About this Episode
Second albums are notoriously difficult to make. Expectations from critics and audiences alike can force an artist into a corner: not enough change and you risk repeating yourself; too much change and you risk alienating your fan base. Fiona Apple followed up her multi-platinum selling debut album, Tidal, by directly addressing her critics and confidently refining her songwriting. Released in 1999 and produced by multi-instrumentalist Jon Brion, When the Pawn... stood out from the burgeoning radio landscape of disposable pop, boy bands, and nu metal. Seeing as how Fiona Apple has been mentioned in previous episodes of WDWM, Tony felt it was time to see if her music lived up to its reputation, and Matt, a long time Fiona Apple fan, was only happy to oblige. They discuss the negative reaction to her interview in Spin Magazine and how that inspired When the Pawn..., Fiona's lyrical wit and complex rhyming schemes, her infamous MTV Video Awards acceptance speech, that incredible voice, and what makes this album a classic to this very day.