Might the iRiver clix be the first Portable Windows Media Player to not suck? It's very possible.
$200 for 2Gig, the same price as the 2gig iPod Nano, but this one does movies and has a 2.2 inch screen and has an FM tuner (nice for NPR) and a voice recorder. Wallpaper to the right.
Just in case you have one and want to know what makes it tick, here's how to take yours apart.
Anyone have one of these bad boys who also had an iPod? It's calling me. Sounds like something Omar would like, but he went for a Philips GoGear with 6 gigs for $180.