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I'm very set in my musical ways: I like purchasing single mp3s (or the equivalent), and then resorting to youtube rips if I have no other option. I've rated all my music ever since my iPod only had room for "3 stars and up", and then have good, better, best (3+ stars, 4+, and 5, respectively) smart playlists, and then try to listen to the "good" playlist (in reverse chronological order) daily, so I form a connection with the music. Anyway, Apple has a curious algorithm for assembling a thumbnail for a playlist, and mine has been consistent for a long while:

I think it's picking "A,B,C,D" so in my case, Ani "Buildings + Bridges" DiFranco, BPA ("Toe Jam" with David Byrne - fun sort of NSFW video for that), CAKE ("The Distance" was my senior solo), and Dar "Cool As I Am" Williams.