound equipment," she says. "We'd have to take a day off to get married, and I don't see that happening anytime soon."
Beverly Keel in Franklin