I was listening to "Way Down in the Hole" and I could spot from a mile away that he had Marc Ribot doing guitar on that. I love Marc Ribot. He worked with my favorite jazz group possibly ever, Lounge Lizards. If you've never listened to them and would like some recommendations I'd be happy to give some.
Both that song and the one before are definitely very art-house, as you put it. Those are apparently from the albums directly following Rain Dogs, so I'm thinking I should give those a listen.
I've definitely listened to the older stuff like Closing Time and while I remember it all being very nice, it certainly lacks the unique character of Waits' later stuff. Early Waits is the kind of music I might put on if I'm in the same mood I would be in if I wanted to listen to Bob Dylan (whom I also love).
Thanks, I appreciate these recommendations. I think I can see myself going on a bit of a Tom Waits kick after this.