Winamp for me too. My PC is not great, yet I have a playlist of over 1000 (perfectly legal...) MP3's and I dont get a single complaint from Winamp. It even throws in some nice visual effects and a fades in and out on each track!
On the other hand you have Window$ Media Player. It spends half its processing power trying to sneakily connect to the internet to get information it doesnt really need, and tell some server what you are listening to if previous Micro$oft softwares are anything to go by.
Also plugins. How cool can they be ^_^
Especially its combined functionality with Trillian. People who use Winamp over WMP are the people who will use Trillian over MSN M. Therefore you get lots of intergrational plugins for much coolness. "Currently listening to: xxxxx- xxxxxxxxx" in my name. Cool huh?! None of that for WMP, oh no!
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