She was born in New Haven, Connecticut, but was raised by her adoptive parents in Cincinnati, Ohio, and Winnetka, Illinois, a suburb of Chicago.
Phair attended Oberlin College, a liberal arts school in Ohio, with the intent of becoming a visual artist. Songwriting was a popular pastime for many of the students, so Phair picked it up alongside her drawing. She recorded her early efforts under the moniker Girly Sound and caught the attention of the indie label Matador, who offered her a record deal.
Her debut album, Exile In Guyville, skewered Chicago's male-dominated alt rock scene with songs like "6'1," "Never Said," and "Stratford-On-Guy."
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