Phair’s entry into the music industry began when she met guitarist Chris Brokaw, a member of the band Come. Brokaw and Phair moved to San Francisco together, and Phair tried to become an artist there. After being unsuccessful as an artist in San Francisco and moving back to Chicago, Phair began writing songs and recording homemade tapes under the name Girly Sound, and supported herself by selling her charcoal drawings on the streets of Wicker Park. She became part of the alternative music scene in Chicago and became friends with Material Issue and Urge Overkill, two of Chicago’s upstart bands to go national in the early 1990s, as well as Brad Wood and John Henderson, head of Feel Good All Over, an independent label in Chicago.
1992–2003: Exile in Guyville, Whip-Smart & Whitechocolatespaceegg
After asking Wood who the “coolest” indie label was, Phair called up Gerard Cosloy, co-president of Matador Records, in 1992 and asked him if he would put out her record. Coincidentally, Cosloy had just read a review of Girly Sound in Chemical Imbalance that very day and told Phair to send him a tape. Phair sent him a tape of six Girly Sound songs. Cosloy recalls: “The songs were amazing. It was a fairly primitive recording, especially compared to the resulting album. The songs were really smart, really funny, and really harrowing, sometimes all at the same time. . . . I liked it a lot and played it for everybody else. We usually don’t sign people we haven’t met, or heard other records by, or seen as performers. But I had a hunch, and I called her back and said O.K.” Cosloy offered a $3,000 advance, and Phair began working on a single, which turned into the eighteen songs of Exile in Guyville.
Exile in Guyville was produced by Phair and Brad Wood, and released in 1993. The album received uniformly excellent reviews. The album received significant critical acclaim for its very blunt, honest lyrics and for the music itself, a hybrid of indie rock and pop. The album established Phair’s penchant for exploring sexually explicit lyrics such as in the song “Flower”. The release of Phair’s second album received substantial media attention and an advertising blitz. Whip-Smart debuted at #27 in 1994 and “Supernova”, the first single, became a Top Ten modern rock hit, and the video was frequently featured on MTV. Phair also landed the cover of Rolling Stone Magazine with the headline “A Rock Star is Born.”