The Darkest Conan Joke So Far on the Tonight Show, Video. As a HUGE Conan O’Brien fan, I have been waiting for him to break off a classic 1 P.M. joke about 2 hours too early. Monday night was not disappointment. This joke is not BAD, but it is definitely a departure from Jay Leno’s very tired/ very safe garbage. BTW Jay Leno’s very tired very safe garbage will have new shows this fall.