Well AOL bought it ... Milking something as long as possible instead of innovating is kind of their thing.
iTunes on Windows used to be really great if you just wanted music. It used to be that iTunes was considered a Trojan horse to show Windows users how good Mac software was.
Amazing how times change.
Yes I remember that the first time I used streaming music it was shoutcast.
It was really fantastic with hundreds of different music channels and podcasts. One radio station I was particularly fond off was called Atlantic sound factory. They had a goldmine on their hands and it's a shame they let it all go to waste.
I've been a di.fm subscriber for a looooooong time now. :)
I'm not so sure how successful that really would have been. There is a significant gap between Winamp falling out of favor and the rise of Spotify. The obvious winner in that gap wasn't any streaming service, it was Apple. The gap is basically defined as the period between when the iPod became ubiquitous and when the iPhone became ubiquitous. Granted, there is a few year period between when the iPhone was released and when streaming took over.
Spotify-like streaming services like Rhapsody existed during that gap but they weren't compatible with the iPod and even players they were compatible required a pretty cumbersome process in order to sync and listen offline. I think Rhapsody enjoyed a relatively brief period when smartphones became available and they could stream from there but it was a no-brainer to switch to Spotify once they launched in the U.S.
And then, at some points, the UX completely changed. It also started being spammy. Almost like the project was sold to some incompetent people. Then I felt like it lost its magic. It also happened to be the time when streaming from Napster became possible and I completely switched to it.. and then to grooveshark/deezer/all-the-others.
Winamp could have been Spotify but went in a completely different directions. Saying that may sound crazy, but that's what Netflix did. It was selling/renting dvd, saw streaming coming and did a full 180.