Five (well, six) applications that bleed together radio/audio/new media (in alphabetical order):
iRate radio "is a collaborative filtering client/server mp3 player/downloader. The iRATE server has a large database of music. You rate the tracks and it uses your ratings and other people's to guess what you'll like. The tracks are downloaded from websites which allow free and legal downloads of their music". See also City of Sound on iRate, and an interview with the creator.
The Radio Program Recorder (RPR) is a portable AM/FM radio with a timer to record shows, and an FM transmitter to rebroadcast shows to your local radio. It also has a USB interface to transfer audio to your computer.
RadioSHARK is a Mac OS X-only FM/AM radio in hardware, that connects by USB. It includes software to record shows and pause live broadcasts.