One of the great features that iTunes and the iPod brought to music listening was the ability to shuffle your entire music library, or simply the contents of a playlist. But you may not always want to listen to songs; you may like listening to albums.
Well, iTunes can do that too; you can shuffle albums. If you select Controls > Shuffle > Albums, then Controls > Shuffle > On, and start playing an album, iTunes will play that album to the end, then start another album selected at random.
This is great if you want to have music playing for a long time, and don’t want to intervene.
Unfortunately, there seem to be some bugs with this. It doesn’t work in all of iTunes’ views; it doesn’t work when you’re viewing a playlist, for example. However, if you choose Artists, Albums, or Genres in the sidebar, then click the Play button, it seems to work.
Another option is to use Doug Adams’ Play Random Album AppleScript. Run this script, and it starts playing an album, until it gets to the end. If you don’t like the choice, just run the script again. And when the album ends, run the script again to play another album.