At Fan Fair a few years ago, the scarlet-tressed singer introduced herself to a Curb Records executive and told him "What you guys really need over there is a redhead."
"Some people think it took a lot of courage to walk up and say something like that to a very powerful man," Messina said in a recent telephone interview, "but it was more like nerves. When I'm around powerful people, I tend to talk too much and joke around a lot."
"And this was my one chance to get to the guy," Messina said. "I couldn't talk to him in the office, but here he was out in the open."
Before the startled exec could respond ("Probably to call security and ask 'Who is this crazy woman?'" Messina said, laughing), famed Nashville producer James Stroud walked up and began raving about a bright new talent whose demo he had been listening to.
The singer he was so excited about just happened to be Jo Dee Messina, and the result of her luck and chutzpah was a Curb record contract and a hit single "Heads Carolina, Tails California" off her eponymous debut CD.
Of course, all the timing in the world won't help you if your talent can't open the door when opportunity finally does knock. And Messina had been working and preparing herself for that moment all her life.
Born and raised in the small town of Holliston, Mass., about 40 mites west of Boston, she grew up listening to and loving all kinds of music. But even then, she had a favorite.
"Country is so universal," she said. "Country talks about us as humans, how we feel, what we go through every day. In those days we had one really powerful country station that you could always pick up. I used to listen to Reba McEntire, Janie Fricke, Restless Heart, Dolly Parton, the Judds, Alabama. I loved those guys. "
Even as a young child though, she wasn't content to be solely a spectator. Fortunately she was encouraged to do what she loved by her understanding and supportive family.
"I always knew I wanted to be a singer," she said. "Always. My oldest sister, Mary Arm, used to take me to tap dancing class and to auditions for local plays like 'The Sound of music.' I was in the chorus at school. One way or another I was always singing."
With the full support of her family, Messina sang in C&W bars at 14. By 16, she had her own band, what she called the "imaginatively-named" Jo Dee Messina Band. This was something of a family affair too, with Jo Dee's brother on drums, and sister playing bass and Mom driving them to gigs.
At 19, she moved to Nashville, supporting herself by singing in talent contests.
"I used to enter those talent contests all the time, and you'd win like $50, $100 or $200," she said. "They had these contests every night of the week. Sometimes I'd make 500 bucks a week, sometimes I'd make 50. If nothing else, it taught me to manage my money well."
"I won a chance to perform on a radio show and a producer, Byron Gallimore heard me on that show," Messina said. "He took me in the studio and we started doing demos, and he started pitching me to record labels."
During this time she met and befriended another struggling artist - Tim McGraw.
"I met Tim soon after I came to Nashville," Messina said. "We were just a couple of kids kicking around, trying to get our careers going. And we've been friends ever since. We just hit it off."
Messina actually got a record deal - with RCA - before McGraw did. "When you get to be a big star, don't forget me," she said he told her.
Unfortunately the timing wasn't right for Messina to be a star yet. RCA was undergoing reorganization at the time, and Messina got lost in the shuffle. She left RCA and went back to the other record companies that had been interested in her before, but they had all signed new female artists and weren't interested in another.
"So Tim made it big first and he didn't forget me," Messina said. "He co-produced my CD, and he didn't just slap his name on it. He worked - hard. And he helped us pick out the songs we'd use. We sent him tapes to listen to while he was out on the road, and he sent us back the ones he liked. Tim is a sweet, generous guy, and he never goes back on his word."
Messina, McGraw and coproducer Gallimore sifted through more than a thousand songs to find the 10 they wanted.
One song selected was an irresistible uptempo number about chucking one's woes and responsibilities and hitting the open road. "Heads Carolina, Tails California" made an impressive showing on both the Billboard charts and CMT'S top 20 video countdown.
"Doing the video was a lot of fun," Messina said. "We went out to the desert in California" (guess the coin came up tails) spent 12 hours shooting it and it seemed like five minutes."
The second single from the CD had not been decided on at press time, but there are several strong contenders. "Do You Want to Make Something of It?" sounds like something Pat Benatar might have done had she been inclined more toward country and western. "He'd Never Seen Julie Cry" and "I Didn't Have to Leave You" are both strong ballads. "We haven't had a chance yet to get any feedback from people who have bought the record. We want to do what's going to make people happy. A lot of people say we should go with "You're Not in Kansas Anymore" or "On a Wing and a Prayer."
"Walk to the Light" is another powerful song from the CD, with spiritual aspects that everyone can relate to.
"If you listen to it," Messina said, "you've either lived it or been there or know someone who has, about the love that's long gone but she can't let go. Somebody's got to tell her, hey, don't be afraid to move on." When I intro this song in concert I say we fell in love with this song because it just shows you that no matter how low down you feel there's always hope."
Messina co-wrote one song on the album - "On a Wing and a Prayer" - and said she would like to do more writing. "But I know I have to develop my craft. There are people out there who can write ten times better the I can."
USA Today in reviewing "Jo Dee Messina" said that she brings a great deal of passion to her music, something that's lacking in much of today's "cool" country. Messina had no comment on whether country lacks passion ("I'm too much of a fan to say that about anybody. I love country music. I've been listening to Faith Hill, Martina McBride, Shania Twain and Ty England. I'm too big a fan to slam anybody.") but was excited about getting a positive review in the nation's newspaper.
"I read that review and I was like 'Oh my God!' Entertainment Weekly, which isn't even a country magazine, it's an LA-based magazine, said nice things about it (the CD) too. I was so excited."
Nor does she deny that she is passionate about what she does.
"If you've seen me sing you know it's almost like I get lost in the song," she said. "I communicate well with the audience, but I feel it. I feel these songs."