Ever since I got my 60 Gb iPod for Christmas, I’ve been using iTunes as my music player when I’m on my computer (XP Pro, sp1). Overall, I’m very pleased with it, but there’s one thing that has really been frustrating me, and that’s the failure of a “smart” playlist when used with Party Shuffle.

I have lots of music. 12,701 songs, to be precise. With a library that large, it’s easy to forget about entire albums, so I have setup a playlist that I call “Never Played” that is supposed to only return songs that I’ve never listened to through iTunes. The definition of this playlist looks like this

Given that definition, one would expect this “smart” playlist to only return songs with a play count of 0, that do not have a genre of classical or musical (as in Sondheim, Webber, etc). I use this playlist via Party Shuffle like so

How, then, do you explain this? Notice the line that I’ve highlighted with a red box. The final column on the right is the play count column. This should always be empty when using this playlist until after the song plays.

This happens at least once a day, and usually more frequently. If I change Party Shuffle to use a different playlist and then switch it back to “Never Played,” the duplicate will be gone and things will work properly for a while. Then another already-played song will show up in the list. I’ve even noticed a few times that as soon as a song has rolled off the top of the list it will roll back on to the bottom, complete with a 1 in its play count field…

I update to the latest iTunes every time there’s a release, but it still happens. I can’t imagine that I’m doing something wrong, but you never know. Ideas, anyone?