Used to use Shoutcast for an internet radio thing I did. While it wasn't the most intuitive thing to set up, once it was working it never broke. Interesting to see that someone has found value in both WinAmp and Shoutcast when there are so many other solution that make it much easier to listen and/or broadcast music.
I still use it. Mpd has a shoutcast server built in and I use that to stream audio to various computers from my homebrew mp3 collection administration. Very useful.