Beginning with 1983’s Swordfishtrombones, listeners were introduced to a very different Tom Waits—one more likely to sing something resembling a sea shanty while bashing on junkyard trash than a piano ballad, as had been his style during the previous decade. So Letterman, in his second year on air, caught Waits at just the right time.
Waits walks out to Shaffer grooving on his trademark dated organ (a sound he’s stuck with through the decades) playing “Frank’s Wild Years.” It's a perfect choice, because to modern ears this song already sounds like a commercial break intro/outro on an old talk show. From there, Tom essays Frank’s fate just has he had on record, mining audience reactions and laughs missing from the studio recording.
During the interview between songs, Letterman has specific knowledge of Waits’ past, aware that he used to live at the Tropicana Motel on Santa Monica Boulevard and hang out somewhere called Duke’s Coffee Shop, where he kept his piano in the kitchen, and that he lived in a house trailer, as well as in his car—and even that he was born in a cab in Dave’s native Indiana.
After a commercial break, Waits floors the audience and viewers at home by reaching back just one album in his catalog, a wide gulf in his evolution as an artist, to “On The Nickel” off 1980’s Heartattack and Vine. Waits’ festive, reflective performance of the song proves that to whatever extent he was willing to smash form in his music, he knew where his strengths were.