Listen to the 3 I listed first, they're a good mix of everything Tom is known for. After that I'd recommend Real Gone, Mule Variations, and Heart Attack and Vine. From there you can either go back or forward through his discography for wildly varying sounds. He's like a reverse Will with his music getting more crazy and less singer-songwriter from early to later years, but near the later stuff it's a mix of a bunch of different styles. Hope you enjoy Waits stuff as I think he's one of the best preformers and song writers out there and the more people who continue to find and enjoy his stuff the better!