Quote Originally Posted by Shinysides View Post
iTunes sucks.

Yeah but seriously, sorry I don't have an answer beyond expressing my dislike of iTunes. If I think of something I'll let you know. Did you try adding the music to your ipod via Winamp?
Lol, this was pretty much what my response was going to be.

But anyway, if the song is in your library, you can do this. On the left sidebar, drag the library icon down to your iPod's icon. That should sync up your iPod's library with your computer's library.