Audacious Facts About David Letterman, The Rebel Of Late Night

April 13, 2023 | Danny Bianco

Audacious Facts About David Letterman, The Rebel Of Late Night

There was truly nobody like David Letterman. The longest reigning late-night host in history, Letterman was quick-witted, irreverent, and hilarious. But it wasn't all laughs—for David Letterman, fame came at a terrible price. So what was Dave's life like behind the curtain? Why did Oprah hate him for so long? What made him walk off the set in the middle of a live taping? Dive in and learn more about the rebel of late-night.

1. He's From Indiana

David Letterman was born in Indianapolis in 1947 to Harry and Dorothy Letterman. Fans will know Dorothy as "Dave's Mom" from many appearances on his show, but his father will be less familiar. Young Dave adored his dad for his sense of humor, but sadly, Harry never saw his son become a comedy icon.

david letterman

2. He Almost Lost His Father As A Boy

The Letterman family endured a horrible scare when Dave's dad Harry suffered a sudden heart attack at just 36 years old. He survived, but this brush with death hit the youthful Dave hard. He developed a crippling fear of his father's mortality. This stuck with him even as he grew into a young man. But that wouldn't stop him from making his mark.

David Letterman factsGetty Images

3. His First Gig Fired Him

How does a midwestern boy from Indianapolis end up hosting a late-night show for decades? He starts at the bottom of the ladder and works his way up. Letterman's first show business gig came as a talk show host for a local radio station. It didn't last long, though—the station soon fired Dave for his "irreverent treatment of classical music." Apparently, classical music fans can't take a joke.

But one little firing wasn't about to keep David Letterman down...

David Letterman factsGetty Images

4. He Was A Weatherman

While Letterman had scandalized Hoosiers everywhere with his edgy classical music comedy, he must have impressed someone while working in radio. Fresh off his firing, Letterman landed a job at a local TV station as a weatherman. Finally, David Letterman stepped in front of a camera and into people's homes—and instantly, audiences could tell something was...different about him.

David Letterman factsClover Power, WTHR

5. His Weather Forecasts Were...Unique

It's hard to imagine David Letterman as a local TV weatherman—and to his credit, he was nothing like any weatherman you've ever seen. This gap-toothed 20-something soon became notorious for his bizarre weather reports. He'd predict hailstones "the size of canned hams." He'd report the weather for cities that don't exist (apparently Bingree is expecting a lot of snow).

David Letterman was no ordinary weatherman—but sometimes his jokes went a bit too far.

David Letterman factsLate Show with David Letterman, CBS

6. People Didn't Get His Jokes

Nobody in Indianapolis knew what to make of this strange weatherman spouting nonsense on their TV screens. Letterman would often just riff off of whatever was happening, and people didn't always get the joke. Take the day when Letterman saw that his weather map lacked the border between Indiana and Ohio. Letterman joked that thanks to some "dirty political dealings," Indiana and Ohio were now a single state.

Letterman's bizarre and irreverent broadcasts baffled audiences, but one thing was certain—he was never boring. He had talent, but the Midwest was not the place for him. He just needed someone to push him to take the next step.

David Letterman factsClover Power, WTHR

7. He Married Young

Letterman married for the first time while still living in Indianapolis. He and his college sweetheart, Michelle Cook, wed in 1968. But, if anyone knows anything about Letterman's love life, it was only a matter of time before it went up in flames.

Jay Leno factsLate Night with David Letterman (1982–1993), NBC

8. He Got Off To A Rocky Start

In 1971, David Letterman finally appeared on national TV for the first Chris Economaki. While covering the Indy 500, the anchors confused him with another reporter. Not the best start, but don't worry: America would know who David Letterman was soon enough. His career was about to enter a huge upswing—but not before tragedy almost derailed everything.

David Letterman factsGetty Images

9. His Worst Fear Came True

Letterman spent his youth terrified of his father's mortality, and sadly, his worst fears came true in 1973. Just as his career was starting to take off, Harry Letterman suffered another heart attack, and this one was fatal. He passed at just 57 years old.

John Mulaney FactsGetty Images

10. His Wife Convinced Him To Pursue Comedy

Anyone who saw David Letterman's surreal weather broadcasts could see that this man wasn't meant for local TV. One such person was Letterman's then-wife Michelle Cook. Cook convinced Letterman they had to head west if he was going to get into comedy. Together, the pair of them packed up everything they owned into a pickup truck and set their sights on LA.

The trip would change Letterman's life forever. It was the start of his rise to fame—but it also spelled doom for his relationship.

