You are romanticizing Winamp 2. It did many things, and not all well. It played a lot of audio formats besides MP3 as well as video formats. It was a damn SHOUTcast server. It had a frustrating playlist manager. It was skinnable. It had a hardware-accelerated, extensible visualizer. It had a damn RSS aggregator and website scraper for automatically downloading songs. And let’s not forget that it had support for syncing to many portable audio players, including the iPod. It was every bit as full-featured (or bloated) as iTunes.
> And let’s not forget that it had support for syncing to many portable audio players, including the iPod.
I'm pretty sure you're thinking about Winamp 3 or 5. Winamp 2, upon release (in 1998!) had no such feature IIRC. It didn't even have a "Library view" of all your MP3s, it only had a very rudimentary playlist.
The main thing about Winamp 2 was that it was fast. For example, the skins were just bitmaps (none of the crazy theming that Winamp3 enabled). The visualizations were delivered by a set of plugins -- all of which you could get rid of.
It's much more enjoyable to use, though. Perhaps it's the dark theme, or the analog-looking EQ but when I listen to music from iTunes, it just feels like I'm launching songs from an MS Office application or something.
I also believe that WinAmp just sounds better. Even after playing with the EQ on iTunes, I can't get it to sound as good as WinAmp.
I really dislike iTunes, but I find this claim hard to believe. In the audiophile community, we usually test such claims with double blind tests. Interestingly enough, a metal wire coat hanger held up just as well against $100 premium Monster audio cables.