I have about 10 gigs of music I ripped from my own CDs. WMPlayer does it natively or there are lots of freeware programs you can download.

OP, the first question is whether you want an iPod "equivalent" meaning that you can WATCH things on it as well. If so, your choices are a bit more limited and your battery life will suck.

If all you want is a music player, not a viewer, here's a third (or fourth, I've lost count) thumbs up for the Sansa clip. They start around $40 and work very well. They also record (which can come in handy for some things) and will broadcast FM stations. The micro-sd cards are really cheap now so you can sort your music into libraries by simply using more cards (2GB ones are dirt cheap now), and you can use one of the full-size adapters to just copy music from your laptop to the cards, then insert them in the clip.

The only downside is that it has an internal battery and is charged off of the mini-usb port. A generic phone charger will charge it as well (I use one from my old Razr).

Good luck.