722 Views 1 Reply Latest reply: May 12, 2010 5:14 PM by rockmyplimsoul
Is this a smart playlist? If so, it could be related to the known bug where a playlist's content and sort order don't match iTunes. There is a workaround for that though, just edit the playlist by adding the criteria "Playlist Is Music", where "Music" is the general category in iTunes for music items.
If that's not it, it could be that some of your songs are tagged as "Skip when shuffling", so when your iPod is in shuffle mode they won't show up in the playlist.