Since then, Sheryl Crow has sold 20 million albums, won nine Grammys and become one of the most respected musicians in the business.
Some of her biggest fans include the Rolling Stones, Bob Dylan and Elton John. As 60 Minutes first reported in January, she's a singer, songwriter, performer and producer who also happens to be bright, beautiful and talented.
In a business where even successful groups and artists can have a commercial shelf life measured in months, Crow has been at the top now for nearly a decade. And she has done it with craftsmanship and lyricism, perseverance and drive. Correspondent Steve Kroft reports.
Her trademark is strong melodies with big memorable hooks: Good old-fashioned rock'n'roll with a Midwest twang. It's the same music she grew up listening to on the radio in Kennet, Mo., where she sang in the school choir, ran track, got straight A's, and grew up in a house filled with music.
"You know, that was our household. There was always music - always. To the point where it never occurred to me that I was gonna do something other than that," says Crow.
She graduated from the University of Missouri in voice and piano, and moved to St. Louis, where she was teaching in an elementary school when fate, disguised as a McDonald's burger commercial, beckoned.
"It wound up going network, which is national. It lasted for about a year, and I made about $40 grand. And I was making about $17 grand teaching for a year, and that was 45 minutes of work. I thought, 'Wow! This is amazing. Maybe I can do it in LA.'"
With a beat-up car and $10,000 in her bank account, she headed for California. Within a matter of months she was traveling the world, playing packed stadiums, singing back up for Michael Jackson.
With very tall hair and very short skirts, the former schoolteacher was soon receiving lots of attention, most of it unwanted. The tabloids concocted a story she was romantically involved with Jackson and had been offered $2 million dollars to have his baby.
"A Mercedes came into town visiting some friends of ours. And, because there were no Mercedes in my hometown, people were like 'Michael Jackson's in town. He's spending the holidays at the Crow's house,'" recalls Crow.
She can laugh about it now, but when the tour ended, so did her immediate prospects. For the next few years she waited tables, lived in half a dozen apartments, and shuffled audition tapes to all the wrong people.
Everyone recognized her talent, but in the image-conscious market-driven music business, talent is not the most important thing. No one knew how to package and sell a blonde-haired, blue-eyed soprano.
"I can’t say that the music industry... is one that nurtures artistry. It doesn’t," she says. "It doesn't create a comfort zone, it doesn't ask you to be creative. It doesn't ask you to be original. It asks you to fit into a format that people can make money off of."
She wrote songs for Celine Dion and Tina Turner, and sang backup for Jimmy Buffet and Don Henley, before finally falling in as lead singer with a group that called itself the Tuesday Night Music Club.
They cut an album and she made a video. It was out for a year before the song finally caught on. And, boy, did it catch on.
She won three Grammy's that year, including best song and best new artist. The Tuesday Night Music Club sold 7.5 million copies. More impressive is that nine years and three albums - all of them platinum - later, she is still on the charts, on MTV and VH1, and on the road, taking the roots of classic and progressive rock and planting them with a new generation.
She is, in her own words, a work hard, play hard, high-high, low-lows, type "A" personality. And she splits her time between a New York apartment and a 10-acre compound in the Hollywood Hills.
She writes everything she does and now produces her own albums. With Sheryl Crow, it is always about the music. She is accomplished and confident enough to play guitar with Keith Richards, or sing a duet with Pavarotti.
Her albums have sold 20 million copies, but accompanying that success is a reputation for being driven.
"I think that the negative connotations associated with driven and perfectionist usually get put into that category of 'bitch.' And I think that's just by nature of the fact that you have a woman who's at the head of a company, telling a bunch of both men and women how things have to be done," says Crow.
"My definition of 'driven?' It's been the pressure I put on myself. I bring people into that fold, ask them to give of themselves. You don't get there by just having a great time. You get there by digging deep."
Like most successful women of her age, she is torn between her career and her personal life, or lack thereof.
"The obvious things for me are a husband, a family. But I have a different kind of life. I have a life that a lot of people would trade what they have for," says Crow.
Now, her main interest is her life. And on several occasions she said if the right person came along, she's prepared to give up her career. But right now, the only steady man in her life is Scout, a mongrel of indeterminate age, whom she rescued from an animal shelter in 1993. He has been on every tour and in every recording studio since.
It's not that she hasn't had serious boyfriends, many of them famous - most notably Eric Clapton - and most recently film producer and actor Owen Wilson.
"I think people assume that I've never had any relationships, because all I've done is work," says Crow. "I've had great, wonderful, loving, lengthy relationships with some amazing people, maybe not all the right people. But certainly for the time of my life, they were the right person."
And how does she feel about turning 40?
"I love it. I'm enjoying this part of my life. I feel like I've walked through some fire, and come out the other side. And I really like where I'm at," says Crow. "There are, on occasions, when I'm standing on stage, and I hear my own voice come back, and it makes me feel full."