WINAMP 5.3

Winamp has been around for a looong time and is still the one to beat as far as I'm concerned.  Hundreds of thousands of custom skins available to download means you can customize the look of the interface specifically to your tastes.

Foobar2000

Simple to use and supports just about every format on the planet.  With a highly customizable playlist display and keyboard shortcuts. And the cost is: $free!  Can't beat that.  Download it!+

Sonique (Win 95/98/2000/NT/ME/XP - exe - 2.66MB) - Cool looking software, but kinda clunky to use, not easy to figure out.  But hey, try it yourself, you might like it. 

Ultraplayer (Win 95/98/2000/NT/ME/XP - exe - 2.01MB) - Great looking little program with cool visualizations and great sound.  Very hip layout. Also supports video playback. My #2 pick next to Winamp. 

FreeMP3Player (Win 95/98/2000/ME/XP - exe - 2.45MB) - Nice little player that has great organizational tools included.  Automatically searches your hard drive for music files.

Quintessential Player (Win 98/2000/NT/ME/XP - exe - 2.48MB) - Very cool looking, great sounding player. Interface is very attractive and easy to use.  Great sound too!

CoolPlayer (Win 95/98/2000/NT/ME/XP - exe - 150KB) - Download this if you don't want a bunch of fancy features and interfaces clogging up your machine.  It just plays audio files, nothing more.  Sound is great.

C-4 MP3 Player (Win 95/98/2000/NT/ME/XP - exe - 1.12MB) - Cool looking LCD-like interface.  Easy to use, and the sound is sweet.

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