Off the top of my head among both living and dead:
Jennifer Lawrence,
Frank Zappa,
Joan Rivers,
Sarah Silverman,
Jimi Hendrix,
Marilyn Manson,
Salvador Dali,
& Gilbert Gottfried.
I concur with some of the others mentioned in the thread especially Robin Williams.
Challenge accepted. Good thing you didn’t have money riding on it.
The best interview on a talk show I ever remember seeing was a Tonight Show when Johnny brought out Jim Henson for an interview promoting Henson’s first prime time broadcast network special. This was the special where Henson introduced Dr Teeth and the Electric Mayhem to the world. Anyway, Henson brought Kermit out with him. Johnny greeted them both, had a brief conversation with Jim, and then, being the sport that he was, started interviewing Kermit who was pissed off.
That’s just a short clip. As the interview went on, Kermit would get more and more pissed off and Johnny would try to calm him, and then Carson would stop and say “Wait! I’m arguing with a piece of green felt!” and resume talking to Henson. And then Kermit would say something and Johnny would start talking to Kermit again. Henson pulled the trick on Carson maybe 3 times.
I’ve seen Patrick Duffy on the Johnny Carson show a few times, and he is funny. He always makes me laugh out loud.