well, from what little I know of iPod's (and I try to know as little as possible, but I guess I'll leave the iPod bashing out of this post, haha), they want music in their own proprietary format. Proprietary format = DRM = they control how you listen to your music.
My guess is you plugged the iPod in, and dragged and dropped MP3's onto it via an Explorer window? yeah that won't work. What you've done is put data on there that it has no idea how to handle. It is essentially in solid state storage mode.
Most likely, you'll have to use iTunes to convert your music files into whatever format Apple likes (I think its AAC, but I really don't know).
What I would suggest though, is that you do not convert all your music to that and delete your MP3's, etc. iTunes stuff is all about the digital rights management, which basically removes all your rights to your music. Read the end user agreement VERY carefully, and they basically tell you they will do whatever they want to in the future as far as how you can play your music.
the future of digital audio and video is very scary with corporations and their DRM.
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