David Letterman’s Taste in Women

Before Jay Leno and Conan O’Brien went to war, late-night television had another scandal on its hands: David Letterman’s affair with a young female staffer and the alleged extortion plot by that staffer’s boyfriend. In a new piece for Vanity Fair, Mark Seal calls Letterman “one of the most unhappy, insecure, guilt-ridden, self-loathing, self-pitying people on the planet.” Over the years, he rejected advances from celebrities like Drew Barrymore, Madonna, Ellen Barkin, and Julia Roberts in favor of plainer, and sharply intelligent women. His staffers, for their parts, worship him. “It’s like a cult,” says a former insider. “You arrive as an intern and stay for life, and people do fall in love with Dave and behave in a way that might not be considered appropriate in a professional working environment. People really feed on wanting positive reinforcement from him. It was intoxicating to me, and I can see how someone could cross the line. It’s like Jesus Christ saying, ‘Hey, let’s go to dinner!’ You’re going to go, ‘Wow! He chose me!’ If he’d hit on me, I probably would have accepted.”