Love Life Leads To Extortion Attempt
In 2009, the newly married TV host shocked fans by revealing he had been the victim of an extortion attempt by someone threatening to reveal he’d had sex with female staff members. Even more shocking, he admitted was true! It later emerged that 48 Hours producer Robert Halderman allegedly had tried to blackmail Letterman because he believed the comedian was having an affair with his girlfriend, Stephanie Birkitt, who was also Letterman’s personal assistant. Halderman eventually pled guilty to attempted grand larceny.
During Letterman’s second 2009 on-air discussion about being the victim of an extortion attempt, he apologized to his wife, Regina Lasko, for being unfaithful. “She has been horribly hurt by my behavior,” he said, “and when something happens like that, if you hurt a person and it’s your responsibility, you try to fix it….Let me tell you, folks—I got my work cut out for me.” In 2013, Letterman sighed about mending fences with Lasko, 53, the mother of his son, Harry, now 10, “I’m still trying to fix it.”
DrewBarrymore Flashes Dave!
In the most salacious moment on his talk show, Drew Barrymore helped Letterman celebrate his birthday in 1995 by jumping up on his desk, gyrating around, and flashing her boobs. She then gave the surprised, pop-eyed host a kiss on the cheek.
Feud with Jay Leno
The comedians famously feuded for years after Letterman expected to be the successor to Johnny Carson on The Tonight Show—but Leno got the job instead. In 2012, Letterman couldn’t contain his delight when Conan O’Brien, who lost his own job on The Tonight Show after NBC brought Leno back, appeared on his Late Show to discuss the controversy. Letterman told O’Brien that Leno is “a bit of a brat.” Leno didn’t respond. The Tonight Show host stepped aside to be replaced by Jimmy Fallon this year. No word yet on who’ll replace Letterman.
Letterman’s 1994 Late Show interview with Madonna was totally out of control as she dropped the F bomb numerous times. In fact, it was the most censored episode in network TV talk-show history! During the bizarre appearance, Madonna also smoked a cigar and told the audience, “I gave him my underpants and he won’t smell them.”
After Letterman’s 2009 disclosure that he’d had sex with staff members, Holly Hester announced that she and Letterman had engaged in a year-long "secret" affair in the early 1990s while she was his intern and a student at New York University. She said the comedian called it off because of their age difference. A source also told the New York Daily News that Letterman kept a secret bachelor pad above his set in the Ed Sullivan Theater on Broadway where only his favorite young female underlings were allowed!
In 2005, police discovered a plot to kidnap Letterman and wife Lasko’s son, Harry, then one year old, and ransom him for $5 million. Kelly Frank, a handyman who had worked for Letterman, received a 10-year prison sentence as part of a plea-bargain deal in which prosecutors dropped the abduction charge -- and instead punished him for overcharging the Late Show host for work done at his Montana ranch. In 2007, Frank escaped from prison but was later recaptured by Montana cops.
Academy Award Debacle
Was Letterman the worst Oscar host ever? Many think the comedian’s March 27, 1995 hosting of the 67th Academy Awards was truly awkward instead of funny! In his most lambasted joke, Letterman introduced audience members Uma Thurman and Oprah Winfrey, saying, "Oprah...Uma. Uma...Oprah." But Letterman made fun of himself for the controversy later, saying on his talk show, "Looking back, I had no idea that thing was being televised."
MargaretMary Ray, a woman suffering from schizophrenia, began stalking the talk show host in 1998, believing they were romantically involved. She stole Letterman’s Porsche, camped out on his tennis court, and repeatedly broke into his house. Letterman told the New York Times that once he and a girlfriend looked up from bed and saw Ray staring at them from the hallway; she immediately ran away. Ray committed suicide in October 1998 by kneeling in front of a train.
Muse Or More?
Was Letterman’s longtime girlfriend, writer Merrill Markoe, the secret to his success? Markoe, who was his significant other from 1978-1988, was a writer in the early days of Late Night and created the popular segments “Stupid Pet Tricks,” “Stupid Human Tricks” and “Viewer Mail.” Sources said Markoe, now 65, also conceived many of the ideas behind the remote segments outside the studio. After splitting from Letterman and leaving the show, Markoe wrote about the relationship in her memoir Cool, Calm, and Contentious, giving him the pseudonym “Bobby.” After Letterman’s 2009 extortion and womanizing scandal broke, Markoe commented, “As you can imagine, this is a very emotional moment for me, because Dave promised me many times that I was the only woman he would ever cheat on.”