I have a music playlist program which deals with the problem of getting used to music. It's effective because I seldom want to choose a track to play, and I don't find myself skipping a lot consecutively.
I have a dedicated key for skipping (and I keep adding meta keys to make it skip more (each meta key is x2)). The next track to play is automatically selected based on the combination of two factors: being skipped less and being played less.
I get to hear my whole collection in a way that's far more enjoyable than an unweighted shuffle.