"Shadowboxer" is a song written and performed by American alternative singer-songwriter Fiona Apple.

[4] Shot entirely in black-and-white, this takes place in a recording studio, with scenes of her playing the piano and in Fostex T20RP headphones singing in front of a microphone.

[6] It fared much better on the Adult Pop Songs, peaking at number 32 and spent over 15 weeks on the chart.

[7] Steven Mirkin of Entertainment Weekly gave the song an A−, he wrote, "Singing to a former lover, her slurred, smoky vocals float above a loping, gospel-tinged piano, vibes, and string arrangement, making her 'Shadowboxer' sound like Nina Simone covering early Elton John.

"[8] Stephen Thomas Erlewine of AllMusic described the song as "haunting", remarking that while "it strives to say something deep and important, much of the lyrics settle for clichés.