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A few things from the posts above I don't quite agree with: a) I wouldn't call Tom Waits a talentless hack, but I would say he is very fake. Whether that's a bad thing depends on how you take it. I don't think he intends to deceive anyone. I just think he loves the aesthetic of smokey old jazz of a particular kind, so he tries to evoke that kind of vibe. His vocal style and voice is obviously 100% affected, so it's really up to how you take it as a listener. Is he successfully evoking a style or is he unintentionally parodying it? You be the judge.
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Well said. Fantastic retort.
The problem with him, and I've said this before, besides the one song, Heart of a Saturday Night, he completely lacks substance. Everything about him. His voice, his song structures, the percussion he uses, and especially posing as somehow experimental or avant garde. Nothing about him is sincere, not even his falseness. He's hollow. Fool's gold. All facade.