Extraordinary Machine

Apple began the record with Jon Brion in 2002. Sessions moved to the Paramour Mansion in Los Angeles and the album was submitted to Sony in May 2003. It was not released. Songs leaked to the internet in 2004 and 2005, and fans mailed Sony in support of a release. The label was said to have withheld it without explanation, which led to speculation of a dispute over its commercial appeal. According to Elizondo, the decision to redo it was Apple's own. She told Rolling Stone in September 2005 that she had not had enough time to live with the songs before recording them.

Mike Elizondo and Brian Kehew rebuilt the album from Apple's piano and vocals, working at the Phantom Studio behind Elizondo's home in Westlake Village, with live drums from Abe Laboriel Jr. and Questlove. Of the eleven leaked tracks, two stayed unchanged, the title track and Waltz, and nine were rearranged. Parting Gift was new, a solo piano and vocal recorded on the first take. Apple took the cover photograph, an agapanthus bud in her front yard.

The record debuted at seven on the Billboard 200 with 94,000 copies sold, her first top-ten album, and was nominated for the Grammy for Best Pop Vocal Album. Entertainment Weekly, The New York Times and Slant each placed it first on their lists of the year's best albums. Rolling Stone ranked it 49th among the albums of the 2000s and 444th on its 2020 list of the 500 greatest albums.