Madonna FactsLate Night with David Letterman, NBC

11. He Was A Jack Of All Trades

So, David Letterman hopped in a pickup truck, drove to LA, and hit it big immediately, right? People fell in love with the weirdo midwestern weatherman, right? Of course not. Dave had to work his way up the Hollywood ladder, and that meant working on more shows than you could shake a stick at. From The Starland Vocal Band Show to Mork & Mindy, Letterman showed up pretty much everywhere.

But he was still a nobody. He needed someone to give him a leg up, and that's just what he got—from one of the most famous people on the planet.

David Letterman factsMork & Mindy, Paramount Television

12. Carson Noticed Him

In the 1970s, no one was bigger than Johnny Carson, and The Tonight Show was the ultimate destination for any up-and-coming young comedian. With so many random TV appearances, it was only a matter of time before the show's scouts discovered Letterman. Obviously, it was a huge deal—but I doubt even Dave himself knew what it would lead to.

Zsa Zsa Gabor factsGetty Images

13. He Was A Tonight Show Regular

If Carson liked you, it could open all kinds of doors in the comedy industry—and Johnny loved Letterman. Dave became a regular, and even landed the coveted guest-host gig on several occasions. Clearly, Letterman had a flair for late-night, so I bet you can guess what happened next...

David Letterman factsGetty Images

14. He Got His Start In The Mornings

David Letterman, the late-night legend, finally got his own show in 1980...and it aired first thing in the morning. If you think that bright and early is the wrong time for Letterman's acerbic sense of humor, you'd be right. Though critics loved The David Letterman Show, audiences couldn't be bothered to get out of bed for it. It lasted just four months before NBC canned it—and no one ever saw David Letterman again...

David Letterman factsShutterstock

15. He Finally Got His Big Break

Of course NBC was going to give Letterman another shot. Carson loved him, and a morning-slot might as well be a death sentence for any fledgling comedian. Two years later, Letterman got his second chance with Late Night with David Letterman. Not only was this show actually at night, but it aired in the coveted post-Tonight Show time slot.

Finally, Letterman had an audience primed and ready for him, and Late Night quickly became a beloved staple. But while his career was finally really popping, his personal life was in total turmoil.

David Letterman factsLate Show with David Letterman, CBS

16. His Marriage Fell Apart

Though Letterman's first wife Michelle encouraged him to head to Hollywood, she'd end up eating those words. Turns out, making a living as a comedian in LA is a little different than working as a weatherman in Indianapolis. Their marriage slowly fell apart at the seams, and the pair of them finally divorced in 1977. The first chapter in Letterman's love-life had crashed and burned, but within a year, an even more tumultuous one began.

Janet Leigh factsShutterstock

17. Then He Started An Even More Troubled Relationship

A year after divorcing his first wife, Letterman began a relationship with fellow-comedian Merrill Markoe. Markoe was a brilliant joke writer, and she spent years as the head writer and producer on Late Night. Many critics credit Markoe as the driving force behind the show's surreal humor. But unfortunately, Letterman and Markoe worked better professionally than personally. If Letterman's first divorce was rough, this split was even worse.

David Letterman facts Wikimedia Commons

18. He Cheated On His Girlfriend With His Future-Wife

Letterman doesn't exactly have the best record when it comes to fidelity, and it started while he was with Markoe. The pair eventually broke up for good in 1988—a full two years after Letterman started a relationship with his current wife, Regina Lasko.

David Letterman factsGetty Images

19. Not Everyone Liked Him

While Letterman's life behind-the-scenes was a total mess, at least his career had finally taken off. Late Night with David Letterman quickly became a huge hit. Young fans loved Letterman's bizarre, sarcastic, and often outright unpleasant persona. But while audiences were having the time of their lives, Letterman's style quickly started making him some powerful enemies.

David Letterman factsWikimedia Commons, Chairman of the Joint Chiefs of Staff

20. He Made Famous Enemies

David Letterman was basically the anti-Jimmy Fallon. He loved to mess with his guests and often gave them nothing but outright scorn. As you can imagine, certain self-important celebs weren't exactly used to this kind of treatment. Letterman frequently found himself getting into arguments with his guests live on air. This led to now-legendarily awkward interviews with the likes of Madonna, Shirley MacLaine, and Cher, who flat out called Letterman an ***hole on his own show.

Yup, Letterman loved to mess with his guests—but sometimes, the shoe went on the other foot...

