The 'least cool' band I got into story has to be the Simon & Garfunkel one, though. I was a teenager at the time, on holiday in Newquay, UK, and I was sitting in some restaurant. They stayed playing a bunch of what I later found out were Simon & Garfunkel songs. I asked my dad if he knew who it was, he told me, but damn, I was getting condescension vibes there.

Anyway, bought their greatest hits album shortly after.
https://youtu.be/DdIC4ZXVq9k

In his defence, my dad was mostly a dick, but he did have good taste in music for the most part. It was through him that I got into Dire Straits and Pink Floyd. And I know he appreciated my taste in music 'cos the bugger stole a load of my CDs 😋

Last one, which is more recent and a little different. I was watching Luke Cage and there was a nightclub scene with (as I remember) an act doing a warmup, or audition or something. Loved the song and, thankfully this was recent so it was easy to look up online, turned out to be Jidenna - Long Live the Chief
https://youtu.be/H_AQFnqMY3E

Reason I say it's a little different is it feels like I came across it less 'organically', being introduced via a TV show. Granted, the Morcheeba and Simon & Garfunkel one were marketing exercises also, but in a different way - they were used to create a particular atmosphere/ambience, whereas the Jidenna/Luke Cage thing felt more like a product placement. Out of all those stories, that's the one where I only really ended up liking the one track rather than getting into the artist generally.

@ldroadie Skye, or Skye Edwards. She's done a bunch of solo stuff as well 🙂
https://en.m.wikipedia.org/wiki/Skye_Edwards

@66ALW99 Sorry this is late. I only recently discovered Morcheeba was the name of the group. Skye is the singer. D'oh. I have only rarely felt like this much of a dummy before. Rarely.