I've been having a lot of fun with this one- smart playlists for the years I went to high school and college. Mine are two separate lists, but I suppose you could combine them.
Create a smart playlist:
Match - All
Year - is in the range - start year to end year
My Rating - is in the range - *** to *****
It truly is amazing how the music can bring you back.
I thought about limiting this only to tracks from my cd collection, but the extra tracks are a great addition. You'll undoubtedly notice "best of" and "greatest hits" collections from other years appearing in your date ranges, but in my case I decided to leave them be. I did listen to those collections, even though they are earlier works.