1992–2003: Exile in Guyville; critical recognition
After asking Wood what the "coolest" indie label was, Phair called up Gerard Cosloy, co-president of Matador Records, in 1992 and she 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 18 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 blunt, honest lyrics and for the music itself, a hybrid of indie rock and lo-fi, and established Phair's penchant for exploring sexually explicit lyrics. By contrast, her trademark low, vibrato-less monotone voice gave many of her songs a slightly detached, almost deadpan character.
The release of Phair's second album received substantial media attention and an advertising blitz. Whip-Smart debuted at No. 27 in 1994 and "Supernova," the first single, became a Top 10 modern rock hit, and the video was frequently featured on MTV. Phair also landed the cover of Rolling Stone with the headline "A Rock Star Is Born." The album received positive reviews, although not as acclaimed as the debut, but was certified Gold (shipments of at least 500,000 units). It ultimately did not sell as well as expected, as it was hoped the album would introduce Phair to a wider, more mainstream audience. Following Whip-Smart, Phair released Juvenilia, a collection of some early Girly Sound tracks and several B-sides, including her cover of the 1980 song by The Vapors, "Turning Japanese."
In 1994, Phair made several live television and radio appearances in an effort to promote Exile in Guyville and Whip-Smart; she appeared on Late Show With David Letterman performing "Never Said" and "Supernova", and on The Tonight Show with Jay Leno performing an acoustic version of "Whip-Smart". She also performed "Alice Springs" live on Good Morning America.
She also appeared on the MTV alternative rock show 120 Minutes performing "Never Said", "6'1"", "Cinco de Mayo" and "Supernova" live at various times during 1994 and early 1995.
Phair's third album, Whitechocolatespaceegg, was released in 1998 after some delays, which included a disagreement about content; at one point, Matador rejected the album as submitted, and asked Phair to write a few additional radio-friendly songs for the set. The album displayed a more mature Phair, and reflected some of the ways marriage and motherhood affected her. While the single "Polyester Bride" received some airplay, and the album received many positive reviews, it was no more successful commercially than her previous records. To promote the record, Phair joined Lilith Fair. Phair performed on the main stage along with acts like Sarah McLachlan, Emmylou Harris, Sheryl Crow and Missy Elliott. She also opened for Alanis Morissette on her 1999 Junkie Tour.
Phair portrayed the role of office manager Brynn Allen opposite Robin Tunney in the 2002 film Cherish.
