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I don't think you can do this on the console versions of the game. As i recall, on the pc version there was just a program which would randomly rename all your .mp3 files such that it formed a random order, because the game just plays the soundtracks sequentially from A->Z; so it all depends on file name. If you want to randomize it, you'd hvae to change the actual file names so they're out of alphabetical order. I am pretty sure this is still the case but i haven't played the game for a few years now....
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