President Obama
Say you want to be the first sitting President to appear as a guest on a late-night talk show. You sure ain't gonna do Jimmy Kimmel. Leno's mainstream appeal — and the fact that he's not exactly known for asking tough questions — made The Tonight Show a perfect venue for Obama to explain the early stages of his economic plan to America. The March 19, 2009, interview was largely a chance for the President to hit his talking points, patiently explaining the AIG bailout and the struggles of Treasury Secretary Timothy Geithner. But during a lighter moment, the typically disciplined Obama stumbled, describing his awful bowling skills as "like the Special Olympics or something." Though Obama apologized for his choice of words, the remarks drew speedy condemnation from Tim Shriver, chairman of the Special Olympics board.