Well, the Radio Rejects (shameless plug) may be the wave of the future when it comes to entertaining radio. The inmates are running the asylum, but hey, maybe we should just call it "grunge radio"...
Anyway, true story about pirate stations: when I worked in the Cayman Islands one of my many GMs had been a major player with Cox who burned out and semi-retired to the Caribbean (he's now back stateside working for a small group in Oklahoma). He told me that for a while he had a big-ass house in Tulsa and instead of hard wiring it, decided to put a Radio Shack FM xmtr in his attic. He programmed it to run off a computer and did a full imaging package. His tastes were somewhat odd...he was partial to trance ambience... but anyway where he put his xmtr apparently was high enough to cover quite an area. During one rating period someone in his neighborhood got a diary and put his bootleg "station" logo down. He said he was never so unhappy to see a station of his show up in a book! I guess all he could think of was the FCC kicking down his doors and the resulting headlines: "Radio Station exec Busted for Running Pirate Station film at 11!" complete with video of him being frog-marched out of his house into a cop car...