Phair was born in New Haven, Connecticut but was raised in a suburb of Chicago by her wealthy adoptive parents. After studying art history at Oberlin College in Ohio, Phair met guitarist Chris Brokaw (late of Come) and the pair moved to San Francisco for a brief period. After moving back to Chicago, Phair began writing songs and releasing homemade tapes under the name Girlysound, supporting herself by selling her drawings on the streets of Chicago. Soon, she was a part of the alternative music scene in Chicago and became friends with Urge Overkill, a popular band, as well as Brad Wood and John Henderson, head of Feel Good All Over, an independent label in Chicago. An attempt at recording the Girlysound tapes failed due to arguments between Henderson and Phair.
Meanwhile, Brokaw gave several Girlysound tapes to the head of Matador Records, Gerard Cosley, leading to a contract. Phair's debut album was released in 1993 and received uniformly excellent reviews. The album attracted some attention because it was structured as a response to the classic Rolling Stones album, Exile on Main Street. The critical success of her debut album meant Phair soon attracted naysayers in the indie rock scene, notably including Steve Albini, but her fanbase continued to grow.
Phair's second album received much 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. In spite of this, the album received mixed reviews and did not sell well. In 1995, Phair married Jim Staskausas (whom she later divorced), a film editor who had worked on her videos, and then released Juvenilia, an EP that included Girlysound material. She worked on her third album for a long time, delayed by the birth of a child. Whitechocolatespaceegg was finally released in 1998.
Five years later, her self-titled fourth album was released. A critical and commercial smash, it seemed to propel Phair out of the "alternative-chick" category and straight onto the pop charts. Always one to flirt with sexually explicit material, the album included a track called "H.W.C." which stood for "Hot White Cum" and was a tribute to her boyfriend's semen. The track "Why Can't I?" became a smash #1 single in the U.S.A. despite lyrics like "We haven't fucked yet, but my head's spinning".