I’ve listened to Triple J’s Hottest 100 countdown for decades. Long after I grew out of being the target demographic, I’ve enjoyed it as a small window into what’s popular just a little outside of mainstream, and I make an effort to listen to the entire countdown every year. This year I had a hashtag-proud-dad moment when my daughter heard a song playing and told me it was one of her favourites – I’d never heard of the artist! The song was quite listen-able, there’s hope for the kids!
There is, however, one thing that’s always bugged me about the Hottest 100: they put their playlists in the wrong order. If you go to listen to a previous Hottest 100, you’re going to be listening from #1 to #100, instead of in countdown order, as the gods of music democracy always intended.
Now, when I say it’s bugged me, I do need to clarify the level of annoyance: mild irritation on the odd occasion at most, certainly never enough to do anything about it. That is, until the current iteration of LLM-based coding agents have started to demonstrate a reasonable ability to one-shot moderately complex software. And so, I threw the problem at Claude, and it quickly popped out a basic working solution!

Claude’s solution certainly wasn’t perfect: it required a bit of lateral thinking to get it feature complete. Working with Apple Music, the MusicKit API doesn’t let you upload playlist cover art, but the Apple Music macOS app does. So, I got it to first collect all the cover art, then use a small AppleScript to upload the cover art to the playlist through the desktop app!
This is where I think LLM coding tools really show their strengths, and where I think the job of Software Engineer isn’t going away any time soon. They’re a great way to write software or features that otherwise wouldn’t be a high enough priority to be built, but they still need expert input to build the right thing. From a human perspective, clearly the playlists needed cover art, but Claude wrote it off as being too hard after trying to do it just with the MusicKit API. It needed someone to a) know that the Apple Music app could upload playlist art, and b) it’s possible to write an AppleScript to automate that. By definition, LLM-based tools deal in statistically likely connections, so they’re not going to come up with a lateral solution on their own.
If you’d like to run the tool yourself (noting that you’ll need an Apple Developer account), I’ve made the repository public here. If you’d just like to listen to old Hottest 100 playlists the way the gods of music intended, you should be able to see them on my profile, or search for “hottest 100 countdown” in the Apple Music app.

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