Brandon Barker , and the more and more I mess with it, the more I love it. I have dabbled a little bit in creating smart playlists, but haven't come up with anything too dynamic.
Recently, though, I created a new smart playlist entitled "Long lost gems".

You can see several things. All of the songs haven't been played in the last three months. This can be tricky because I have a habit of being impatient and pushing "next" 5-10 seconds before the song is over, especially if it has a long outro. Next, I make sure that I haven't skipped the song in a while, assuming that if I have skipped it recently, I wouldn't really want to hear it that badly. I make sure that the play count is greater than five, hence the denotation as a "gem". Checking the "Live Updating" box at the bottom is nice because after I have listened to a song on the playlist, it is automatically removed and replaced with another song with the same critera.
For more suggestions regarding smart playlists, check out . If any of you have experimented with smart playlists, what are some of your better/favorite configurations?

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This has nothing to do with iTunes or playlists… but I miss you. I could use a friend to converse with.
Boolean operators are our friends.
I have a good one called “Good Singer Songwriter Types” – match any rules, with a list of about ten artists .. . .lets me define my own genres based on artists w/o using the predefined CDDB genres.
I don’t know what that list will lok like for me, but I copied it exactly. I just hope I don’t have any Dying Stars in it.
i copied your criteria exactly too. my new smart playlist only had 2 songs. well, i’ll take it. yeah, i’ll take it.