Smart Playlist hacking in iTunes
I really enjoy having my iPod on while I work. I have ecliptic music tastes (my wife says “random” but whatever). I actually don’t mind having songs go from Chris Rice to The Faint and then to Tom T. Hall. No, really, that’s just fine with me.
The problem was getting the right random mix. Not with songs in my iTunes that I don’t like, but I do want to hear songs that I just imported into iTunes. And I want a fresh variety every time I sync my iPod with iTunes. Tall order? Nope, not really — not with a little knowledge about Smart Playlists and a little initial work.
I wish I can say I came up with all this on my own — but I didn’t. The direct inspiration for this process came from Andy Budd, who has a much longer and more detailed explanation. I am just giving you my version of his work. 
The concept is simple — build a series of utility playlists to “filter” the music into one playlist. Each utiliy playlist has only one operation. This keeps each operation simple, but the end result is quite complex. I named each of my utility Smart Playlists with “zzz” to keep them at the bottom of my list of playlists — that way it’s hard for me to accidently change it or remove it.
The first thing to do is to create a base playlist where all the other playlists will be based off of. I do this because there are files that I don’t want on my iPod unless I specifically say that I want them — like Christmas songs, podcasts, etc. The following screenshot shows my base playlist, called zzzAbase.
The next playlist is an easy one — I want songs that I haven’t listened to in a while. In my example, I said in the last two weeks, but this amount will depend on how much you like something more refreshed, etc. Now that the song has to be in zzzAbase to be included.
The next playlist is pretty simple — it puts in my highest rated songs. This does mean I rate them. I try really hard to rate each song (especially if I really like it or if I really don’t like it) but I don’t always do it when I’m deep into work. That said, I think that this an important list.
The next playlist is someone cryptic in meaning. This just means “pick any ol’ song out of zzzAbase and put in the playlist”. This will make things a little more random (and interesting). I keep the total number of random songs to fifty, which gives it less weight than the rest of the playlists.
The last playlist is the one that I sync to — aptly named sync. I just say “grab songs from any of my other playlists.” Note that zzzAbase is not mentioned. That is the superset of sync but gets “filtered” by the other smart playlists that I have setup.
As you can see, I have other playlists that I sync to. You can figure out what they do. I won’t show how I did it here — I leave that as an exercise for the reader.
After that, just play your iTunes in your sync playlist or just sync your iPod to it! Then you have a nice, ever changing mix of music at your command.