Hello, I'm trying to do a clean up of my massive iTunes library and I'm using a smart playlist to help. Here's what I've got: Media kind is music Last skipped not in the last month Last played not in the last month This way I can just put the playlist on shuffle and if there's a song I don't like I just rate it as 1 star. I then remove all the 1 starred songs from my library later. In theory I'd like to be able to have the song disappear from the playlist if it's either played or skipped. With this currently playlist though it only disappears if it's been played. If the song has been skipped then it stays in the playlist. I'm skipping past way more songs than I'm playing since my goal is to sort the music as fast as possible. But I am listening to the playlist while I'm doing other work so sometimes I let the entire song play, especially if it's good. The problem has to be with having both last skipped and last played at the same time so is there any way to have the song automatically removed from the play list if it's either been skipped once in the last month or played once in the last month? Thanks in advance for any help.