It has been mentioned on other sites that iPod’s aren’t very random in their shuffling. I have lots of problems with my iTunes not playing songs that I want to listen to for days and days. I’ll be lucky to hear a song I *really* like once every month. I’ve created a playlist to get around this by doing the following:
- Create a new Smarty Playlist
- Put one of the criteria as “Last Played”, “is not in the last” X and “days” (I put 10 in for days)
- Add a “My Rating” criteria (I used greater than 2 stars)
Now you have a list of songs you haven’t heard played in the last 10 days that you have rated highly. The songs pop off this list as you play them so it will eventually exhaust itself.