David Letterman factsLate Show with David Letterman, CBS

21. He Had A Stalker

One of the darkest chapters of Letterman's career began in 1988. Margaret Mary Ray, a woman suffering from schizophrenia, began stalking him. Over the following months, Ray broke into Letterman's private tennis court and even took his Porsche with her three-year-old son in tow—but that was just the beginning of the nightmare.

The Vampire Diaries FactsWikimedia Commons, Pujanak

22. He Pitied Her

Ray began breaking into Letterman's house. Over a period of several years, authorities caught Ray trespassing at Letterman's home eight times. All the while, Letterman had been making light of his predicament, frequently making quips about his stalker on his show. But while he liked to poke fun at the scary situation, Letterman was sure to keep Ray's name out of the papers.

In a moment of sincerity, Letterman said in an interview that he had sympathized with Ray. Anyone could see that she was struggling, and Letterman continually declined to press charges. He hoped she could get the help she needed—but sadly, her story has a tragic ending.

David Letterman factsShutterstock

23. Her End Was Heartbreaking

Though Margaret Mary Ray saw many ups and downs in her struggles with schizophrenia, she eventually took her own life in 1998. Letterman publicly expressed his sympathy after her passing, and his spokesperson said: "This is a sad ending to a confused life." Unfortunately, this wouldn't be Letterman's last encounter with a troubled fan.

Crazy funerals factsShutterstock

24. He Was Supposed To Take Over For Carson

While the Ray saga was unfolding, Letterman's career kept on moving upward. Everyone knew he was bound to claim the legendary 11:30 pm timeslot. Most people assumed that Letterman was a shoo-in to take over for Johnny Carson when he finally retired from The Tonight Show—but anyone who bet on it was in for a rude awakening.

Johnny Carson factsThe Simpsons, 20th Century Fox Television

25. But It Didn't Happen

In 1992, NBC shocked the late-night world when they eschewed their golden boy Letterman and gave The Tonight Show to Jay Leno instead. But don't feel too bad for Letterman—after a decade of success, he bailed on NBC and headed over to CBS to helm the Late Show with David Letterman. The move also happened to make him one of the best-paid stars on television. Not a terrible consolation prize. And that's not even the best part...

David Letterman factsGetty Images

26. Carson Preferred Him To Leno

People close to Johnny Carson revealed that the legendary comedian considered Letterman, not Leno, to be his true successor. In fact, the retired Carson would occasionally send jokes to Letterman for him to say in his monologue. Really clever fans might have been able to tell which jokes were Carson's because Letterman would give his mentor's iconic golf swing whenever he delivered one.

Secret Carson jokes were a bright spot on the Late Show as Letterman got used to this new format—but there was darkness as well.

Johnny Carson factsPixabay

27. His Staffer Came Face-To-Face With A Killer

When you do thousands of shows, some messed up stuff is bound to happen. Once, as part of an interview segment, Letterman correspondent Rupert Jee approached a man with shoulder-length dyed blond hair, sunglasses, and a Michael Jordan jersey. Jee attempted to draw attention to the man by yelling “Hey everybody, it’s Michael Jordan!”, but the man quickly shooed him away. It was a dumb bit—but Jee had no idea what he was getting himself into.

That man happened to be Ramón Arellano, a sadistic, high-level Mexican drug cartel trafficker who was in hiding in Los Angeles at the time.

David Letterman factsGetty Images

28. He Hosted The Oscars

Remember how a lot of celebrities kinda hated the irreverent Letterman? Well in 1995, against everyone's better judgment, Letterman got the nod to host the Academy Awards. What could go wrong when the guy who famously disrespects celebrities hosts the night where celebrities take themselves the most seriously? That night would end up going down in history...for all the wrong reasons.

Jerry Lewis FactsShutterstock

29. It Went Terribly

Unsurprisingly, the Academy hated Letterman's jokes, such as introducing Uma Thurman and Oprah Winfrey to Keanu Reeves ("Oprah...Uma. Uma...Oprah...Have you kids met Keanu?"). Critics claimed that Letterman didn't take the event seriously enough. Come on guys, what did you expect? I'm sure that was an awkward evening—but for Letterman, it could get a whole lot worse.

David Letterman factsGetty Images

30. He Nearly Died

So far, we've had celebrity feuds, infamous interviews, and a stalker. What are we lacking? A health scare! In January 2000, a routine checkup revealed chilling results. One of the arteries leading to Letterman's heart was almost completely blocked. He had to be rushed into an emergency quintuple bypass surgery, and CBS had to improvise for the next several weeks.

