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Can Letterman survive being the butt of his own joke?

Despite ratings spike for the Indiana-born funnyman, harassment concerns could dog Letterman's contract negotiations with CBS.

By Staff writer / October 3, 2009

David Letterman describes an extortion attempt over affairs with female staff members on his show, Thursday.

CBS/AP

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The joke about “creepy stuff” could have been directed at any number of recent liaisons by high-profile Americans like Mark Sanford or Larry Craig.

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But even when the trysts were his, Late Show host David Letterman, that paragon of geeky Midwestern cool, managed to elicit nervous laughter from the studio crowd Thursday as he explained an extortion attempt against him while admitting that, yes, he had had affairs with female staffers.

Letterman received plaudits for his honest admission as he helped unravel an alleged $2 million extortion attempt by a cash-strapped CBS news producer. But even though Letterman masterfully took hold of the narrative by coming clean about his role, as the Monitor’s Gloria Goodale wrote, the smoke has yet to clear from the sound stage.

Letterman’s admission comes as contract negotiations between Worldwide Pants, his production company, and CBS are set to begin for a 2012 extension. Revealing his workplace affairs could spark complaints of favoritism, especially since Letterman reportedly put one of his paramours through law school.

“… [U]nder sexual harassment law, there is a claim for harassment if somebody can come forward and say, ‘The boss was sleeping with other employees [and] they got favors and advantages that I didn’t get,’ “ CBS legal analyst Lisa Bloom said on the CBS Early Show Saturday

“Nobody has raised a claim, but there’s always that issue lingering out there,” she added. “So, this is why every company in the United States has a policy that an employer should not be having sexual relations with a subordinate, because it has the potential to create a hostile work environment.”

It’s far from clear how the legal battle and public reaction will play out. CBS news producer Robert “Joe” Halderman pleaded not guilty to the blackmail attempt on Friday in New York, and his lawyer hinted that there’s more to the story. At the very least, the discovery process in a criminal case could be eye brow-raising and potentially embarrassing for Letterman.