Background
In the summer of 1991, Phair wrote and recorded songs on audio cassette tapes, which she circulated using the moniker Girly Sound, in Chicago. Initially, she sent out only two tapes, one to Tae Won Yu, from the band Kicking Giant, and another to Chris Brokaw, from the bands Come and Codeine. Multiple copies of these tapes were made, generating a buzz around Phair. Eventually, the Girly Sound tapes started to get underground hype, appearing in several independent publications.
John Henderson, owner of the Chicago indie label Feel Good All Over, heard the tapes and contacted Phair. Soon she moved into his apartment and started playing her songs to him. Henderson brought in producer Brad Wood to help develop the 4-track demos into full songs. Originally, Phair's recordings were supposed to come out on Henderson's label. However, the whole process was made difficult by the fact that he and Phair had opposite ideas regarding what direction to take in terms of sound. Henderson preferred a stripped-down but precise sound, possibly with outside musicians, while Phair wanted a fuller sound. Phair has stated, "We both wanted something for me. He was projecting onto me what he wanted my music to come out like, which was wrong. So I blew him off." Eventually, Henderson stopped showing up at the studio, which made Phair move out of his apartment and start working exclusively with Brad Wood on what would become Exile in Guyville.
Eventually, a Girly Sound tape had made it to the head of Matador Records. Despite the outcome of their recording sessions, Henderson tipped off Brad Wood that Matador Records was interested in Phair. When Matador was contacted by Phair in 1992, they signed her. Gerard Cosloy, co-president of Matador, stated that "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 okay."
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