Don’t Expect Top Ten Extortion Plots on Letterman

After ‘Late Show’ sex shocker, writers likely not to use case as fodder.

Last Updated: October 2, 2009 @ 8:38 AM

David Letterman’s shocking on-air admission that he had sex with female staffers and that he was the target of a $2 million extortion plot – dark as it is – was revealed in a light-hearted, self-deprecating tale from his desk.

“The creepy stuff was that I have had sex with women who work for me on this show," Letterman said on Thursday’s show. "Now, my response to that is, ‘Yes I have.’"

"And would it be embarrassing if it were made public? Perhaps it would, perhaps it would – especially for the women.”

[Audience laughter.]

Classic Letterman.

But unlike other creepy personal sagas that have peppered the “Late Show” host’s past, don’t expect Dave to use this one as future joke fodder.

“I don’t plan to say much more on this particular topic,” Letterman said on Thursday’s show.

A source at CBS said he expected Letterman and his writers to adhere to that plan.

This, despite Thursday’s studio audience finding dark humor in Letterman’s delivery.

"This whole thing has been quite scary. I had to tell them how I was disturbed by this. I was scared for my family. I felt menaced by this man. I had to tell them all the creepy things I had done."

[More audience laughter.]

"Now, why is that funny?"

Letterman, whose production company is called Worldwide Pants, is no stranger to creepy characters (and I don’t mean Alan Kalter).

In the ’80s, the funnyman — who’s made a career out of poking fun at others’ sexual peccadilloes, particularly Bill Clinton (and Sarah Palin’s daughter, a joke for which he was criticized for and later apologized) — had a stalker, Margaret Ray, who, among other things, stole his Porsche and trespassed on his New Canaan, Connecticut property, and was eventually arrested in Indiana near where Letterman’s mom, Dorothy, lives. Ray committed suicide in 1998 in Colorado.

Until then, though, the stalker jokes appeared somewhat regularly, though not nightly. In 1990, Letterman’s head writer told People that Dave is "fatigued by his own caution.”

In 1993, on Letterman’s last NBC show, his “Top Ten Things I Have to Do Before I Leave NBC” included number two: ”Send change-of-address forms to that woman who breaks into my house.”

In 2005, a handyman, Kelly Allen Frank, was arrested and sentenced to 10 years in prison for his plot to kidnap Letterman’s young son, Harry, and a caretaker, in another planned extortion attempt.

Perhaps the most bizarre, though, was Colleen Nestler, a Santa Fe, New Mexico woman who told a judge that Letterman was torturing her through “code words such as ‘Marry me, Oprah’” uttered on his show. According to the Daily News, the judge “bought Nestler’s complaint and granted her request to order Letterman to stay 9 feet away from her and ‘no longer think of her.’” That ruling was eventually tossed out on the account of it being, uh, insane.

The whole thing is going to help Letterman’s ratings. Last week the “Late Show” drew more viewers than the “Tonight Show” for the first time since 2005.

But those tuning in tonight to see if Letterman will reference the sex/extortion plot will likely be disappointed – Letterman pre-tapes his Friday shows, usually on Mondays.