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These Anchor Fails Are So Embarrassing You’ll Feel Secondhand Shame

David Letterman’s Shocking On-Air Confession

David Letterman is usually in high spirits during his show, but during an episode of his late-night program on October 1, 2009, the host stunned viewers by revealing he was the target of a $2-million extortion attempt.

The blackmailer, identified as CBS producer Joe Halderman, threatened to expose David’s intimate relationships with several female staff members. In response, the host cooperated with authorities in a sting operation, leading to the exec’s arrest. The audience reacted with a mix of laughter and disbelief, uncertain if the comedian was joking. This candid admission shed light on the complexities behind the scenes of late-night television.

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