There's a prominent theory that President Trump decided to seek the highest office in the land out of pique at being roasted by former President Barack Obama and comedian Seth Meyers at the 2011 White House Correspondents' Dinner (reprised, in absentia, by Obama last spring). Trump denied that his stony-faced demeanor while Meyers and Obama mocked him meant he was angry, telling CNN last May that while the media said he "had a miserable time" and "felt humiliated" after the event, in fact, "I didn't feel humiliated, I had a great time. So the press is very dishonest." On Conan this week, comedian Jeff Ross backed the new president up.
"He doesn't seem like a guy who would handle a roast well," Conan O'Brien said. "It is odd, he loves being roasted — I've roasted him twice, actually — but he doesn't laugh," Ross said. "So you have to just keep going till you get him to break." Conan suggested this paradox might be because Trump loves being the center of attention, as in a roast, "but he doesn't want to laugh at himself," noting that Sen. Al Franken (D-Minn.) has observed that Trump doesn't laugh. "He'll smile, or he might, you know, sort of laugh at a situation, but he's not someone who would ever laugh at himself." Ross said he thinks Trump likes "the challenge of letting everyone know he that doesn't think it's funny, even though he wants to be roasted."
Ross said Trump really doesn't find his bankruptcies funny, however, recalling one of his jokes: "I read your book, The Art of the Deal — it had four Chapter 11s." Ross added he hopes he'll be rewarded for his roastmaster general services by being named Trump's secretary of offense. Jokes aside, Trump really doesn't seem to laugh much, he doesn't have a great track record at roasting others, and he's pretty sparing with his smiles. Peter Weber