25 Things You Never Knew About David Letterman

By

Smarter, quicker and funnier than any of his successors, even though he ‘retired’ from the circuit five years ago, David Letterman is still the undisputed king of the late-night show.

This is because, from 1982 to 2015, Letterman didn’t just change the game – he was the game, re-inventing the format and leaving others to follow the template he set.


With Letterman now back on our screens as the host of Netflix’s My Next Guest Needs No Introduction, we’ve listed 25 things you never knew about eight-time Emmy award-winner David Letterman, a legend of broadcasting.

25. He started out as a weatherman

David Letterman may be one of the biggest cheeses in late-night TV today, but he had to prove himself in some less-than-ideal media roles before landing the top position.

After graduating from university in Indiana in 1969, Letterman found his first job at WLWI, an Indianapolis television station.

ADVERTISEMENT

Here, Letterman acted as news anchor and sometime weatherman, a position he constantly undermined with some bizarre throwaway humour.

Letterman would predict hailstones “the size of canned hams” and report the weather for cities he made up on the spot (“Eight inches of snow in Bingree and surrounding areas”).

He also once announced that government officials had “removed the border between Indiana and Ohio making it one giant state (personally, I’m against it)”, after part of the on-screen weather map had been accidentally erased.

 

24. He was also a kids’ TV presenter

Letterman didn’t just slum it in local news before he became the toast of late-night TV in the 1980s.

Back in Indianapolis, Letterman was also a local radio talk show host, an occasional Indianapolis 500 reporter for ABC and, incredibly, a kids’ TV presenter.

Yes, the man who would in the 1980s revolutionise chat shows with his adult-oriented humour once had a gig fronting a TV series made just for children.

Letterman’s duties on WLWI also saw him host an early morning talk-show aimed at young people called Clover Power, in which he interviewed youth organisation members.

ADVERTISEMENT

23. He feuded with Oprah Winfrey for nearly 20 years

If you though that America’s TV powerhouses were all part of a club where they hung out and drank beer together on weekends, think again.

Not only are Letterman and Oprah Winfrey, two of TV’s biggest names, not friends, but the pair actually feuded for the best part of two decades.

 

It all began when Oprah appeared on Late Night in 1989, where she felt insulted by Letterman’s flippant tone and biting brand of humour.

After she refused to return to the show, Letterman turned Winfrey’s dislike for him and their ‘showbiz rivalry’ into a regular bit.

Fortunately, the two have since made up since Oprah agreed to be interviewed again by Letterman on the Late Show in 2005, in what he jokingly referred to as “the Super Bowl of Love”.

22. He had a stalker through the 80s and 90s

One unfortunate side-effect of fame is that celebrities occasionally have to deal with stalkers, and Letterman is no exception.

Letterman’s stalker ordeal began in 1988, when a woman, Margaret Mary Ray, was arrested for speeding around in the late-night host’s car, which she had stolen from his drive.

ADVERTISEMENT

Ray would from then until the early 90s frequently break into Letterman’s house and even camp out on his tennis court.

Eventually, Ray – who was schizophrenic – was arrested and ordered to serve 34 months in jail and in psychiatric institutions.

Sadly, Ray took her own life not long after her release; Letterman called her death “a sad ending to a confused life”.

 

21. His son was the target of a kidnap plot

With his stalker ordeal behind him, Letterman was at the centre of a much more sinister criminal plot in 2005.

This time, Letterman himself wasn’t the target, but his son Harry, born in 2003 to Letterman’s now-wife Regina Lasko, was.

Kelly Frank, a house painter who had previously worked for Letterman, had planned to kidnap Harry and ransom him for $5 million.

Before Frank could carry out his plan, he was arrested and sentenced to ten years in prison.

Having escaped from prison in 2007 (before being recaptured) and then violating his parole in 2014, Frank was finally released from jail last year after an extended sentence.

ADVERTISEMENT

20. Al Qaeda once put a jihad on him

Letterman’s fame hasn’t just attracted stalkers and kidnappers over the years – even Al Qaeda wanted a piece of Letterman at one time.

In 2011, Letterman made a crack on one of his shows about the death of an Al Qaeda leader who was killed in a Pakistan drone strike.

 

One Al Qaeda militant responded by posting online a call for all American Muslims to cut out Letterman’s tongue and kill him.

Never cowed, Letterman instead took to his show to joke about the incident, saying “everybody knows it’s Leno”.

Letterman also said he was checking his “CBS life insurance policy to see if I was covered for jihad”.

19. He used to be a ‘horrible alcoholic’

Though he’s spent the vast majority of his time in front of the camera 100% teetotal, Letterman used to have a very different relationship with alcohol.

Having begun drinking around the age of 13, Letterman was, until the age of 34, a heavy drinker.

ADVERTISEMENT

Letterman has described himself as a “horrible alcoholic” up until 1981, the year before Late Night with David Letterman began.

According to Letterman, before he got sober, he “was drunk 80% of the time. I loved it. I was one of those guys, I looked around, and everyone else had stopped drinking and I couldn’t understand why.”

So, if you think you’ve seen Dave drink on his show before, it’s all an illusion: it’s always just apple juice in place of booze.

 

18. He once sent Conan O’Brien a horse as a thank you gift/prank

In 2015, as Letterman’s time on the Late Show was approaching the end, stars from all over Hollywood were going out of their way to sing Letterman’s praises.

