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What operating system? As far as LEGAL tunes go, I don't know of any software that'll help you. If you have mp3's of your own and you want to upload them, here's a few suggestions. If you're using linux, gtkpod will be your new best friend. As far as for Windows or OS X, I have absolutely no idea. Try googling for ipod hacks, i'm sure there's something good out there. Good luck!
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