Ronald Reagan (Phil Hartman)
Everyone from Robin Williams to Randy Quaid have played the Gipper on SNL, but once again, Hartman bested all competitors thanks to a classic 1986 sketch. Folks always joked about Reagan being an absent-minded president, one who believed he'd served in WWII because he'd once starred in a war movie. Hartman, however, plays him like an evil mastermind who, once the photo opps are over and reporters leave the room, starts barking orders and brokering deals with the Iraqis. It's a genius move of comedic counterprogramming: have that bumbling personality revealed as a giant ruse designed to fool the American public. Even his former administration wonks have expressed admiration.