I posted to my Facebook asking "does anyone still use this thing?" and a whole pile of people enthusiastically responded that they're still on Winamp 20 years later. Amazing the goodwill software can generate just by not sucking ...
Winamp radically not sucked by being basically the only piece of software in that space that didn't try to turn your computer and your love of music against you while you were using it. It doubled down on that pile of win by being highly competent at what it set out to do as well. That rightfully earned much love.
A lesson a great many web service companies could learn from today.
That said, Real's open-source version, Helix Media Player, was not awful (and didn't have the same tentacular behaviour).
Picky point: Apple opened the iTunes Music Store on April 28, 2003. The iPod came first.