Like most ppl on this forum, I'm a huge Boston John fan.
It's worth mentioning that while he injects a lot of humorous, casual chatter on the frequency, his actual INSTRUCTIONS are phrased correctly (if memory serves).
There's usually a funny prefix on the callsign, or a funny comment at the end, but from what I recall, he doesn't jack with the instructions themselves, and I suspect that's why he has so few detractors.
Compare, "It's not rocket science, it's JET BLUE....232. Boston Tower, wind xxx at yy, rwy zz cleared to land" with, "Jet Blue 232, you're cleared to land, rwy xx"
The first is a typical Boston John line...funny prefix, spot on phraseology for the instruction. The second is a casually (and incorrectly phrased) landing clearance which I've heard on the air from time to time by other controllers.
The other talent he has is dialing back the gags when time is tight. Good stuff.