Woke on a Whaleheart is the first record released by Bill Callahan under his own name instead of his nom de plume Smog.

[6] A single, "Diamond Dancer," preceded the release of the album on March 20, 2007.

The arrangements of labelmate and former Royal Trux vocalist and guitarist Neil Michael Hagerty are featured on the album, and Callahan's band consists of vocalist Deani Pugh-Flemmings, guitarist Pete Denton, violinist Elizabeth Warren, percussionist Thor Harris, bassist Steve Bernal, and keyboard/lap steel player Howard Draper.

Woke on a Whaleheart's sound, according to Callahan, touches upon "gospel, tough pop and American Light Opera.

"[7] Joe Grillo of the art collective Dearraindrop created the album artwork.