3. Letterman Admits to Sex Scandal (October 1, 2009)
Sometimes when Letterman has to speak candidly to his audience, he finds just the right balance between seriousness and humor. But in 2009 when he discussed with the world a blackmail plot involving secret sexual relationships he'd had with female staff members, he initially stumbled with the tone. "I have a story to tell," he said from his desk. "Would you like to hear a story?" The audience cheered, figuring they were going to be treated to an amusing tale. Only slowly did it become apparent that the details of Dave's story weren't funny: a package of incriminating material, a demand for $2 million, a threat to expose all of Letterman's past sins. As the crowd's laughter grew increasingly more awkward, the host finally admitted his infidelity. The whole incident shown light on the private life of a man who prefers keeping all of that out of sight. "I think [CBS] would have had good reason to fire me," Letterman told the New York Times last week about his sex scandal. "But at the time, I was largely ignorant as to what, really, I had done."