Frustrated, Crow suffered a bout of severe depression that lasted around six months. She revived her career as a session vocalist, however, and performed with the likes of Sting, Rod Stewart, Stevie Wonder, Foreigner, Joe Cocker, Sinead O'Connor, and Don Henley, the latter of whom she toured with behind The End of the Innocence. She also developed her songwriting skills enough to have her compositions recorded by the likes of Wynonna Judd, Celine Dion, and Eric Clapton. Thanks to her session work, she made a connection with producer Hugh Padgham, who got her signed to A&M. Padgham and Crow went into the studio in 1991 to record her debut album, but Padgham's pop leanings resulted in a slick, allad-laden record that didn't reflect the sound Crow wanted. The album was shelved, and fearing that she'd let her best opportunity slip through her fingers, Crow sank into another near-crippling depression that lingered for nearly a year and a half. However, thanks to boyfriend Kevin Gilbert, an engineer who'd attempted to remix her ill-fated album, Crow fell in with a loose group of industry pros that included Gilbert, Bill Bottrell, David Baerwald, David Ricketts, Brian MacLeod, and Dan Schwartz. Dubbed the Tuesday Night Music Club, this collective met once a week at Bottrell's Pasadena recording studio to drink, jam, and work out material. In this informal, collaborative setting, Crow was able to get her creative juices flowing again, and the group agreed to make its newest member -- the only one with a recording contract -- the focal point.

Crow and the collective worked out enough material for an album, and with Bottrell serving as producer, she recorded her new official debut, titled Tuesday Night Music Club in tribute. The record was released in August 1993 and proved slow to take off. Lead single "Run Baby Run" made little impact, and while "Leaving Las Vegas" attracted some attention through its inclusion in the acclaimed film of the same name, it reached only the lower half of the charts. A&M took one last shot by releasing "All I Wanna Do," a song partly written by poet Wyn Cooper, as a single. With its breezy, carefree outlook, "All I Wanna Do" became one of the biggest summer singles of 1994, falling just one position short of number one. Suddenly, Tuesday Night Music Club started flying out of stores, and spawned a Top Five follow-up hit in "Strong Enough" (plus another minor single in "Can't Cry Anymore"). Crow was a big winner at the Grammys in early 1995, taking home honors for Best New Artist, Best Female Rock Vocal, and Record of the Year (the latter two for "All I Wanna Do"). Her surprising sweep pushed Tuesday Night Music Club into the realm of genuine blockbuster, as its sales swept past the seven million mark. After close to a decade of dues-paying, Crow was a star.

Unfortunately, success came at a price. In 1994, Crow had been invited to perform "Leaving Las Vegas" on Late Night With David Letterman. In a brief interview segment, Letterman asked if the song was autobiographical, and Crow offhandedly agreed that it was. In actuality, the song was mostly written by David Baerwald, based on the book by his good friend John O'Brien (which had also inspired the film). Having been burned by the industry already, some of the Tuesday Night Music Club took Crow's comment as a refusal to give proper credit for their contributions. Baerwald in particular felt betrayed, and things only got worse when O'Brien committed suicide not long after Crow's Letterman appearance. Although O'Brien's family stepped forward to affirm that Crow had nothing to do with the tragedy, the rift with Baerwald was already irreparable. Some Club members bitterly charged that Crow's role in the collaborative process was rather small, and that the talent on display actually had little to do with her. Tragedy struck again in 1996 when Crow's ex-boyfriend, Kevin Gilbert, was found dead of autoerotic asphyxiation.

Stung by the charges, Crow set out to prove her legitimacy with her second album when the heavy touring for Tuesday Night Music Club finally ended. Bill Bottrell was originally slated to produce the record, but fell out with Crow very early on, and the singer ended up taking over production duties herself. However, she did bring in the noted team of Mitchell Froom and Tchad Blake as assistant producer and engineer, respectively. Froom and Blake were known for the strange sonic experimentation they brought to projects by roots rockers (the Latin Playboys) and singer/songwriters (Richard Thompson, Suzanne Vega), and they helped Crow craft a similarly non-traditional record. Released in the fall of 1996, Sheryl Crow definitely bore the stamp of the singer's personality and songwriting voice, especially in the idiosyncratic lyrics; plus, she was now writing mostly with her guitarist, Jeff Trott, proving that she could cut it without her estranged collaborators. The singles "If It Makes You Happy," "Everyday Is a Winding Road," and "A Change Would Do You Good" were all radio smashes, and "Home" also became a minor hit. Sheryl Crow went triple platinum, and Crow brought home Grammys for Best Rock Album and another Best Female Rock Vocal (for "If It Makes You Happy").

Crow toured with the Lilith Fair package during the summer of 1997 (the first of several times), and subsequently wrote and performed the title theme to the James Bond film Tomorrow Never Dies. In the fall of 1998, she returned with her third album, The Globe Sessions. A more straightforward, traditionalist ock record than Sheryl Crow, The Globe Sessions didn't dominate the airwaves in quite the same fashion, but it did become her third straight platinum-selling, Top Ten LP, and it won her another Grammy for Best Rock Album. It also spawned two mid-sized hits in the Top 20: "My Favorite Mistake" and "Anything but Down." In 1999, she contributed a Grammy-winning cover of Guns N' Roses' &"Sweet Child o' Mine" to the soundtrack of the Adam Sandler comedy Big Daddy. She also performed a special free concert in New York's Central Park, with an array of guest stars including Keith Richards, Eric Clapton, Chrissie Hynde, the Dixie Chicks, Stevie Nicks, and Sarah McLachlan. The show was broadcast on Fox and later released as the album Live in Central Park, just in time for the holidays. "There Goes the Neighborhood" won her another Grammy for Best Female Rock Vocal; however, partly because of some shaky performances, the album flopped badly, not even going gold.

Hit with a case of writer's block, Crow took some time to deliver her fourth studio LP. In the meantime, she produced several tracks on Stevie Nicks' 2001 album, Trouble in Shangri-La, and also recorded a duet with Kid Rock, "Picture," for his album Cocky. Finally, in the spring of 2002, Crow released C'mon C'mon, which entered the LP charts at number two for her highest positioning yet. It quickly went platinum, and the lead single, "Soak up the Sun," was a Top 20 hit and another ubiquitous radio smash. The follow-up, "Steve McQueen," was also a lesser hit. At the beginning of 2005 it was announced that there would be two simultaneously released new albums available by the end of the year. The project was then scaled back to the single disc Wildflower which saw release at the end of September. ~ Steve Huey, All Music Guide