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Gray organized an after-hours club called the We Ours, which took place in a small coffeehouse; in addition to welcoming open-mike acts, Gray and her jazz group performed there regularly. She signed with Atlantic Records, who declined to release the album she recorded for them. Devastated by this rejection and the breakup of her marriage (her third child was on the way at the time), Gray retreated to Canton. However, her demo tape continued to make the rounds, and she returned to L.A. to accept a publishing deal with Zomba. This in turn helped lead to a new record contract with Epic in April 1998, and Gray spent the next year recording what was to become her debut album, On How Life Is. Released in the summer of 1999, On How Life Is won glowing reviews and great word of mouth, but in spite of all that -- plus a moderate hit single in "Do Something" -- the record was initially slow to catch on. That all changed early the next year, when Gray received two Grammy nominations (for Best New Artist and Best Female R&B Vocal), and the single "I Try" started to take off on radio. "I Try" proved to be an enormous hit, and On How Life Is suddenly sold like hot cakes, entering the Top Ten and going triple platinum by the end of 2000. Gray scored a smaller follow-up hit with "Why Don't You Call Me," and also raised eyebrows with the album track "I've Committed Murder," in which the protagonist gets away with her crime. Although Gray lost out her first time at the Grammys, she was nominated again the following year for Best Female Pop Vocal thanks to "I Try," and this time won (although the song lost out on Record of the Year and Song of the Year honors).
In late 2000, Gray contributed two vocal tracks to Fatboy Slim's Halfway Between the Gutter and the Stars album; she subsequently recorded with the Black Eyed Peas, cut a duet with rap legend Slick Rick for the Rush Hour 2 soundtrack ("The World Is Yours"), and made her screen acting debut in the Denzel Washington police drama Training Day. By the time she had begun work on her second album, Gray was developing a reputation for surreal public appearances and interviews, culminating in an August 2001 incident in which she was booed for apparently stumbling over the lyrics to the national anthem. Released the following month, The Id was a determined effort to play up the crazy side of Gray's image; it entered the charts at number 11 and quickly went gold on the strength of lead single "Sweet Baby." However, in spite of guest appearances by Erykah Badu and the Red Hot Chili Peppers' John Frusciante, among others, its sales stalled much sooner than expected. During 2002, Gray appeared as herself in the blockbuster film Spider Man and also guested on Santana's Shaman. One year later, her third album -- The Trouble with Being Myself -- arrived on the shelves, although it was also a flop in commercial terms (it just barely missed the Top 40). With a new production team, including will.i.am from Black Eyed Peas and his confederate Ron Fair, Gray returned with a slicker, Tom Joyner-approved version of soul on 2007's Big, featuring collaborations with Natalie Cole and BEP's Fergie. It didn't perform much better on the charts; it debuted (and peaked) at number 39. The Sellout, a 2010 release on the Concord label, featured some self-composed songs and an appearance from Bobby Brown. Gray then signed to the 429 label and released Covered in 2012. The album featured renditions of songs by Metallica, My Chemical Romance, and Kanye West. Later that year, Stevie Wonder's 1972 R&B classic received the same treatment (and the same title), Talking Book. ~ Steve Huey, Rovi