"When the Pawn..." is the second studio album by American singer-songwriter Fiona Apple, released on November 9, 1999, by Epic Records. The album was entirely written by Apple, with production handled by Jon Brion. It is considered one of Apple's most critically acclaimed works, earning a Grammy Award nomination for Best Alternative Album. In 2010, Spin ranked it as the 106th greatest album of the last 25 years, while Slant Magazine placed it at number 79 on its list of the best albums of the 1990s. In 2020, Rolling Stone ranked When the Pawn... at number 108 on its "500 Greatest Albums of All Time" list.
The album's title is a poem Apple wrote in response to negative reactions from readers following a Spin cover story about her. The title reflects a defiant and introspective response to criticism, encapsulating themes of self-reliance, strength, and resilience. The full title, which set a record for the longest album title at the time, reads:
"When the pawn hits the conflicts he thinks like a king
What he knows throws the blows when he goes to the fight
And he'll win the whole thing 'fore he enters the ring
There's no body to batter when your mind is your might
So when you go solo, you hold your own hand
And remember that depth is the greatest of heights
And if you know where you stand, then you know where to land
And if you fall it won't matter, 'cause you'll know that you're right."
The album's first single, "Fast as You Can," received moderate success, reaching the top 20 on the US Billboard Modern Rock Tracks chart and becoming Apple's first top 40 hit on the UK Singles Chart. The subsequent singles, "Limp" and "Paper Bag," were less successful, though "Paper Bag" earned a Grammy nomination. All three singles had accompanying music videos directed by Apple’s then-boyfriend, filmmaker Paul Thomas Anderson.
In 2019, Apple collaborated with King Princess on a cover of "I Know," which was released as part of Spotify's RISE program. A vinyl reissue of When the Pawn... was announced in 2020, featuring a new cover chosen by Apple herself. This marked the album's first ever vinyl pressing.
