If you like to listen to complete albums, but cannot fit your entire library on your iPod, create a Smart Playlist that contains a random selection of entire albums.
First, in iTunes, turn on Shuffle with the Controls » Shuffle » Turn on Shuffle menu item. Select the Shuffle menu again, and check Shuffle by Album. Next, create a new Smart Playlist with these conditions:
- Match the Rule 'Media Kind' is 'Music'
- Limit to 7GB selected by random (i.e. for an 8GB iPod)
- Check 'Live Updating' to update the Random Album Playlist by selecting and deleting albums in the Playlist
[
robg adds: While this clearly works, the disadvantage is that iTunes is set to random play by albums in normal use as well. I'd be interested in finding a method of creating a random-by-album playlist while maintaining random-by-track standard iTunes playback, instead of having to remember to toggle the shuffle order manually each time.]