The ongoing quagmire that is iTunes Catalina

So, the latest issue with iTunes is that for whatever reason it’s stopped letting me actually play in a shuffle-from-library way. Which is to say, they got rid of the view where you can just see your whole library as the library, and click a “play” or “shuffle” button from there. I don’t know when it disappeared, but I know it used to be there, and now it isn’t.

It used to be that if you just had your view set to “albums” and pressed play anyway, it’d go ahead and choose something at random to play. But today it just kept on doing the same album: The Bends by Radiohead. Which is, granted, a great album, but I don’t know why it was choosing that one and that one alone, and I only felt like listening to it once, you know?

I used to sync to my iPhone using smart playlists, but that stopped working correctly; even if USB sync were still working (I never did get that solved), the playlists themselves are no longer respecting the shuffle-by-album setting, on desktop or on the iPhone. So I’ve been using Smart Shuffle and iCloud Music Library (via iTunes Match) to do my iPhone shuffling as of late.

But my old selection smart playlists are still useful for playing music on my computer. First, here’s how I have it set up:

iTunes "entropy source" playlist

Create a new playlist, and set it to Match music for all of the following rules:

  • Media Kind is Music
  • Last Played not in the last 3 months
  • Last Skipped not in the last 1 weeks
  • (other rules go here)
  • Limit to 9999 GB selected by album
  • Live updating

And then when you want to actually play music, make sure your “shuffle” is set to “by album” and then right-click the playlist to select its “shuffle” option (or you can normal-click the playlist and then click the “shuffle” button in the player controls above).

Now you’ll hopefully have music shuffling the way it is meant to be played!

With this method there’s no longer a playlist order that you can modify as you see fit, but you can still at least see what’s coming up and remove things you don’t want to listen to, by opening up the history sidebar:


Unfortunately this only lets you see as many items as will fit in the window and gives you no opportunity to scroll, for some reason. Thanks, Apple.

Also, I highly suspect that any songs that are not assigned to an album will show up as an “Unknown Album” album, although that’s nothing new. My workaround for that was to have a script that goes through all the “Unknown Album” songs and tag them with a suitable identifier; for example, Plaid/Unknown Album/New Family.mp3 gets tagged with an “album” of “Plaid - New Family (single)” or the like. Although that tends to uglify stuff a bunch too. It’s just really annoying to have the playlist get to some musician who put a bunch of singles online and to hear them all back-to-back, you know? Especially when they’re incredibly prolific… (And this gets extra-awful when it’s an mp3 which didn’t have any tag at all, so it becomes “Unknown Artist - Unknown Album - Track 07” or whatever. I sure have a lot of that stuff. Sigh.)


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