Sorry to interrupt all this DMB talk, but no one has mentioned my favorite: Jimmy Buffett!
I am a *HUGE* Jimmy Buffett fan. I'll go for weeks where its all I listen to. I've only seen one of his shows live but it was amazing. If you haven't heard much of his stuff other than Margaritaville or Cheeseburger in Paradise, you're missing out on a lot. He's a great songwriter, and some of his best songs are not his big hits.
As for someone who I don't understand their popularity, I'd go with Eminem. I don't think he's talented, I think he's just violent and messed up. He portrays a really bad image and sets a very bad example to people, especially with his attitude towards women.
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