Sheryl Crow's discography has run the gamut. From country ballads to Stones-y rock to Dylan-esque folk, the singer-songwriter's multiple genre-bending hits took her from small-town music teacher to the world's biggest stages.

She first introduced herself via 1993's Tuesday Night Music Club, with an ad hoc band of musicians including Bill Bottrell, Kevin Gilbert, Brian MacLeod, David Baerwald and others. Her debut spawned the smash hit "All I Wanna Do," showcasing Crow as clever songwriter, but its collaborative nature meant that Crow still had some proving to do.

In the two years that followed, Crow and the rest of her initial collaborators fell away from one another.

She performed "Leaving Las Vegas" from Tuesday Night Music Club during a 1994 appearance on the Late Show with David Letterman and, in a moment of carelessness, said it was autobiographical. (The song was primarily written by Baerwald.) A grueling tour and a make-or-break appearance at the 1994 Woodstock festival brought Crow to the forefront of the '90s, but the slip up on Letterman seemed to trigger a series of tragic events.

John O'Brien, a friend of Baerwald's who wrote a novel titled "Leaving Las Vegas" that inspired the song, died by suicide in the spring of 1994. Baerwald then wrote an icy article for the L.A. Weekly, essentially accusing her of causing him to betray O'Brien, who was by then in the throes of alcohol addiction. The death was not directly tied to Crow, and O'Brien's family made a point to note it was actually the result of his own "long, long bloody trip."

Still, the unfortunate incident hung over Crow, who was determined to prove herself despite the obstacles for female musicians at the beginning of the post-grunge era. A change, it seemed, would do her good. So Crow enlisted a new collaborator, Jeff Trott, for sessions that would produce her self-titled sophomore album.

Watch Sheryl Crow Perform 'If It Makes You Happy'

Trott was just about to leave for a tour with the Wallflowers when Crow asked if he'd come to New Orleans to write with her. (He'd go on to become one of Crow's longest standing co-writers.) She also invited a few familiar faces, like Bottrell and MacLeod, despite their disagreements. “My only objective on this record was to get under people’s skin," she told Rolling Stone in 1996, a few weeks after the album's release, "because I was feeling like I had so much shit to hurl at the tape.”

Crow chose to produce the album on her own and play the majority of the instruments, as she continued to move away from the persona portrayed on her first album. The cover image of a denim-donning girl who sang about drinking beer at noon on Tuesday turned into a portrait of a woman in a leather jacket with darkened makeup and a stern stare.

“We had a day of press in Europe and I had two guys come in and say, ‘Your cover – you look so sad. Are you sad?’ Well, doctor, it’s actually a photo,'" Crow told Rolling Stone. “I don’t feel like the same person. I don’t feel like that accessible girl in the jeans shirt with a dog and, ‘Hey, come sit down; I’ll tell you everything.’ I don’t feel like that person anymore. I do feel like having a certain amount of space between me and the world around me. I had given it all away. And now I’m trying to get some of it back.”

The singles on Sheryl Crow were evidence of that reconciliation with herself. The lead single, "If It Makes You Happy," which Crow later said was inspired by Tom Petty's anthemic style of songwriting, could have just as easily applied to her former bandmates as herself.

She never answered the question of why the hell she's so sad. "I think that song, at the moment when it came out, was the big 'F-you' song," she told CBC Radio in 2019. "It was like girl power."

Watch Sheryl Crow Perform 'Everyday Is a Winding Road'

Nevertheless, Crow wasn't necessarily inclined to turn the spotlight on herself alone. Tragedy occurring in the surrounding world impacted the songwriting, as her own personal grief had. Sheryl Crow included some of the most striking politically tinged messages of her career – notably on the issue of women's rights. At the time, abortion clinics, doctors and patients were becoming the victims of violent, sometimes fatal, attacks from protestors – and Crow took her listeners to the front lines.

"My friend, O' Lawdy went to take care of her own body," Crow sang on "Everyday Is a Winding Road," the second single from the album. "She got shot down in the road. She looked up before she went, said 'this isn't really what I meant,' and the Daily News said, 'Two with one stone.'"

Some of Crow's writing even put her own sales in harm's way. "Watch out sister, watch out brother; watch our children while they kill each other with a gun they bought at Walmart discount stores," she sang on "Love Is a Good Thing." "Welcome to the hallway metal detector, just been installed." Walmart refused to stock the album in its stores.

“It was sad because for someone like me who’s from a small town, Walmart was the only place you could buy records at that time," Crow told NME in 2021. "They gave me the option of changing it to Kmart – another discount center – but to me that seemed even more unscrupulous. In the end, we lost a lot of record sales but we also gained press: It created a story and made people curious."

Crow was also influenced by the hardship she saw while visiting Bosnia in 1995 with Hillary Clinton.

Listen to Sheryl Crow Perform 'Love Is a Good Thing'

"I really experienced something I'd never seen before, which was what it looks like to be in a war-torn area and meet people who had suffered through that," Crow told Rolling Stone Country in 2014. "Part of [Clinton's] goal was to speak to the women and children in those villages.

"The moment we went into Bosnia, the whole genocide was happening in Rwanda and we sat back and watched it," Crow added. "Yet Bosnia seemed to be kind of a stronghold in Europe and we needed the military presence there. I came home really struck by the question of why we invest in some countries, and other countries we don't."

Upon her return, she wrote "Redemption Day," a song that was later covered by Johnny Cash.

There was more hardship after the bulk of the LP had been recorded. Gilbert, who had been Crow's boyfriend during sessions for her debut, died four months before the second album's release from autoerotic asphyxia, a fatal incident that was deemed an accident. To a degree, her feelings about their split remained unresolved.

"I feel like, I think I’ve done everything that I can, and now how is it I still can’t do anything right?" she told Rolling Stone in 1996. "It’s almost like a father relationship where you are just always trying to please somebody, and you can’t really. And I still don’t know. But part of that got worked out on the record.”

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