After airing reruns at first, CBS eventually brought back a one-time staple of late-night: Guest hosts. Finally, about a month after his surgery, Letterman returned to the stage for one of the most memorable shows of his career.

David Letterman factsLate Show with David Letterman, CBS

31. He Teared Up On Camera

Fans associate Letterman with many things, but sincerity is not one of them. That made it all the more special when Letterman brought almost his entire medical team up on stage upon his return. Clearly holding back tears, Letterman thanked each of his doctors and nurses, proclaiming: "These are the people who saved my life!"

With the health scare behind him, Letterman was finally free to finish his career in peace and quiet, right? Not even close...

David Letterman factsLate Show with David Letterman, CBS

32. He Had A Restraining Order Against Him

Letterman had had his problems with crazed fans stalking him, but what about the time he stalked a crazed fan? Ok, not really, but in 2005, a woman got a restraining order against him. She claimed that Letterman was secretly speaking to her through his show, sending coded messages. I don't know what's more strange—that she thought Letterman was talking to her, or that a judge believed her and gave her the restraining order.

Lawyers Screwed factsPublic Domain Pictures

33. Oprah Was One Of His Infamous Enemies

It's impossible to talk about David Letterman without going into his many celebrity feuds. For decades, one of the most infamous was with Oprah Winfrey. The pair of them hated each other for 16 years after Winfrey appeared on Late Night in 1989. Winfrey was one of those celebs who despised Letterman's interview style, and she later said being on his show "felt so uncomfortable to me that I didn't want to have that experience again."

But of course, Letterman and Oprah were bound to cross paths at some point.

Celebrities Changed Name StoryShutterstock

34. He Didn't Even Remember

Not including Letterman's Oscar joke, he and Oprah finally met again in 2005 when she came back on his show. The moment fans were really waiting for was in 2013 though, when Letterman went on Oprah's show and they talked about their infamous feud. Winfrey confessed that being on Letterman's show had been a "terrible experience." And how did Letterman respond?

He said he didn't even remember it. Oh well, at least he apologized.

David Letterman factsLate Show with David Letterman, CBS

35. He Made The Wrong People Angry

If any late-night host was going to receive dangerous threats, it was Letterman. In 2011, he made a joke about the demise of an Al-Qaeda leader. Unsurprisingly, an Islamist militant subsequently threatened to kill him. And I bet you can guess how Letterman responded: "State Department authorities are looking into this. They're not taking this lightly...They're questioning, they're interrogating, there's an electronic trail—but everybody knows it's Leno."

Fun Facts To Tell At Your Next PartyWikimedia Commons

36. His Son Was Nearly Abducted

Letterman could make light of almost any dark moment in his career, from feuds to threats to stalkers. One moment, however, was too disturbing for even Dave to joke about. In 2005, authorities uncovered a plot to abduct Letterman's 16-month-old son and ransom him for $5 million. Even worse, the perpetrator knew Letterman: His name was Kelly Frank, a house painter who'd worked at Letterman's home.

Thankfully, authorities foiled Frank's plan before anything could come of it, but it was a chilling reminder of the price of fame.

Said To Police factsShutterstock

37. He Had A Drinking Problem

Letterman has been sober for nearly 40 years, but only because he learned of drinking's brutal effects the hard way. He started when he was just 13 years old, and it slowly began to take over his life. He claims that by the end, he spent 80% of his time under the influence. Letterman was headed down a dark path, but he came to his senses and quit before he could cause any real damage to himself or others.

Deannie Best factsPixabay

38. His Marriage Had A Dark Side

After his first failed marriage and his contentious relationship with Merrill Markoe, Letterman's relationship with Regina Lasko seems like a long-awaited success story. They've been together for almost 35 years and married since 2009. But this was no fairytale love story. Letterman was hiding secrets—and eventually, they were going to come out into the cold light of day.

David Letterman factsGetty Images

39. He Shocked The World

The October 1, 2009 episode of the Late Show with David Letterman was one of the most infamous moments in late-night history. Letterman stepped out on stage and revealed that someone was blackmailing him. An anonymous person threatened to reveal that Letterman had had several extramarital relationships with his female employees—something he confirmed to be true.

It was a remarkable act of defiance and honesty, but that's just the start of the story.

David Letterman factsLate Show with David Letterman, CBS

40. He Busted His Own Blackmailer

Shortly before the episode in question, Letterman found a package in his car. It revealed his affairs and said the blackmailer would write a tell-all book if Letterman didn't pony up to the tune of $2 million. Instead, Letterman went straight to the authorities and personally took part in a sting operation to bust the guy. It turns out, someone from Letterman's own network had betrayed him.

