In 2001, when I first began listening to Internet radio, then-Clear Channel had several of its stations streaming through broadcast.com. That summer, those streams were stopped due to a requirement by ad agencies that advertisements using union voices not be streamed. Clear Channel began restreaming its stations that fall (in November if my memory is correct) with new ad insertion technology put into place so that the union-voiced commercials wouldn't play on the streams.
Clear Channel didn't, however, use broadcast.com for any of its streams again. It used a new platform that eventually became iheart.com. Again, going by memory, the first Clear Channel station to return to webcasting was Cleveland's WMJI-FM, and I listened to the stream for a bit after reading about it in Kurt Hanson's "Radio and Internet" newsletter.