Tip of the fedora to Dan for this great idea.
Do you ever get tired of hearing the same music over and over again from your iTunes library? Here’s a possible cure.
Select all of the music in your music library. Right click on one of the highlighted items and select “Reset Plays” to make the play count for each item “0.” Create a smart playlist based on whatever criteria you want. As the final criteria, add Plays is 0. Click OK.
Now, once you have listened to an item in the playlist, it drops out of the playlist.
Dan syncs all of his music library to his iPod. Every time he listens to a song the play count goes to “1” for that song. When he re-syncs his iPod to his computer, that song drops out of the play list. At the end of the year, he starts over.
- Making the most of the iTunes Column Browser (macworld.com)