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Live365 - 5,000+ online radio stations run by real people, not generated by computers.
MixTape - Home of MixTape, an OSX application for creating beat matched mixes with simple export to the web or iTunes.
Listen2MyRadio - Stop dreaming, start streaming. Free and premium Shoutcast and Icecast audio broadcasting.
Song Director - Song Director is a program that plays and keeps track of all your music files.
Wohooo.net - Create Your Own Online Radio Station
ServeStream - ServeStream is an open-source application that is intended for HTTP media player streaming, and the media server browser comes with the alluring support for custom online radio and Shoutcast streams.