When the Pawn...

Epic released the album on 9 November 1999, with Jon Brion producing. Its full title is a 90-word poem that Apple wrote in response to readers' reactions to a Spin cover story about her. She said it came from being made fun of, and then that becoming a thing she was made fun of for. At 444 characters it set a record for the longest album title. Brion played all the other instruments on every song except Love Ridden, with Matt Chamberlain on drums and percussion, Patrick Warren on Chamberlin and Mike Elizondo on bass on three songs. Jim Keltner plays drums on I Know.

Fast as You Can, Limp and Paper Bag were the singles. Paper Bag earned Apple a Grammy nomination for Best Female Rock Vocal Performance at the 43rd Grammy Awards. The album debuted and peaked at 13 on the Billboard 200 with 103,000 copies sold in its first week, and the Recording Industry Association of America certified it Platinum on 26 March 2020. Rob Sheffield of Rolling Stone gave it three and a half stars and called it richer, deeper and stronger than Tidal in every way. David Browne of Entertainment Weekly gave it an A. Slant placed it 79th among the albums of the 1990s, and Rolling Stone ranked it 108th on its 2020 list of the 500 greatest albums.