We have been using Musicmatch to play entrance music for the wrestlers, but it's a bit ungainly and doesn't allow for mouse-click fadeout.
Any suggestions for a better program, maybe one with on-screen hotkeys?
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I use Winamp 2.7 (or 2.8, I forget; wrong machine at the moment) for a lot of music because I can just click in Windows Explorer and Winamp fires the song right away, and there's crossfade playback so when you click on a second song it fades the first and then fires the second. I used it for a webradio show I did briefly (not for music, but for elements) and it worked well. I don't know about fading out just one song and not starting another, though.
Later versions of Winamp took out the crossfade for whatever reason, or at least the versions up to 3.x when I stopped checking.
You might Google for free radio automation software. There's a few out there you can use at no charge without piracy concerns, though they're usually rudimentary. It might work for what you need since most programs have a cart fade option for each element, but you'd probably have to load your songs out of a library (though this would only take a second or two) rather than hotkeying it.