Winamp
It frightens me more than a little that AOL still rules the media player roost. After flubbing the launch of the Winamp 3.x series, they redeemed themselves with Winamp 5 a short time later, completely bypassing a v.4 release. Winamp 5 just got a slight facelift and a healthy dose of new features to go with the improved appearance. As with previous versions, Winamp supports audio and video playback. This update includes support for AOL radio, including XM channels. Possibly the biggest boost to the player, from my perspective, is the inclusion of a podcasting directory, offering the first viable alternative to iTunes for an all encompassing media player/podcasting experience. One quirk about subscribing in Winamp is the podcast feature is set to never update by default, so subscribed podcasts aren't downloaded. Predixis MusicMagic playlists are another cool update, offering playlists built through a computer analysis of your music collection (also available as a free plugin for other players). SHOUTcast Radio and TV integration are par for the course considering they are both a part of the Nullsoft family. For a $20 upgrade you get ripping and encoding of WMA, MP3 and AAC files, which likely isn't worth $20 since there are several free solutions capable of doing all three (iTunes and Windows Media Player being the two obvious alternatives). All in all the new features in the free version make this a worthy upgrade to a product with a great history and as much as I hate AOL in general, I'd hate to see Winamp go away due to lack of support from the community. [Windows 9x/2k/XP $0.00]