Way back in the day (c. 1988) I started making mix tapes. Now, I realize that these days, a mix of songs on Spotify can be called a mix tape, but I’m talking about the kind of thing that only magnetism and spinning spools can do. Real tapes had restrictions in the way that digital mix tapes don’t, particularly with regard to length. I used 90-minute tapes; that’s 45 minutes per side. Likely, and not by coincidence, vinyl LP records maxed out at 45 minutes as well. I would carefully time each song and come up with thematic combinations that optimized the 45-mintue duration. Not surprisingly, a mix could take hours to construct and record. It was meticulous work. In the 90s, making mixes from CDs, I had a mix tape called “Girls, Girls, Girls” which proved enormously popular among my university classmates’ walkmans, and featured great female artists or female-fronted bands like Frente, Tori Amos, Sarah McLachlan, and Garbage.

Fast forward to c.2005 when I got my first iPod. A 2nd-generation iPod mini, to be exact, with a massive 4 gigabytes of storage, enough to hold 1,000 songs. At first, I put a bunch of random songs and manually created playlists on the iPod, all managed through Apple’s free iTunes software. Today, I have a an iPod Classic with 160 gigabyte capacity that literally holds my entire music library (10,560 songs as of today, November 5, 2017).

Getting smart about my playlists

A short while after using my iPod Mini, I discovered smart playlists in iTunes. These playlists are dynamically created based on criteria that I specify. My mind immediately went back to creating 90-minute mixes, but they could be constantly changing and updating themselves.

The keys to creating my smart playlists are:

• rating each song, and
• using the “comments” field to group them in meaningful ways.

The auto-populated “genre” field is largely useless as a criteria. I don’t care that the powers that be determine Sarah McLachlan as “adult contemporary” or “pop” or “rock” depending on the album; I want to tag my favourite Sarah McLachlan songs as “girls” and “Canadian” and “90s pop” for example (using the “comments” field).

As for rating songs, I use the following guidelines:

• 1 star: I don’t want this song showing up in my smart playlists
• 2 star: mediocre songs, I don’t need to hear these too often
• 3 star: pretty good songs
• 4 star: excellent songs, I want to hear these fairly often
• 5 star: my absolutely favourite songs; these can make it into many smart playlists and I won’t mind

Suffice to say, most songs are rated 3 or 4 stars.

Building the smart playlists

Once I had most of my songs rated and commented, it was time to start building smart playlists grouped by tags in the “comments” field of songs. A few of my first smart playlists included:

I want to include mostly my favourite songs and fewer of my less liked songs. Since I’m thinking in terms of 90-minutes mixes, I limit my smart playlists to 20 songs (90 minutes, or one tape) or 40 songs (180 minutes, or two tapes). The math works out pretty nicely. For example, my 40-song smart playlist for 80s pop includes:

• 16 songs rated 5-star, with comment “80s pop”
• 12 songs rated 4- star, with comment “80s pop”
• 8 songs rated 3-star, with comment “80s pop”, and
• 4 songs rated 2-star, with comment “80s pop”

The lists are filled with the least recently played songs. This point is crucial. This means that every time the smart playlist refreshes, it automatically picks songs I haven’t heard in a while. Basically, over time, I get to hear ALL the songs I’ve tagged as 80s pop, while mostly hearing my favourites.

Here is my smart playlist settings for the 80s pop songs, one “auxiliary” playlist for each star rating:

The auxiliary playlists are used to build a master playlist; they are never played individually. The master 80s pop playlist is set as follows:

Reusable Method

This method is reusable for any number of criteria. I’ve created many other dynamic playlists that effectively shuffle through my entire library of songs. When I add more music, I only have to rate the songs and add tags in the comments fields to make sure they find their way to the dynamic lists. The rest takes care of itself. The “Live updating” check box in the smart playlist settings makes sure the list is always reconstructed every time it is played. With my iPod classic, I have to plug it in and sync it before the lists are updated on the iPod.

The list of choices for criteria in iTunes is very long; you can base the smart playlists on just about anything. For example, I have a list called “Best of the Year” which looks like this:

And I had to create my own “Shuffle Songs” playlist, because the one built into iTunes would pick random weird stuff like old podcast episodes, songs rated 1-star, or classical music, which don’t work in my typical lists of more popular music. Here’s my customized “Shuffle Songs”

The biggest advantages to using a geeked-out system like this is rotating through your entire music library and hearing songs you haven’t heard in a long while. It does take some effort and time to get it setup, but then it’s only a matter of rating your new music and putting some tags in the comment field.

Happy listening, and please comment below if you find this method useful, or if you have other cool (or geeky) ways of listening to your music.