When comparing Winamp vs RadioTray, the Slant community recommends RadioTray for most people. In the question“What are the best music players for OSX ?” RadioTray is ranked 15th while Winamp is ranked 16th. The most important reason people chose RadioTray is:
Because it's designed to be extremely minimal, Radio Tray is extremely easy to use. The entire UI consists of a dropdown menu where you can hover over the genre you wish to listen to, and then you can choose a specific radio station to listen to.
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Pros
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 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 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.
Pro Super easy to use
Because it's designed to be extremely minimal, Radio Tray is extremely easy to use. The entire UI consists of a dropdown menu where you can hover over the genre you wish to listen to, and then you can choose a specific radio station to listen to.
Pro Plugins available
You can extend the utility of Radio Tray through plugins.
Cons
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.
Con No Major updates
There are no major updates since version 5.
Con Heavy
At the beginning it was simple to download and install, now it has so many things it became very heavy to download.
Con Cluttered interface
With all controls, skins, and options it's hard to find the basic commands.
Con Not usable for locally stored media
Radio Tray is intended to be a simple way to stream online music. As such, it doesn't work as a music play for locally stored music.
Con Possibly abandoned
The last release (0.7.3) was back in August 2012, and the last commit is listed as January 2015.