[mst]

We started using Winamp roughly at roughly the similar time, then... I think 1.91 was the first version I downloaded I even bought a license for it when it still was shareware, and I had some really nice custom skins for it, too

I had similar hearing habits, just like you. In fact, when I considered switching to the Mac in 2006 (when they switched to Intel CPUs), I spent quite some time looking for a Mac application that offered the same features as winamp: browse my Music folders and just play or queue whatever I double-click on. It took me a while to accept that there is nothing similar on the Mac and I might eventually have to have a closer look to iTunes (Winamp was running in VMWare at that time...). Once I did... well, see JoJu's post above, "12 years ago"

Not arguing in favor of any approach: both have their advantages. I like that I can search across my whole library when I'm looking for something and get instant results while typing already. However, there is music that I used to listen to quite often "back then", but because it didn't have proper tags, it got lost somewhere in the back of the library database and only get's rediscovered when I use search phrases that happen to be part of their file names.

I even subscribed to streaming services by now. They have disadvantages and I feel that listening habits can easily be "mainstreamed" by their suggestions and moderated playlists, however I also discovered lots of music on Spotify that I really enjoy and that would have never gotten my attention otherwise.