Winamp 2 was the music player of choice of discretionary users who knew to seek out software on their own. Winamp 3 came out and it was so colossally awful that

Winamp 2 was the music player of choice of discretionary users who knew to seek out software on their own. Winamp 3 came out and it was so colossally awful that most people stayed on 2. If you bought your computer in a store -- like most people in the US at the time -- instead of building your own, it came bundled with some other product: WMP at least, possibly MusicMatch, RealJukebox (eventually merged back into RealPlayer), which you were likely using. Getting your Nomad or iRiver, a comparable devices to the iPod, to work with that, was not as smooth as the iTunes-iPod combo.