When The Pawn... is the second studio album by American singer-songwriter Fiona Apple, released on November 9, 1999. It is a blend of modern, alternative pop, jazz, and classical music. It features intricate string arrangements to accompany Apple's deep and insightful lyrics. Apple's powerful and passionate voice also shines through on the album, creating an emotionally powerful experience for listeners. Fiona Apple is an iconic alternative singer-songwriter from New York City. Her music often revolves around themes of depression, fear, and self-examination. She has won multiple awards for her music, including the Grammy Award for Best Female Rock Vocal Performance for her hit single "Criminal". Apple has also been praised for her live performances and her emotional lyrics. When The Pawn... was released to critical acclaim and solid commercial success. The album was praised for its production, featuring an array of jazz and classical influences. Apple's songwriting on the album was also praised for its range, with songs touching on themes such as heartbreak, depression, and determination. The lead single from the album, "Fast as You Can" became a moderate hit, reaching number 34 on the US Modern Rock Tracks chart.