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It may sound corny and cliche, but my music collection is the soundtrack of my life. Certain songs are strongly connected with certain times of my life.
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Same here. I know full well that some of the music on my nano's regular rotation were goofy as all get out when I first heard them, and still are today (I'm looking at you, Sigue Sigue Sputnik) but they were what was on at certain good times in my life.
I can discover new music without having to pay every month for the privilege, thanks to niche music blogs, Vevo and YouTube. I'd rather have the money I spend go directly to the artists I like, rather than to a service who splits the proceeds so razor thin that only the top acts get any sizeable revenue.