The Black Rider

The songs were written for The Black Rider, a play directed by Robert Wilson and co-written with William S. Burroughs. It is based on Johann August Apel's story The Fatal Marksman, and Burroughs said he compared the magic bullet in the original German story to heroin. Allen Ginsberg suggested approaching Burroughs, and Waits traveled to Hamburg in May 1989 to begin work. The play premiered at the Thalia Theater in Hamburg on 31 March 1990.

Waits wrote the lyrics except for That's the Way, Flash Pan Hunter and Crossroads, which are credited to Burroughs. Burroughs also performs 'T'Ain't No Sin, a standard by Walter Donaldson and Edgar Leslie. Burroughs said he compared the magic bullet to heroin, and Waits answered that the first one is always free. Part of the album was recorded in Hamburg in 1989 by Gerd Bessler and part in 1993 by Tchad Blake at Prairie Sun, with Greg Cohen as musical director and Biff Dawes mixing at Sunset Sound Factory.

Lorraine Ari gave it four stars in Rolling Stone and Chris Willman three out of four in the Los Angeles Times. Will Pinfold wrote in Spectrum Culture that it is probably the most extreme album in Waits's output, and singled out November, which opens with a bowed saw.