To be fair I haven't used Winamp in years, since I started using Spotify, thing is with the userbase winamp had/has they could of done similar things to Spotify and it could of been a goldmine for someone, AOL though, how the hell are they still in business...
I know that Winamp was popular in its day, but I really don't know what was so good about it. What made it stand out above the others? All I can remember of it was an endless amount of skins.
Just be a nutter... life becomes much more exciting, and people won't expect anything more of you...