There is no question to how superior winamp is. It only has the things you need unless you download winamp pro where as wmp has all this random play list creation ---- nobody understands or uses. Plus wmp is made by microsoft making it even more ---- and its also memory hungry and looks gay. You will also notice you can get a winamp sig, but you cant get a wmp sig, in Diablo II you can get a winamp profile but you cant get a wmp profile. wmp is stupid, ---- and over rated. Get winamp now!
Not only does winamp look better with custom skins, than WMP, I got the PRO version, and I am 100% happy. You can even connect to Porn on it It's Half-Assed, but its good effort from Nullsoft. It kicks the ---- out of WMP. Afterall Winamp, it really kicks the llama's ass. (No not you llamaman hehehe)
I prefer to use Musicmatch Jukebox. You can access all your music in a library, creat playlists, then upload you playlists to your MP3 player. And you can get a free version, whihc is still very good.
I use to use winamp but now use wmp. I have the kenwood skin so it's compact and sleek looking. Never had a problem with either just I'd rather keep the program that came with windows over one that's not. That is if they r equal in quality.