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Have you ever had the experience of putting on an old record and thinking, "Wow, I had forgotten how good this was!"?
I'm having that experience right now with Fumbling Toward Ecstasy.
Of course, if you have all your music on a server playing a shuffle, I suppose you are enjoying your personal Muzak, but there are experiences that you are not having.
I think that, not every time but often, there seems to be a rough inverse relationship between quality of experience and convenience. A Quarter-Pounder is convenient, a can of soup is convenient, but they might not be the yummiest foods that you can experience. An automatic transmission is convenient, but doesn't it make driving kind of boring? mp3s are convenient, but they aren't hi-fi. And a stack of them randomly playing can be a very mundane experience. Sex is certainly nice, but romance is bigger and scarier and much more beautiful.