50 Mortifying, Awkward, Yet Incredibly Entertaining Moments You’ll Ever See In Talk Show History

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Letterman Admits to Having Affairs

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When you’re the host of a popular talk show, it’s tough to not be forthcoming with your audience about your bad behavior. So by 2009, Letterman could no longer keep it secret that he was the victim of blackmail after someone threatened to reveal his affairs with tons of female colleagues over the years. Although Letterman paid around $2 million to shut the person up, he eventually admitted to his faults while finally involving the police so that they could catch his blackmailer. Although it wasn’t the best for his career, it wasn’t a death sentence for the talk show host either.