When the Pawn...[a] is the second studio album by the American singer-songwriter Fiona Apple, released by Epic Records in the United States on November 9, 1999.

Upon its release, When the Pawn... broke the record for longest album title at 444 characters (previously held by a volume in The Best...

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 rightThe first single, "Fast as You Can", was fairly popular and received moderate radio and video airplay.

[14] 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".

[3] 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".

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.

"[31] 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.