I rather liked Winamp until I moved to Windows 7.
Dunno why, but it stutters like a bitch when it isn't the foreground application (nothing else gives me this issue) which is a big problem when I'm trying to listen to stuff in the background.
So I let VLC handle that job now; it works great though it does eat up a bit more RAM (which I have in no short supply now, at least).
Winamp can stay dead for all I care, I've had a lot of bad experience with it (instability and such, with each new version being worse than the one preceding it). Granted, it's been ten years since I last used it so it may have gotten better. But ever since I discovered JetAudio I've never had a reason to look back.
What version was that? Alpha 0.1? Because Winamp has never crashed for me. Even when you where able to run two of them at once.
Or rather what type of broken PC did you have when you used it? It just got better with the patches as it added more support for different sound files.
It was somewhere around version 3, on a Pentium 4. It was bloated, slow, and it had the tendency to consume way too much resources. As I said, it's likely the devs fixed the following verions but I never had a reason to look into them.
I checked out Foobar! And I went back to Winamp. I don't get the "bloatware" complaints either and I'm happy enough with Winamp's mod and codec support. But what really does it for me is the super-quick and painless way it handles folders: I don't bother with playlists or anything, I prefer to just select from a list of directories and play. Winamp is perfect for that, Foobar most definitely is not - nor is anything else I've run into in the many, many times I've investigated other players. It's admittedly a pretty specific feature, but for me it's a deal-breaker.
Also: BEST. MEDIA PLAYER. EVAR.
AOL still exists?!
This is the point that surprises me more than the actual subject.
I used Winamp for a while in high school, then switched to iTunes. Then switched to something else, I don't recall what. I've had bad experiences with audio programs just not working for me. That and I just don't personally own enough music to make any of them worth a time investment.
One thing I always liked about Winamp is that it switches to the next song instantaneously. Not like VLC were there a .2 second pause. Helpful for those albums that are just one recording session split up into different songs.