Initially circulated among in-the-know music fans in Chicago, Phair's Girlysound cassettes contain startlingly personal songs accompanied by raw, low-fi guitar and fed through layers of overdubs. The tapes quickly became one of alternative rock's most sought-after bootlegs and brought Phair to the attention of Matador Records, which released her gushed-over debut album, 1993's Exile in Guyville (the title a sly comment on Chicago's incestuous indie rock scene.) Notoriously conceived as a song-by-song response to the Rolling Stones' Exile on Main Street, the album was instantly embraced by critics and fans for its startling assurance, potent variety of rock, pop and folk textures, and for the amazing arsenal of characters, voices and ideas embedded in Phair's songs. The album would see out the year atop endless best of lists, propel Phair to the cover of Rolling Stone, and earn a place as one of rock's most acclaimed solo debuts.
Guyville's follow-up, 1994's half-million-selling Whip Smart, broadened Phair's sonic palette, expanded on her frank explorations of sex and relationships, and produced a riff-heavy modern rock hit in Supernova. Phair later joined the lineup of the enormously successful Lilith Fair as one of the favorite artists in the 1998 and 1999 tours, watching the creative and commercial climate for female artists flourish under her influence. In Phair's sweeping third album, 1999's whitechocolatespaceegg (a reference to her new baby boy's shiny bald head), the signature character songs and strummed guitars remained, but it revealed a noticeably more assured Phair, both emotionally and musically, and created a formidable leap from the homespun intimacy of her previous work, prompting a new round of critical accolades.
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