After earning a bachelor's degree in 1989, Phair moved to San Francisco with a group of friends. When musician Chris Brokaw of the band Codeine came to visit her roommate, he convinced Phair to play her songs for him and was so impressed that he dared Phair to make him a tape of the songs.

Phair moved back home with her parents and tried to support herself by selling charcoal drawings. She also lived for a time in Chicago's bohemian Wicker Park neighborhood, nicknamed "Guyville" because of its male-oriented rock scene. Meanwhile, she bought a four-track tape recorder and made three cassettes that would become known as the Girly-Sound tapes, featuring Phair's vocals, low-volume electric guitar, and layers of harmonizing overdubs recorded in her bedroom at her parents' house.

Phair sent the tapes to Brokaw and Yu. In 2018 Brokaw recalled to Newsweek, "There was an urgency and a directness about [Phair's] lyrics that you find in literature and in films, but it was pretty rare to find it in rock music. And it was certainly rare to hear from a female voice." Brokaw and Yu duplicated the tapes and sent them to other underground artists and people in the music industry.

Eventually, her tapes were reviewed in fan magazines, and Phair was offered a $3,000 advance from the independent label Matador Records, which she used to record the 18 songs on Exile in Guyville. When the album was cut, producer and drummer Brad Wood worked with guitarist and sound engineer Casey Rice to create a minimal sound that highlighted Phair's vocals and guitar riffs without the support of a back-up band. The album sold more than 200,000 copies, unheard of at the time for an indie-label release, and Spin magazine selected it as album of the year.

Phair's profane self-assured lyrics, naked ambition, and feminist perspective in songs such as "Flower," "Fuck and Run," and "Help Me Mary" earned her many dedicated fans. In interviews, Phair revealed that her album was intended to be a response to the Rolling Stones' iconic double album Exile on Main St. (1972). Many critics interpreted her songs as taking direct aim at the sexism of indie-rock scenes such as those she had experienced in Wicker Park. In 2019 she told Vulture, "There's something about the society of men that thinks they have it all dialed in.… Exile was about believing in my perspective on life, against considerable pressure to conform to their takes on things. It's about showing them that I can play their game and do all right in it."

Exile in Guyville also sparked a backlash among some sectors of the alternative-rock community who expressed resentment about Phair's quick rise to stardom and privileged background. Her most notorious critic was producer and musician Steve Albini, who called Phair and several other acts that had crossed over to commercial success "frauds" (and worse) and accused them of a "calculated and overbearing hype barrage."

Source: Encyclopedia Britannica — "Liz Phair," by Laura Payne.