In the early 1990s, Sheryl Crow seemed firmly on the path to mainstream pop stardom. As a young artist, she cut her teeth singing backup for Michael Jackson, contributed vocals to songs by Belinda Carlisle and Don Henley, and even recorded a duet with Kenny Loggins. Unsurprisingly, her first pass at recording a debut album resulted in an ultra-polished studio effort. But before its release, the Kennett, Missouri native decided to rip it up and start again, and drew inspiration from an established wellspring of creativity: the songwriting circle. Every week, Crow and a group of musicians—her boyfriend Kevin Gilbert; Bill Bottrell; and David Ricketts and David Baerwald, the members of the alternative rock group David & David—met up to work on songs. From these sessions came 1993’s Tuesday Night Music Club. The eclectic collection captured the changes coursing through culture at the time—Crow and others even wrote the torchy “Run, Baby, Run” the night Bill Clinton was elected president—but also verbalized romantic turmoil and youthful restlessness. The sassy disco-folk hit “All I Wanna Do” (which was based on a poem by noted writer Wyn Cooper) depicts late nights making mischief; in contrast, “Strong Enough” tackles the pain of insecurity and self-doubt within a relationship. Sonically, Tuesday Night Music Club also captured evolving musical trends and the burgeoning alt-rock movement; songs touched on stirring blues (“What I Can Do For You”), rootsy folk (“Can’t Cry Anymore”), jazz (the Joni Mitchell-esque “We Do What We Can”), and contemporary soft-pop (“Strong Enough”). The hit “Leaving Las Vegas” transcended genre, courtesy of spare percussion, a loping tempo, and dusky Americana vibes; it felt like the photo negative of Laurel Canyon folk. Crow’s instinct toward more casual music paid off. Tuesday Night Music Club became a massive global commercial success and she won multiple Grammys, including Best New Artist and Record of the Year for “All I Wanna Do.” And, in hindsight, the album’s sound was a blueprint for the ’90s alt-folk movement—and Crow’s expert bridging of pop and Americana presaged emerging initiatives like Lilith Fair.