David Letterman factsShutterstock

41. A CBS Producer Was The Culprit

The blackmailer turned out to be Joe Halderman, a producer on the CBS show 48 Hours. Apparently, he should have watched more of his own show, because the authorities caught him pretty much instantly. He pleaded guilty to all charges and served six months in lockup, plus probation and community service. His plan had blown up in his face—but even if he didn't get the money, Letterman still had to deal with the fallout.

David Letterman factsGetty Images

42. He Slept With Several Younger Staffers

After years of sneaking around, Letterman finally admitted to having several affairs with women who worked on his show. He carried out a relationship with the show's intern, Holly Hester, despite the massive difference in their ages. However, his most scandalous affair was with his long-time personal assistant, Stephanie Birkitt. That's where the details of Letterman's cheating start to get really wild.

David Letterman factsGetty Images

43. He Made His Ex Work For His Mistress

Letterman's breakup with Merrill Markoe wasn't exactly friendly, but after years of silence between them, she finally got a call in the mid-2000s. Letterman implied he wanted her to come do some on-camera bits for the show—but in reality, he had something far more twisted in mind: He wanted Markoe to write bits for a young intern named Stephanie Birkitt.

Markoe wouldn't realize what was really happening until much later: Letterman had brought his ex-girlfriend back to write jokes for his mistress.

David Letterman factsGetty Images

44. One Affair Cost Him Everything

The affair with Birkitt was eventually what sealed Letterman's fate. Birkitt didn't only work on the Late Show; she had another gig: 48 Hours. In fact, she actually lived with Joe Halderman in the months leading up to the blackmail attempt. Halderman had access to Birkitt's personal diary and emails, and he used them to try and extort Letterman.

David Letterman factsGetty Images

45. He Made Everyone Else Miserable Too

Letterman was unsurprisingly miserable after his affairs came to light, but at least he managed to make life miserable for everyone around him too. After every taping, Letterman would gather all of his writers to go over every aspect of the show they'd just finished. Then he'd bring writers and producers back to his office to They'd talk about anything for hours on end. One staff member described it as a hostage situation.

All because the prospect of going home and facing his wife terrified him.

David Letterman factsGetty Images

46. He Wasn't A Great Boss

To be fair, it's not like the Late Show was the most fun work environment to begin with. Although Letterman was close with his writers in the earlier years, he'd been doing the show for decades. He eventually became aloof and distant, and he came to dread even speaking to his writers. He spent almost all of his time hidden in his office and made the writers speak to him through Steve O'Donnell, the head writer.

Eventually, the writers had a saying: “You might get to meet him when you leave.” But that's not the worst of Letterman's behavior as a boss.

David Letterman factsComedians in cars getting coffee, Netflix

47. He Was Passive-Aggressive

Letterman was an infamously passive-aggressive boss. I guess the whole "holed up in his office never speaking to anyone" thing might've been a hint. He hated conflict, and he would never fire anyone. Instead, he would just completely freeze them out of the show until they eventually got the message. That's a horrible way for anyone to lose a job—but for longtime producer Barry Sand and head writer Steve O'Donnell, it was a particularly cold betrayal.

David Letterman factsWikimedia Commons

48. Crispin Glover Pushed Him Too Far

If you're going to dish it out, you've got to be able to take it in return. On one of the most infamous episodes of Late Night ever, Crispin Glover appeared in-character while promoting a movie. Anyone who's seen Back to the Future knows Crispin Glover's a bit of a weird guy, and Letterman was clearly unprepared for his bizarre antics. Eventually, Glover kicked within inches of Letterman's face, and the host had had enough.

Letterman just walked off the set of his own show right then and there. Safe to say, it wasn't his finest moment—but it got a whole lot worse than that.

David Letterman factsGetty Images

49. He Nearly Suffocated Richard Simmons

Maybe one of Letterman's most infamous feuds was with fitness guru Richard Simmons. Simmons appeared on Late Night and Late Show all the time, and the pair seemed to have a pretty close relationship—but that all crashed and burned after an appearance in 2000. Simmons was dressed as a turkey (just roll with it) and Letterman sprayed him in the face with a fire extinguisher (just roll with it). Unfortunately, the results were disastrous.

Simmons suffers from severe asthma, and the blast from the fire extinguisher resulted in a brutal asthma attack. Letterman made light of the incident, and Simmons was furious. He didn't come back on the show for over six years afterward.

David Letterman factsGetty Images

Sources: 1, 2, 3, 4, 5

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