So after trying both the ipod and Zune I would say the ipod beats it by a longshot. I am not even talking about the whole DRM issue. It is so hard to just get the Zune to have exactly what I want on it. It continually tried to put my entire hard drive on it even though I kept telling it to not automatically sync. Just to get the thing up and running with a limited number of songs took a WHILE. In half that time, when I first got my ipod, I had already put every song I wanted on it, a few videos, and was already listening to it for a decent amount of time. So if you're paying the same price for them ($135 aint bad for it, and I got my Zune for free or else I would never have one) oh god just get the ipod.