Remember Winamp? It's still good! It hasn't changed much in the past decade but why mess with a classic? Winamp revolves around the playlist and has many features and hotkeys to help you build a song mix with ease. Fire up Winamp, throw on some Nirvana and cutoffs and remember the 90s.
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Pro A huge selection of skins are available
Winamp allows skinning the interface and there are thousands of community created skins available.
Pro Functionality can be extended via plugins
A wide variety of DSP, input, and visualization plugins have been created by the community.
Pro Great search and Playlist functionality
Considerable functions to search and develop playlists.
Pro Good sound quality
The sound quality of Winamp is good, especially with DSP plugins like enhancer.
Pro RSS, Atom Podcasts, and Internet Radio streams (among other modern features) are available
Modern features are essential for power listeners nowadays, proving that Winamp (while an old app) still offers features users look for in a modern player.
Pro HTTP streaming support
HTTP streaming is necessary for both live and on-demand content, which it can deliver without lengthy buffering or waiting periods. It is also less susceptible to network hiccups than other forms of streaming.
The last stable release of Winamp was published on December 12th, 2013.
Con Relatively poor quality audio
Compared to other players, Winamp doesn't offer high quality audio.
Reason for Winamp's lesser audio quality compared to other modern audio players is that it uses deprecated audio output interfaces (APIs). In fact since Windows Vista onward, those APIs Winamp is using (such as DirectSound, WaveOut) are emulated in software mixer for compatibility purposes further distancing the audio path from the hardware.
Modern audio players support modern WASAPI audio output for direct access to the audio hardware (especially in WASAPI exclusive mode). For more info see Wikipedia's entry on DirectSound.