My standard fall back playlist on my ipod/itunes is the Top 100 Most Played smart playlist that comes standard with iTunes. It’s music I enjoy, obviously, and it has enough of a mix of moods and genres that I can always find something I like. The problem is though, that the more I listen to that playlist, the farther and farther away those tracks become (in play count) from the rest of my library. Which then renders the list pretty static (read: boring).
New solution… the “after top 100″ playlist.
Basically it’s the same structure as the Top 100 (playcount > 0 and selected by most often played), but you add the exclusion of the Top 100 playlist. I increased the item number to 250 to give it more variety. Over time, listening to this list will eventually shift the songs up into the Top 100, bringing some of those songs down. Alternating the two lists should keep the groups near each other play count-wise. Might need a third tier playlist also, with exclusions of the two previous playlists eventually.