When the Pawn... is the second studio album by the American singer-songwriter Fiona Apple. Released by Epic Records in the United States on November 9, 1999, When the Pawn... was wholly written by Apple, with production by Jon Brion.

Fiona Apple McAfee-Maggart is an American singer-songwriter. She released five albums from 1996 to 2020, all of which reached the top 20 on the U.S. Billboard 200 chart. Apple has received numerous awards and nominations, including three Grammy Awards, two MTV Video Music Awards, and a Billboard Music Award.