30 most shocking moments in late night history
By Jeremy Dick
26. David Letterman admits to having affairs with co-workers
Most fans of David Letterman during his heyday in the 90s and new millennium could always count on laughing and being entertained when watching his late night talk show, but on October 1, 2009, the show took a dark and unexpected turn. On the air, Letterman told viewers that he was the victim of an attempted blackmailing scam, with someone threatening to reveal his behind-the-scenes affairs with female co-workers unless Lettermain paid him $2 million.
Even more shocking, Letterman then confessed that he had, in fact, been having multiple affairs with several of the women he had worked with. Rather than complying with the blackmailer, Letterman took one step ahead of him and organized a sting operation with the police that resulted in the arrest of producer Joe Halderman on larceny charges.
Just to make sure Halderman couldn’t get revenge and divulge Letterman’s secrets, the beloved talk show host revealed these skeletons in his closet himself in front of millions of people watching. Nobody could encourage Letterman’s behavior, but the way he handled it by coming clean and taking down the man attempting to blackmail him was admirable, and his late night career was ultimately not affected as a result.
Next: 25. Conan whips out the dictionary