It can be hard to find a middle-aged celebrity who hasn’t been caught up in a scandal.
But in 2009, “Late Show” host David Letterman found himself in the eyes of one of the biggest scandals in the decade.
Letterman had been sleeping with multiple women who worked for him – all while dating , marrying and then fathering a child with his current wife, Regina Lasko.
One of those affairs was fairly serious. For years, Letterman had slept with Stephanie Birkitt — an intern who was eventually promoted to be Letterman’s personal assistant. But according to The New York Post, their affair ended after Letterman’s wife gave birth to a son in 2003.
Birkitt moved to date “48 Hours” producer Joe Halderman. But after their sudden breakup, Halderman was reportedly beside himself and decided to “shake down” Letterman for money in exchange for keeping Letterman’s affairs a secret.
Letterman found himself at a crossroads — either pay a disgruntled man an undisclosed amount of money with no real guarantee of privacy, or fess up himself.
And on one Thursday night in October 2009, Letterman delivered one of the most truth-bombing monologues in late-night television history:
However, his confident demeanor in the face of the scandal was not how Letterman genuinely felt.
The following weeks, Letterman continued to deliver hilarious monologues and interview celebrities, but in reality he was depressed.
In a new upcoming biography titled “Letterman: The Last Giant of Late Night,” New York Times reporter Jason Zinoman — who penned the book — detailed the brutal depression that actually followed the moment Letterman chose to get ahead of the scandal.
People reported that in the book, Letterman was reviewing the memorable monologue with writer Steve Young when he broke down a little, saying:
“I’m in hell. I will always be in hell until the day after, when I will go to hell.”
And after he exposed his situation to viewers around the world, Zinoman wrote that the talk show host was “shaken.” And despite laughing alongside the blindsided audience, Letterman described the experience as terrorizing:
“It was akin to having killed your family in a car crash. It was like that to me. I was afraid my family was gone.”
But Letterman’s wife, much to the host’s relief, decided to stay by his side.
In a 2015 interview with Rolling Stone, Letterman articulated his gratitude for his wife’s decision. He also said that he, himself, will eventually tell his son Harry:
“He will [know about it] one day. We’ll have to have a conversation about it. But not yet.”
However, one person he did have to discuss the “lowest point” in his life with was his beloved mother.
Letterman’s mother, Dorothy Mengering, garnered a place in American viewers’ hearts the very first time she appeared on her son’s show in the 1990s, when she was featured in a guest segment called “Guess Mom’s Pies,” according to the Associated Press.
Both her Hoosier accent and endearing motherly love for her son made her an instant late-night classic.
In fact, she even published a cookbook in 1996 called “Home Cookin’ with Dave’s Mom” that detailed the secret recipes behind her famous pies.
However, on Tuesday, Letterman’s publicist informed the AP that 95-year-old Dorothy Mengering had passed away.
Although Letterman may have been afraid that exposing his private life would cost him his family, it is clear that his family never left – which includes his adoring mother.