I'm fascinated by watching these Tom Waits interviews with David Letterman, with various available clips spanning 20 years. They both look like they're having loads of fun whenever they get together. Hell, you could put together a nightly show with just the two of them (it'd be funny enough, but of course it would ruin the mystery Waits has built up over the years).
Throughout, there's this sort of comfortable charm between the two. Letterman plays the straight man, patiently goading Waits into answers he knows will be ludicrous. But Letterman obviously knows how much he's being put on and doesn't even try to conceal how funny he thinks the whole thing is. And Waits is just bursting to let loose with ridiculous answers and strange yarns. It's really an act more than an interview.
Taken together, these clips form an insightful and compelling overview of Waits' music and persona. He's at turns rough and wise, a jester and a showman, and all along Letterman keeps poking around for something weirder and funnier from his guest. I'm sure they know each other fairly well by now and I don't doubt that private conversations are any less hilarious.
First up is a 1983 interview, with Waits pushing Frank's Wild Years:
Next is Rain Dogs era Waits, in 1986:
"Straight from the Top," in 1988, and another top-notch interview:
And next we'll jump forward to 2002, with Waits playing "All the World is Green" on his promo push for Alice and Blood Money:
And then we reach the near-present, with Tom visiting Dave once again, in 2006:
Tom Waits - A Christmas Card From A Hooker In Minneapolis (live Austin City Limits, 1978)