The Dark iTunes Library


  1. I found myself listening to the same music over and over again.
  2. I have over 37k tracks in my iTunes library and I’ve probably never heard most of them. In fact, when I started this, I had about 32k tracks with a play count of 0.

Possible solutions:

  1. Force myself to listen to specific artists and/or albums that I don’t normally think of playing. This requires actively perusing my library for such music, and I’m unlikely to waste the time on it.
  2. Listen to the entire library, A-Z. This would take over 100 days of listening 24 hours a day, seven days a week, and I’d get bored very quickly with listening to album after album of the same artist.
  3. Shuffle the entire library. Not a bad idea, but I can’t fit my entire library on my 16 GB iPhone.

My solution:

  1. Create a new Smart Playlist with the following rules:
    1. Plays is 0
    2. Skips is 0 – to keep this playlist from getting log-jammed with songs that I had started to listen to, then got bored or annoyed and hit the “Next” button.
    3. Media Kind is Music
    4. Genre is not Classical
    5. Genre is not Spoken Word
    6. Genre is not Children’s
    7. Genre is not Holiday
    8. Limit to 1000 items selected by random
    9. Live updating


  1. IncludeInclude this playlist in the playlists that are synchronized to my iPhone.
  2. Listen to this playlist. A lot.

Perfect. If the track is so boring or annoying that I skip it, it’s off the list.

Obvious question: why the hate for classical? It’s not that I hate classical music. It’s just that classical music really shouldn’t be shuffled. At the very least it should be consumed a movement at a time.

This is working really, really well. I always have different music to listen to on my commute, while running or while working. I’m down to just over 24k tracks that I’ve never played and I’ve found some great stuff hidden in the depths of my music library. I’ve also found some amazingly bad stuff, so I created another Smart Playlist: “Apparently I hate this shit.”


It pretty much just identifies that tracks that I skip as soon as they start playing so I can keep track of what I don’t like. There are less than 60 tracks in there so far; too early to see any real patterns.

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