Shadowboxer

Shadowboxer was Apple's debut single, released on 1 July 1996. Its lyrics explore the dangers of desire and vulnerability, and Apple described it as a song about angry desperation, about knowing something is not good for you and wanting it anyway. The credits name Jon Brion on vibraphone and tack piano, Danny Frankel on drums, Greg Richling on bass and Patrick Warren on Chamberlin.

Jim Gable directed a black-and-white video set in a recording studio, with Apple at the piano and singing into a microphone in headphones. The song reached 34 on the Alternative Songs chart and 32 on the Adult Pop Songs chart. Steven Mirkin of Entertainment Weekly gave it an A minus and heard slurred, smoky vocals above a gospel-tinged piano, making it sound like Nina Simone covering early Elton John. Apple performed it on Saturday Night Live in its 22nd season and on MTV Unplugged.