Back in 1993, a young songwriter named Liz Phair came out of nowhere to drop one of the Nineties’ defining albums: Exile in Guyville. Phair came from the Chicago indie rock scene, but she had a new story to tell: the secret life of an ordinary twentysomething woman, grappling with love and sex and insecurity. The album didn’t get any mainstream airplay, but it changed the stakes for indie rock, musically, culturally, and emotionally.

On this episode of Rolling Stone’s 500 Greatest Albums, Contributing Editor Rob Sheffield tells the full story of the album, with help from Liz Phair herself, who breaks down how she channeled the "disillusionment and fury" of her twenties into an era-defining musical statement. Exile producer Brad Wood also weighs in with his memories of the time period, and Mannequin Pussy’s Marisa Dabice discusses how Phair’s “fearlessness” helped free up her own writing.

New episodes of Rolling Stone's 500 Greatest Albums release every Tuesday, only on Amazon Music.

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