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MP3 Players

I suspect this section will grow considerably over time.

Winamp 
Winamp is the venerable player, still used by many, but it is suffering from bloat.  It has many convenient features, it is reliable, it converts MP3 to .wav, etc., but it has also added useless features and uses more CPU horsepower than some other players.One very cool addition that folks are raving about is MAD (MPEG Audio Decoder).  It is a free Winamp plug-in located at http://www.mars.org/home/rob/proj/mpeg/mad-plugin/.  Many folks are very impressed with its sound quality.
CoolPlayer 
CoolPlayer is freeware.  It is cool.  It is not as CPU-intensive as Winamp.  It can also convert MP3s to .wav.  It is becoming popular for very good reason.
Sonique 
Sonique is held in very high regard by many who consider its sound quality to be far superior to Winamp and other players.  It can really eat up some CPU time.  You need to be the judge (well, actually The Judge needs to be The Judge, you just need to be your own judge).
MusicMatch Jukebox
Not held in very high esteem by regulars for a long time, MusicMatch has upgraded its encoder from Xing to a Fraunhofer CODEC lately.  YMMV (Your Mileage May Vary).  It is difficult for a single program to do everything well (play MP3s, CDs, encode, make playlists,  etc.)  MMJB has lots of features, has good marketing and gets good reviews from MP3.com and mainstream publications.
Windows Media Player
Media Player plays lots of stuff and does OK.  Watch out.  It is very intrusive and will take over your entire machine and want to play every media file type.