Growing out of the American underground of the late '80s, Liz Phair fused lo-fi, indie-rock production techniques and styles with the sensibility and structure of classic singer/songwriters. Exile in Guyville, Phair's debut album, was enthusiastically praised upon its 1993 release and it spawned a rash of imitators, particularly American female singer/songwriters, over the following years. For her part, Phair wasn't able to break into the mainstream, even with the support of the press and MTV. Whip-Smart, her second album, was heavily promoted upon its 1994 release, yet despite its relatively strong chart positions, it was viewed as a disappointment and Phair's momentum declined steadily during the mid-'90s, as she took several years to record her third album.

Liz Phair (b. April 17, 1967) was born in New Haven, Connecticut and adopted by wealthy parents, who raised her in the Chicago suburb Winnetka. After high school, she studied art at Oberlin College in Ohio. At Oberlin, she became fascinated with underground indie-rock and eventually became friends with guitarist Chris Brokaw, who later joined Come. Following their college graduation, Phair and Brokaw moved to San Francisco, where she tried to become an artist.

Eventually, Brokaw moved out east and Phair moved back to Chicago, where she began writing songs. Soon, she began releasing home-made tapes of these songs under the name Girlysound. While she supported herself by selling her charcoal drawings on the streets of Wicker Park, she was becoming involved in various portions of the Chicago alternative music scene; in particular, she became friends with Urge Overkill, a drummer named Brad Wood and John Henderson, the head of the Chicago-based indie label, Feel Good All Over. Henderson and Phair tried to re-record some of the Girlysound tapes with Wood, yet the pair had a falling out during the sessions, leaving Wood as Phair's only collaborator. Brokaw, who had by then joined Come, was still receiving Girlysound tapes and he gave a copy to Gerard Cosley, the head of Come's record label, Matador. By the summer of 1992, Matador had signed Phair and she began recording her debut album in earnest.

Adapting its title from an Urge Overkill song, Exile in Guyville, her debut album, was released to strong reviews in the summer of 1993. Many articles focused on Phair's claim that the double-album was structured as a response to the Rolling Stones' classic Exile on Main St. Over the course of the year, the record slowly built a dedicated following in America, both among critics and alternative rock fans. At the end of the year, it topped many Best-of-the-Year critics polls, including The Village Voice and Spin. With all the attention focused on Phair, many indie-rock figures -- particularly members of the Chicago noise-rock scene, such as Steve Albini -- were developing a resentment towards her and launching an attack at the singer and the heavy media attention Exile in Guyville received. The criticism couldn't halt the progress of Phair and Exile and in early 1994, she launched her first tour, which was plagued by her stage-fright. Around the same time, MTV began airing "Never Said" and, as a result of all the hype, the album briefly appeared in the charts in February. By the spring of 1994, it had sold over 200, 000 copies -- a remarkable number for an independent release.

By that time, Phair had begun work on her follow-up record. Matador had signed a distribution deal with Atlantic Records in 1994, and her second album was going to be one of the first to be heavily promoted by the alliance. Indeed, Whip-Smart was released to a whirlwind of media attention -- including Phair, dressed only in negligie, on the cover of Rolling Stone -- that outweighed her celebrity. Though Whip-Smart debuted at number 27 upon its fall 1994 release. "Supernova," the first single from the album, received heavy airplay on MTV and alternative rock radio, becoming a Top Ten modern rock hit. However, Whip-Smart received mediocre reviews and never developed into the hit that it was expected to be. Phair didn't tour to support the album and was slow to deliver a second single. By the time the title track was released as a single in the spring of 1995, the album had disappeared from the charts.