Tom Waits and Frank Zappa are the big ones for me. Both seem to be great people (seemed in Frank's case) who really had their heads on right when it comes to the music business and how the world works in general. Whenever I read interviews, hear them doing speeches, or just them talking in between songs during concerts they consistently impress me. There might be artists whose work I like more than theirs but they are the ones who I feel the most personal connection with and respect the most, and who I would most want to be like.
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