The campus radio thread made me think ...of my favorite 'songs about' radio. The most commonly mentioned is probably Harry Chapin's 'W.O.L.D.',and I've always dug George Jone's "Radio Lover",about a jock's cheating spouse,but this obscure little story song really grabs me. (Can-Con too, I believe) Take a listen,and add your contribution if you have one.
http://www.youtube.com/watch?v=AYQZMtLv9ng