Letterman Brings Sex and Extortion to Late Night

Updated: Oct. 2, 2009 at 11:40 a.m.

Confessions have become something of a staple for guests on late-night comedy shows. Stars as varied as Hugh Grant, Michael Richards and Kanye West have made appearances to talk about — and publicly apologize for — their mistakes. But the guy twisting in the spotlight on last night's Late Show with David Letterman was Letterman himself.

In between his opening monologue and his nightly Top 10 list, the 62-year-old comedian told his studio audience he wanted to tell them a "little story." He then went on to describe a three-week ordeal in which a man had attempted to blackmail him to the tune of $2 million for sleeping with female members of his staff. (See the top 10 disastrous Letterman interviews.)

Sometimes humorous, sometimes serious and occasionally showing flashes of nerves, Letterman explained — to awkward clapping and giggles — that having received a threatening package in the back of his car early one morning, he and his lawyer had called in the Manhattan district attorney's office.

The DA's office ascertained that the alleged blackmailer was serious, then arranged to have a fake check cut, handed it over and then arrested its recipient, whom CBS has identified as one of its employees, Robert "Joe" Halderman, 51, an Emmy-winning producer who had worked on 48 Hours.

Reportedly, Halderman lived until recently with Stephanie Birkitt, Letterman's personal assistant and a sometime character on his show. In 2002 she told Entertainment Weekly "He's the best boss I've ever had." Extracts from her diaries were reportedly in the package in Letterman's car.

As a blackmailing scheme, it was almost comically bad: the alleged extortionist threatened to write a screenplay about Letterman's affairs. "He's going to take all of the terrible stuff he knows about my life — and there seems to be quite a lot of terrible stuff he knows about — and he's going to put it in a movie," explained Letterman on the show. Still, the host was clearly unnerved. "I want to reiterate how terrifying this is," he said. "I am a seething mass of Lutheran Midwestern guilt." (See the top 10 late night jokes.)

Apparently neither the extortion attempt, nor the fact that Letterman slept with women on his show, were news to Letterman's wife of seven months, Regina Lasko, who had told Letterman's mother Dorothy Mengering about it earlier in the day. "I'm looking forward to seeing the show to see what he has to say," Mengering told the New York Daily News. "I really just found out today."

Lasko and Letterman have a 5-year-old son, Harry, and have been dating since 1986. The comedian now wants to put the "bizarre experience" behind him. "I need to protect my family, I need to protect myself. I hope to protect my job," he said in one of his serious moments, before making a joke about how nobody in the grand jury believed he had had sex. (See the top 10 political sex scandals.)

While Letterman seems to be in no immediate risk of losing either his family or his job (ratings from last night's telecast will likely be stratospheric), his troubles may not be over. Having sex with people who were his employees or whom he managed could leave him, or CBS, open to a sexual-harassment lawsuit. It's certain the comedian has given the network's lawyers plenty of reasons to be up at night.

Letterman has also probably given truckloads of material to other comedians — or even his own writers. Let's just say he may come to regret calling his company Worldwide Pants.

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