I remember playing with skins for a while, but since I mostly used Winamp without looking at it, I stopped caring about skins and appreciated the stock 2.x look. Who knew that a modular, black/gray aesthetic reminiscent of high end audio equipment would be timeless?
I've tried to use other players (Foobar, VLC) with Winamp skins, but they never looked or functioned right, so I kept coming back to the original.
Speaking of skeuomorphism, before MP3 was a thing and Winamp I played many a MIDI and wav file in addition to actual CD's on Audiostation: https://www.audiostation.org/
I'm using clementine from the first version. I kept using Amarok 1.4 after KDE reimagined it in 2.0, and Clementine keeps all the good stuff from the old Amarok.
In some cases, they're very skinnable and the ugly theme is just the default. Both Winamp and Foobar2000 were extremely popular in the desktop customization community when it was at its height around 2004-2006ish for that reason.
It's also because most of these projects don't have dedicated designers working on them. So you end up with the "designed by developers" aesthetic and let's be honest: we developers generally suck at designing UIs.
Does anyone know how the media library scanning was implemented in Winamp, I remember it was orders of magnitude faster than any (even modern) music players for very large music collections.
The first "useful" tool I ever wrote in the 90s (in VB 5 if I am not mistaken) was a M3U to HTML converter for MP3 playlists. Winamp added the feature a bit later.