I have about 7,000 songs in my iTunes music collection and I've always been disappointed with the shuffle feature of iTunes; it seems to bring up only a small sample of those songs. I thought I'd share a Smart Playlist that I use to find the songs that I might have forgotten about.

If you haven't used Smart Playlists before here are Apple's instructions for creating a Smart Playlist. Once you create a new one you can configure it like I have below:

There are three rules:

1. Select everything that has only been played less than one time (i.e. never played).
2. Limit the selections to Music.
3. Skip any tracks that have been skipped more than twice.

I called this playlist 'Never Played' and used it to find a few hundred tracks that iTunes shuffle never played. As they were playing I put the ones I liked into other playlists, rated them or skipped them.

Of course you can adjust this playlist or make others like it to fit your needs. Once I've heard all the songs in my Library at least once I could edit this list and change the 'Plays is less than' to '2' and keep incrementing my way through my lesser heard tracks.

If you like to use stars/ratings to create playlists of your favorites you could create a Smart Playlist to find tracks played less than 5 times and not yet rated:

I hope this gives you some ideas for how to use Smart Playlists to explore your music collection!