When the Pawn...

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.

In 2010, Spin named the album the 106th-greatest of the last 25 years, and Slant Magazine named it the 79th best album of the 1990s. The album received a Grammy Award nomination for Best Alternative Album. In 2020, Rolling Stone ranked When the Pawn... at number 108 on its "500 Greatest Albums of All Time" list.

Title
The album's title is a poem Apple wrote in response to unfavorable reactions from readers of an unfavorable Spin cover story about her. Richard Harrington of The Washington Post called it Apple's version of Chumbawamba's "I get knocked down, but I get up again". "It came from being made fun of," she said, "and then, of course, it becomes a thing I'm being made fun of for."

Upon its release, When the Pawn... broke the record for longest album title at 444 characters (previously held by a volume in The Best... Album in the World...Ever!). Chumbawamba themselves would later hold the record with 2008's The Boy Bands Have Won, whose full title contains 865 characters, nearly twice as many as When the Pawn...'s. The full title is:"When the pawn hits the conflicts he thinks like a kingWhat he knows throws the blows when he goes to the fightAnd he'll win the whole thing 'fore he enters the ringThere's no body to batter when your mind is your mightSo when you go solo, you hold your own handAnd remember that depth is the greatest of heightsAnd if you know where you stand, then you know where to landAnd if you fall it won't matter, cuz you'll know that you're right"

Release
The first single, "Fast as You Can", was fairly popular and received moderate radio and video airplay. It reached the top 20 on the US Billboard Modern Rock Tracks chart and became Apple's first top 40 hit on the UK Singles Chart. The follow-up singles, "Limp" and especially "Paper Bag", which was nominated for a Grammy Award, were less successful. Apple's boyfriend at the time, filmmaker Paul Thomas Anderson, directed videos for all three singles.

In 2019, Apple collaborated with King Princess on a cover of "I Know". The song was released for Spotify's RISE program on January 25.

A reissue by Vinyl Me Please was announced in 2020 featuring a new cover chosen by Fiona herself, marking the album's first ever vinyl pressing.

Reception
In comparison to Apple's debut album Tidal, Harrington stated, "When the Pawn is a decidedly more mature work that trades in youthful melodrama for somber ruminations on shattered relationships and romantic obsession". In The New Rolling Stone Album Guide, Jenny Eliscu states that Pawn is "more musically complex and melodically advanced" than the previous album, while focusing on Apple's "sultry voice and moody piano playing". Rob Sheffield of Rolling Stone gave the album three-and-a-half out of five stars, calling it "richer, deeper and stronger than Tidal, in every way", with "a far more muscular approach to both the songs and the singing".

Entertainment Weekly's David Browne awarded the album an A grade, praising Jon Brion's production as well as Apple's songwriting: "Apple hasn't gained much in psychic confidence following the success of Tidal. On When the Pawn..., Apple presents herself as a mental shambles, and she's more than happy to tell us about it." Pitchfork originally gave the album a score of eight out of ten, with reviewer Chip Chanko praising Apple's lyrics, writing: "[Apple] seems older. Her voice is full of a heartfelt soul that seems almost timeless. While Billie Holiday would never have considered the possibility of lines like, 'It won't be long till you'll be/ Lying limp in your own hand,' Apple executes them flawlessly with a modern passion." Amy Linden of Vibe wrote: "When the Pawn... is full of images that resonate. Apple's a sad, sultry woman with a sense of who she is—even if that person isn't someone she wants to be. Once again, her pain brings us joy." In contrast, Piers Martin of NME rated it a 5 out of 10, calling it Apple's "second album of Amos-aping MTV-branded Lilith Fair fodder."

On the U.S. Billboard 200, When the Pawn... debuted at number 13 with 103,000 copies sold in first week. As of 2005, sales of the album in the United States had exceeded 922,000 copies, according to Nielsen SoundScan. On March 26, 2020, When the Pawn.. was certified Platinum by the Recording Industry Association of America.

Musicians

 * Fiona Apple – piano, vocals, synthesized bass (track 7)
 * Jon Brion – "all other instruments" (except "Love Ridden")
 * Mike Elizondo – bass (except "I Know")
 * Matt Chamberlain – drums, percussion (except "A Mistake", "I Know")

Additional musicians

 * Mike Breaux – woodwind
 * Patrick Warren – Chamberlin, Wurlitzer
 * Charlie Bisharat, Eve Butler, Susan Chatman, Armen Garabedian, Berj Garabedian, Peter Kent, Brian Leonard, Robert Peterson, Michele Richards, Edmund Stein, John Wittenberg – violin
 * Robert Becker, Denyse Buffman, Scott Haupert, Maria Newman – viola
 * Larry Corbett, Suzie Katayama – cello
 * Greg Cohen – bass guitar
 * Jonathan "Butch" Norton, Jim Keltner – drums, percussion
 * Wendell Kelly, Jean Martinelli, John Noreyko, Paul Loredo – horns

Technical personnel

 * Jon Brion – producer, mixing engineer, assistant engineer
 * Rich Costey – mixing engineer
 * Eddy Scheyer – mastering engineer
 * Ian Sefchick – mastering engineer (2020 LP)
 * Tom Banghart, Rob Brill, Greg Collins, Bryan Jackson, Steve Mixdorf, John Tyree – assistant engineer
 * Fiona Apple – design, cover art concept