Advanced iTunes playlists

Learn how to effectively use playlists using Boolean algebra

Dave Sag
Mac O’Clock

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iTunes — The Jira¹ of music players.

I don’t do streaming music services. When everyone in the office is steaming their Spotify and Apple Music collections it reduces the bandwidth left for actual work to a trickle. Also, I have read that artists themselves get royally screwed by streaming music services.

Abba Arrival: An awesome album cover

I’ve been collecting music since I first bought Abba Arrival back in 1977. I have over 1,500 albums in my iTunes library and have curated the star ratings carefully ever since I started using SoundJam in 1999 to load tunes into my Rio One. When Apple bought SoundJam and subsequently released iTunes I moved over to that and, for better or worse, it’s been my default music player ever since.

People love to complain about iTunes, and there are many reasons to do so, but for all its faults, it remains the best of a bad lot. In particular, people seem to moan about playlists; something I have never had an issue with. So I thought I’d demonstrate how I configure smart playlists.

Smart Playlists simple boolean algebra

Smart Playlists support both and and or conditionals. Because these are hidden away, however, most people have no idea they are there, and even fewer have any idea how to use them. So people write-off Smart Playlists as gimmicks but they are actually very powerful.

An example

While I work I want to hear songs by a specific set of artists that I have rated higher than 3 ⭐️, that I know is kept in my iCloud collection (so it can be played off my iPhone, or laptop as well as the iMac in my office), but which I’ve not heard in the last 3 weeks.

Example 1: Music to work by — music by selected bands I’ve not heard in 3 weeks

Another example

Every once in a while the overflowing piles of old receipts and other detritus reach a breaking point in my office and I need to clean it up.

For those times I want music that’s a bit more distracting. It’s still got to have been rated more than 3 ⭐️, I still want to be able to play it from any of my devices, the songs should be shorter ones, and I should not have heard it in the last 7 days. The artist list is a bit more poppy.

Example 2: Music to tidy my office by — shorter songs by selected bands I’ve not heard in the last week

A more complex example

I love the Late Night Tales series of records and have bought almost all of them over the years. This playlist will reliably play all the music of the Late Night Tales, or Another Late Night series, except for the spoken word tracks that conclude each record, whose rating is greater than 2 ⭐️, or I’ve clicked the ♡.

Example 3: Late Night Tales —Just the music that I actually like.

How do you insert those indented conditions?

Hold down the option key and it changes the + to a , allowing you to inject an any/all sub-clause.

Here’s a nice tutorial on basic boolean algebra if these playlists seem confusing to you.

Enjoy.

¹ Jira, by Atlassian, is arguably the world’s best software for managing software projects, but as anyone who’s actually used it knows, it’s horrible to use. Plenty of people have tried to make better tools but no-one has yet succeeded. So too with iTunes. Sure it’s a nasty old piece of bloatware, but it’s still the best there is at what it does.

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