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.
David Letterman Facts
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.
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.
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…
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.
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.
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.
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.
8. He Got Off To A Rocky Start
In 1971, David Letterman finally appeared on national TV for the first time…as 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.
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.
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.
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.
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.
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…
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…
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.
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.
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.
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.
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.
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…
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 stole his Porsche with her three-year-old son in tow—but that was just the beginning of the nightmare.
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.
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.
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.
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…
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.
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.
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.
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.
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.
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…
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.
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.
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.
35. He Made The Wrong People Angry
If any late-night host was going to receive death 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”.
36. His Son Was Nearly Kidnapped
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 kidnap 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.
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.
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.
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.
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.
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 cops caught him pretty much instantly. He pleaded guilty to all charges and served six months in jail, 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.
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.
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.
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.
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 just…talk.
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.
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.
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.
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.
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.