Letterman: Tom Waits

Before I knew anything about Tom Waits, I knew Dave was a massive fan. Waits has appeared on one or the other of Letterman’s shows ten times. It wasn’t until I saw Down By LawJim Jarmusch’s pulp fiction, jail break picture starring Waits, that I understood Dave’s fascination. From watching Jarmusch’s black-and-white, soupy bayou yarn about three escaped convicts, I could tell implicitly why Dave did everything he could for Tom. For Waits, like Dave, is this somewhat reclusive, creative, punkish American everyman, able to speak to the people of his time by needling together all that has come before, occasionally paying homage, but most of the time poking at it for effect. Here, I have compiled all-but-one of the ten known appearances available, with a sprinkling of notes on certain performances. Come for the music, stay for the interviews.

Tonight, Waits waves goodbye performing a new tune for Dave. According to his site, “I don’t know when I will see Dave again. I guess from now on we’ll have to settle for bumping into each other at pilates.”




10/05/88 (Minute 21:00)

1999, “Chocolate Jesus,” arguably his best and most famous performance on Letterman, this YouTube clip has well over seven million views, and for good reason.




09/07/2012, the interview, in which he said, “You know what was new, was jogging was new…. I thought it was an acronym: Jamaicans On Grass, or something.” And then he shows-and-tells a 19th Century contraption he bought in a music store.


We almost had twelve Waits performances for Letterman. According to a former NBC page who called into WNYC’s The Brian Lehrer Show on April 7, 2014 (minute 9:10), Waits was scheduled to perform “Romeo Is Bleeding” on The Tonight Show on a night when Dave was filling in for Johnny Carson, but Waits inadvertently sang an obscenity and wasn’t allowed to continue with his performance.

I must give a big hat tip to the folks behind Open Culture for alerting me to this unparalleled American television tradition.