As I think about it a little more -
The most hysterical thing I ever heard on the radio was in Houston on KQUE (102.9FM) in the late 70's or early 80's and wasn't meant to be funny. I think the DJ's name was Bob Jones and he was filling in on the 12A-6P overnight slot one weekend.
There are various versions as to why he was so messed up on this particular shift - A. he was drunk, B. on drugs (prescription or otherwise), C. sick with a stomach flu, D. all of the above
The Control Room was tiny and this was back in the day when stations had everything on carts (they looked like 8 track tapes). Anyway, there were 5 cart machines in the console and the problems began when he left 3 of the cart machines potted up and playing different songs simultaneously. It went downhill from there...
At some point he played, "I'd Really Love To See You Tonight" by England Dan and John Ford Cooley and after it finished he did a 5 minute dissertation of why he loved the song - after which he played it again - and again - and again.
After the third or 4th time - dead air - several minutes of dead air. Then you heard him answer the phone. His side of the conversation went out over 100,000 watts...
The climax of the night came around 4:30 or 5:00 AM: As he was giving the call letters - K-Q-U-E - he blew his cookies all over the console! Live and on the mic, for all to hear!!! More dead air, then the phone rings, and once again we hear his side of the conversation -- "Yeah, I know, I'm really sick, man... I just threw up all over the console. No, No, it's a mess - it's all over the board man. Yeah, I know, I gotta clean it up before my relief walk's in..."
Johnny Goyen, a DJ from another station was on his way home when he heard what was going on and ran tape on the entire night once he got home. That tape made the rounds for years in Houston, which is when I heard it about 1990. Needless to say, it would be Mr. Jones last air shift on KQUE.
That tape was the most side-splitting thing I ever heard...
CR Big Band