Conan O’Brien takes over The Tonight Show from Jay Leno in June, but will middle America take to Conan? Not least of all the obstacles to his success will be Leno himself, who will now start a 10 pm show. Author Lynn Hirschberg notes, “O’Brien (like his time-slot adversary, Letterman) does not have Leno’s cozy relationship to the Middle American viewer.” And Conan himself admits to being unhappy at first with the situation. “It took me about 45 minutes of, ‘Really?’ I think, realistically, that Jay will be doing the same show he’s doing now,” he says. “I knew that there was this thing that was starting to brew that poor Jay was being pushed out by Conan. Jay was clearly becoming unhappy, and it had the makings of a situation that would make me unhappy. … “What I realized is, I’m still doing The Tonight Show. That was my dream. When I can’t sleep and it’s 3 in the morning, I’m not thinking about Jay. I’m thinking about all the things I want to do on the show.”