Yep, big Waits fan here too, since way back. I think my introduction to him was Blue Valentine and I've been hooked ever since. He's never disappointed me, but certainly some recent work is more 'challenging' than previous work. Still, love all his work. His mastery of language is genius, and entirely unique. I'm particularly fond of the collaborations with his wife, Kathleen Brennan, especially, "SwordfishTrombone". For some reason I'm particulary drawn to his spoken works too. A recent favorite is "Circus" from RealGone (a great live version of which is on "Glitter and Doom" makes that album worth the investment - otherwise that album is very poor acoustically, but has some good live performances).
If I had to list three favorites they'd be, SwordfishTrombone, Small Change, and Rain Dogs.
There's some very good compilation collections: Used Songs, Beautiful Maladies, The Early Years, Orphans..., and The Asylum Years. For anyone unfamiliar with Waits one of these might be a good place to start...I'd go with Beautiful Maladies as that's pretty approachable and midway through his career (also some of my favorite stuff of what he's done).
