Over the past few months I’ve been taking a random stroll through what Rolling Stone magazine has determined to be the 500 greatest albums of all time.
I was inspired to do this for a few reasons. First of all, for many years I’ve wanted to do it. I was curious what I would learn from listening to lots of music which had been designated “Great” but in many cases I had never heard before.
I’d tried a few times in the past and, looking back, had always failed because of linearity. Start at number 500 and you have to work through a lot of material that might not be that great to get to the good stuff. Start and number 1 and you’re onto a path of diminishing returns.
Which brought me to my second (and possibly third) inspirations; if I could do this in random order it would add some unpredictability to the journey, and with my new found software programming skills (read: using Claude.AI to write code) I could create an app that would keep me on the path.
So back in May, with the help of this little app that I built, I started out on my musical quest: https://experiments.randomthebook.com/top500/
This morning I listened to the last of the 500. Here’s what I learned along the way…
You can’t expect to like everything.
I’ve got pretty broad musical tastes, but it still came as a surprise that I didn’t enjoy quite a lot of the music in the list. I don’t like Country and Western. I don’t like gangsta rap (a low point was when a rapper compared his penis to the Eiffel Tower). I don’t like much of Bob Dylan’s output.
It turns out I prefer The Beatles to the Stones.
I always thought it was the other way around.
Familiarity breeds love
I assessed each album on a very rudimentary scale: Love, Like, Indifferent, Dislike. Most the Loves were albums I knew very well before.
Compilations are cheating
I’m part of a small group that gathers once a month to listen collectively to an album and then share reflections. We take it in turns to bring an album to the group. There are only a few rules and one of them is “No Compilations”.
There are a few compilations I own that are great albums (Coldcut’s Journeys by DJ springs immediately to mind), but they are the exception that proves the rule.
There are a surprisingly large number of career-retrospective compilation albums in the Rolling Stone list, and they were mostly quite annoying. Especially the few complete career 7 disc box set ones.
Three tracks and you are out
Many years ago I realised that if I’m not enjoying a book after three chapters I should just stop. Maybe I’ll come back to it and enjoy it at a later data (Tomorrow and Tomorrow and Tomorrow, and Cloud Atlas both took me a few goes). Others, especially non-fiction books, I’ll probably have got the gist of by then anyway.
After a few albums in I adopted a similar rule. If I’m really not enjoying it after 3 tracks, stop.
There weren’t many albums this applied to, but there were a few.
I can quite happily listen to music in the background
Put a TV on and it will transfix my attention. But music can be quite happily burbling away in the background, I can hear it, but I can also get on with other things too. Not everyone is like that.
Ending on a bit of a high
The last album I listened to in the journey was Marvin Gaye’s amazing What’s Going On. That also happened to be the Number 1 album on the Rolling Stone list.
I obviously concluded that there was something wrong with the app and a bug meant that I’d ended on the “best” album of all (a fair shout on both counts).
But I’ve gone back, examined the code, tested the app, and concluded that I really did, totally randomly, finish on the number one album. And that then triggers all of the strange feelings of unlikely coincidence that have meant humans have had a strange relationship with statistical randomness and concepts of things like fate forever.
Which feels like a perfect way to finish the experiment.
The app is still running if you’d like to try it yourself…


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