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Where do I begin folks?
then Mule Variations. Then probably Nighthawks at the Diner. Small Change and Closing time are a bit easier listening.
Maybe Blue Valentine or The Heart of Saturday Night.
After listening to those, you'll have a pretty well-rounded view of his work. From there, if you like him and want to hear more, you can go in whichever direction you'd like.
Swordfishtrombones and Bone Machine are essential listening in the same vein as Rain Dogs or Mule Variations. Small Change and Closing Time are in line with The Heart and Blue Valentine.
Really though, everything is great. I do love his post-2000 work.
It's really cool to hear how he develops...