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I have always played a lot of music. I had hundreds of tapes and CDs back in the days of physical media. Like everyone else, I've switched to streaming, but I've found a real problem with streaming: I forget acts that I liked. The cognitive load of recalling my discoveries has stymied me.

Recordings I played a bunch of times for a week or two in 2023 haunt me today. I feel bad having forgotten them, and I know in many cases my fandom would deepen if I just played them a bunch more times and it really clicked.

But other than hoping Apples shuffle algorithm will resurface them when I happen to be really paying attention, I haven't known quite what do do about this problem.

Enter AI.

Last week, I requested my complete musical listening history from Apple Music, and it finally showed up this morning. Once I had that, I decided to dig around in my files and also pull out my old iTunes listening history from when we owned music. 

I dumped all that into ChatGPT and I've been playing around with that data all day. One thing I asked it for was to give me a list of my most played songs, but with only the one most played song by my most played artists. So, like, I listen to The Decemberists a ton, but it's only on here once. The song by them that got the most plays over my history.

Looking at this list is like looking at a third-order autobiography that's only legible to me. 

On the list below, tracks are shown ranked from the most played to last. The first two are giant outliers. I got obsessed with Ferreira's cover of this classic song by Commodores in 2019. I was literally playing it on repeat, which I never do. It was strange. 

I still like it, but I don't just lay there playing it over and over like I did that year. 

So here's the list. If you happen to be an Apple Music user and this looks good to you, the playlist can be found here as well:

I also strangely got a bit fixated on "Crave You" by Robinson for a bit in 2017. Not sure why, but it is a good song. 

What I like about this list is I can look at it and see acts that I tend to play whole albums at a time and then specfic tracks I seek out, or have on playlist. 

One of my favorite playists, which is probably evident from this list, is a list of covers by more recent acts doing great songs from like the 70s and 80s. There's been a lot of great reinventions in the last decade. Love to hear the kids digging on the classics. 

Something about scanning this list makes me feel whole. Music has been a big part of my life. Apparently Apple Music has me playing over 15,000 artists and more than 80,000 different tracks. There's a lot of stuff I keep coming back to, but I wander widely.

I didn't put the counts on here, but my most played song, "Easy," I've played 250 times. My least played ones on here are tied at 50 each. I don't think these are very big numbers in terms of repeats for most people. I think I wander more widely than I return.

That said, my core is the ladies of indie rock, 80s and 90s rock classics, psychedelic with a smattering of metal and instrumentals and country. ChatGPT says I like atmospherics and distinct characters. 

One other fun thing I did with all this data: I asked ChatGPT to make me playlist with 333 songs on it by 333 acts I've never played before, but that it thinks I would like (based on this data). I've been playing that the last couple hours and I've found some awesome new stuff. 

So many talented people out there doing cool stuff. It's amazing it's only a click away.

And, yes, my favorite Beatles song is one of George's. 

—Brady Dale
November 1, 2026

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