Have been familiar with Waits since the ’80s & a diehard Tom Waits You gotta help me keep the devil way down in the hole shirt fan since the ’90s. Right off the bat, I’d have to say that trying to get into him is entirely the wrong approach. He’s one of those artists who you either get or don’t get. Those who get Tom are a rare breed. In answer to your question, though, Tom’s repertoire needs to be broken up into periods. How similar, really, is Small Change to Swordfishtrombones, for example? Or Heartattack and Vine to Mule Variations? Or even live albums like Nighthawks at the Diner to Big Time? I’d recommend taking one album from each period. Blue Valentine is pretty accessible for the ’70s, for example.
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As is Rain Dogs for the ’80s, Bone Machine for the ’90s. Tom Waits You gotta help me keep the devil way down in the hole shirt These are the ones I’ve loaned out over the years. Pay attention to the evolution of the music, the changes in technique. Then listen to the two live albums I mentioned in the previous paragraph & pay attention to the evolution of the performer and the man himself. When you’re ready to move on, I’d say listen to his whole discography in chronological order. And if you’re lucky enough to find them, watch videos of his live performance. I have Big Time, as well as recordings of his Austin City Limits & VH1 Storytellers performances. They are one of the few reasons I still have a working VCR.