I've always objected to people who listen to music for the wrong reasons. Be it fashionable that week, all of your friends like it, the manufactured VJ tells you to like it, etc. All of these reasons, are not true reasons to appreciate music. Music should speak to you on a very primal, emotional level. If a certain song or artist appeals to you and affects you, my advice is to remove that artist from any social stigma/misconceptions or perceptions of the artist or song that you already may have. Evaluate the song yourself: do your own thinking. Just because a song never became a hit, doesn't mean it is a song of poor quality, and, in turn, just because a song became a hit, doesn't mean it is of poor quality.
This being said, I was, at first, admittedly hesitant to start to "get into" Mr. Tom Waits. Any music that is said to be hip and/or fashionable to listen to, I immediately have a bit of premonition to explore. Don't make the same mistake I did. If you're a fan of true, honest songwriters, you may already be a fan of Tom Waits and not know it. His songs are so painstakingly real that they are, at times, difficult to listen to, which makes them all the more rewarding and endearing in the end. His work is so varied and challenging (especially the Island Records years) that it often takes patience, but stick with him: you'll be glad you did. If I were to recommend a starting point, I'd probably recommend the same Waits album that I started with, his melancholic debut album Closing Time, from his more melodic, jazzy earlier years. I discovered each album after that one chronologically, which, if you enjoy Closing Time, will ultimately prove extremely rewarding. For any emotion you may have, there will be a Tom Waits song that you will think he wrote especially for you. Or a hooker in Minneapolis. Or a mule. Or Rickie Lee Jones. Or Christ.
Plus, there are few better companions on a clear, June night, than Mr. Waits and a bottle of cheap red wine.
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