The Most Iconic (and Cringeworthy) Moments in Talk Show History

David Letterman admits to having affairs with colleagues

On October 1, 2009, the levity of David Letterman's usual program disappeared when the talk show host told viewers that he was the victim of an attempted blackmailing scam. Behind the scenes, someone had threatened to reveal a series of covert affairs with female coworkers unless Letterman doled out $2 million.

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Post originally appeared on Upbeat News.