I had just graduated graduate school for international economics, and was working for a government contractor who only hired me because I had a masters (they could charge the government more). Because of this, I literally had nothing to do and would just sit in the office.
I eventually figured out an excuse to get my employer to buy Photoshop for me and I started learning it on company time. When Winamp came out with the update to add skins, I ended up making one of the very first skins (meshAMP) which became really popularly.
https://archive.org/details/winampskins_meshAmp
(I am cringing looking at it now)
This led to contract job with STB (to design interfaces for a TV Tuner card they had) and eventually 3DFX (paid in 3d video cards), and eventually a career change and a job as a graphic designer.
Except, I was not a good designer, so I quickly learned to program (ASP.net and then JAVA), which led to Macromedia Flash, which led to Macromedia Generator, which eventually led to a job offer from Macromedia (now Adobe), where I still am (sadly, sans Flash).
Anyways, thank your WinAMP!
Anyway your winamp skin is cool
Skinning was pretty easy to do. The packaging format was a zip archive with a renamed extension. You could do a lot with a little photoshop skills and trial and error.
So many people used it that skins would get a lot of distribution, too.