49. Fiona Apple, 'Extraordinary Machine'
This was the record that made Kanye West want to be the hip-hop Fiona Apple. Yet during the three years Apple labored over this ambitiously ornate song cycle, fans wondered if the album would ever see the light of day. After recording with producer Jon Brion, she scrapped the results and rerecorded most of the album from scratch. But with the pained, confessional balladry of "O' Sailor" and "Red Red Red," Apple sings with enough emotion to make Machine worth every day of the wait.
• Rolling Stone's Original 2005 Review