I use Musicmatch Jukebox on my Windows machine. Like a lot of programs, it comes in the "Basic" and the "Plus" versions. Basic is fine, but gives you a mildly irritating "please upgrade" screen whenever you exit. Plus costs $20, and has a few more features. FWIW, MusicMatch is the software Apple gives you with the iPod for Windows (iTunes is only on the Mac). Get it at www.musicmatch.com.