Bernice and Wendell Crow encourage their four children to take up music and even play piano and trumpet, respectively, in a big band. Daughter Sheryl begins playing the piano at an early age. "We had four pianos in the house, and we all practiced at once," Crow tells PEOPLE of her childhood in the farming town of Kennett, Mo. "Mom stood in the kitchen cooking and monitored us, but I still don't know how she could hear."
Crow graduates from the University of Missouri with a degree in piano and voice and takes a job teaching elementary in St. Louis. After breaking up with her devout Christian fiancé who, according to PEOPLE, insists that she sing exclusively "for the Lord," she moves to L.A. to pursue music.
After crashing a closed audition, Crow lands a gig as a back-up singer on Michael Jackson's 18-month Bad world tour. "He was never around," Crow, who sang "I Just Can't Stop Loving You" as a duet onstage with the King of Pop, tells PEOPLE in 1994. "For all the time I saw him, I could've been on tour with Tom Jones."
Crow releases the stripped-down, lyric-driven Tuesday Night Music Club. It eventually reaches No. 3 on the Billboard Albums chart on the strength of two Top 5 singles, "All I Wanna Do" and "Strong Enough." "I thought the album was going to die a slow death," she tells PEOPLE. "But it turned out differently."
With her self-titled second album, Crow's mix of folk, pop and rock wins over the masses and critics, but not retailer Wal-Mart. The chain refuses to sell Crow's album because the track "Love Is a Good Thing" features the lyrics: "Watch our children while they kill each other/With a gun they bought at Wal-Mart discount stores." It peaks at No. 6 on the Billboard albums chart and scores two Grammys for Best Rock Album and Best Female Rock Vocal Performance for the hit "If It Makes You Happy."
After crafting a casual, Birkenstock-favored, hippie image with her first album, Crow turns heads in a Vivienne Westwood skirt, Prada boots and straightened hair in the video for "If It Makes You Happy." "It was a very big departure. It would be like the Black Crowes' showing up in Versace," MTV's senior wardrobe stylist Jimmy Hanrahan tells Entertainment Weekly. "It's cool and I think she can pull it off, but I wonder whether she's comfortable in it."
Fellow artist Sarah McLachlan launches the Lilith Fair festival featuring all-women musicians, which hits 35 cities in seven weeks. Crow only appears at two dates because she is headlining her own tour. "Music tends to represent what's going on with youth," Crow tells EW. "Now you have a lot of females who are stepping up to represent women in America, becoming role models for young girls."
Crow releases The Globe Sessions, her most personal album to date. "It feels like I'm standing there with no clothes on and I haven't worked out in a long time," she says to Billboard. "I'm really private about who I've had relationships with, and I don't talk about them in the press. I don't even really talk about them with the people around me."
Crow appears in The Minus Man, as the victim of a serial killer played by Owen Wilson. The costars hit it. Crow tells the Toronto Sun in 1999, "He's seen me play a lot. And he loves it. It's funny because he's only ever been to two rock concerts and one of them was mine."
Crow celebrates her 40th birthday on the beach in Oahu, shooting the video for "Soak Up the Sun" from her upcoming album C'mon, C'mon. The cast and crew, who include surf pros Malia Jones and Pake, give the singer a custom-made board as a present. "Not only did she manage to stand up, she rode a wave in," director Wayne Isham tells In Style.
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