Even Letterman’s fellow talk show hosts got in on the act: just prior to the old man of late-night’s departure, Conan O’Brien wrote an article in tribute to him in Entertainment Weekly.

Letterman, so touched by O’Brien’s words, decided to deliver a gift to his former chat rival: a horse not coincidentally named Dave.

The gift, however, turned out to actually be a present-cum-prank from ‘evil genius’ Letterman: an animal that required constant, expensive maintenance and that O’Brien would later call “crazy”.

In a 2017 interview with Stephen Colbert, Letterman’s Late Show successor, O’Brien revealed that he had ultimately donated the horse to an equine massage centre.

ADVERTISEMENT

17. He used his own money to pay Late Show staff when the show went off-air for four months

From November 2007 to February 2008, Hollywood was on shutdown as a result of a crippling writers’ strike.

During this time, films had their productions delayed and shows were taken off air or put on hiatus. One of them was the Late Show with David Letterman.

 

Facing the prospect of his entire staff going – like much of Hollywood at that time – without pay for the duration, Letterman instead decided to open up his own wallet.

For the four-month period that the Late Show was off-air, Letterman used his own money to pay the show’s staff in its entirety.

16. He’s insanely rich

The horse for Conan, the ability to pay staff out of his own pocket for months – what, if anything, could it all mean?

Well, clearly, it means that David Letterman is stinking rich, even by Hollywood standards.

ADVERTISEMENT

After earning as much as $35 million per year at the height of his late-night fame, Letterman is now worth an estimated $425 million.

It makes Letterman one of the richest funny people in Hollywood, with more money than box office titan Adam Sandler ($360 million) and his longtime chat show rival Jay Leno ($350 million).

 

15. He lives on a gigantic New York estate

The question on everybody’s lips when Letterman announced his impending retirement in 2014 was: what exactly was the former workaholic funnyman going to do with his time now?

After he finally departed the Late Show in 2015, Letterman simply seemed to disappear, with fans wondering what exactly the former TV host was up to.

Well, for the most part, Letterman was doing what any sensible retiree would do: kick back and enjoy retirement at home.

The only difference from most retirements was that, for Letterman, ‘home’ was a 108-acre estate in North Salem, New York.

Letterman bought the property in 1994 for $5 million. The mansion at the centre measures 8,000 square feet, and boasts seven bathrooms.

ADVERTISEMENT

14. His car collection is ridiculous

With a love for motors, all that money and all that space on his estate, it should come as no surprise that David Letterman has a particularly fine car collection kicking around.

At last count, Letterman has dozens of vehicles worth millions collectively, with just one of his vintage roadsters having a value of $2.7 million.

 

Letterman currently owns ten Ferraris, eight Porsches, four Austin Healeys, a Mercedes-Benz, a Jaguar, an MG, a Pontiac and a classic Chevy truck.

Letterman also owns a 1995 Volvo 960 station wagon, souped-up especially with a 380-horsepower engine and gifted to him by Paul Newman.

Letterman even appeared on his 2013 episode of Comedians in Cars Getting Coffee in the Newman car.

13. Mark Hamill is scarily obsessed with Letterman

Mark Hamill, who has appeared on Letterman’s shows several times over the years, is a big fan of the late-night host, to put it mildly.

From the moment the show began in 1982, Hamill – who bearing in mind had a pretty hectic life by this point as the lead of the Star Wars movies – would videotape every single episode of Late Night.

ADVERTISEMENT

Hamill did this for years, only stopping a short while after Letterman’s move to the Late Show on CBS, to the point where he had boxes of videotapes.

Hamill even kept a Letterman viewing journal and, when he was away from his Manhattan home, he would have a housesitter record each episode of the show for him.

Hamill first appeared on the show in 1983, as part of a sketch that saw him pretending to be in London promoting Return of the Jedi in order to avoid reappearing as a guest.

 

12. A CBS producer went to jail for blackmailing Letterman over his workplace affairs

With a stalker, an Al Qaeda death threat and a plot to kidnap his son, Letterman’s late-night career hasn’t been without its controversies.

Probably the most high profile of all Letterman’s controversial late-night moments, however, came in 2009.

It was the year in which Letterman admitted, live on-air, to having been the subject of a blackmail attempt over affairs he had had with his staff over the years, in particular with his personal assistant Stephanie Birkitt.

What’s less widely known is who it was that had attempted to shake down Letterman (to the tune of $2 million, no less): Birkitt’s former boyfriend, Robert ‘Joe’ Halderman.

Incredibly, Halderman also happened to be an Emmy-nominated CBS producer. He attempted to extort Letterman after he discovered Birkitt’s affair, and subsequently served four months in jail for it.

ADVERTISEMENT

11. The incident left Letterman severely depressed

Much as it might be difficult to believe of a man as publicly good-humoured as David Letterman, the host has suffered ups and downs over the years like anybody else.

 

In a recent bigoraphy, Letterman admitted that his public confession of infidelity in 2009 left him “in hell”.

Calling the incident akin to “having killed your family in a car crash”, Letterman added that he was “afraid my family was gone”.

In a 2015 interview with Rolling Stone, Letterman said: “I felt like I’d dug a bottomless pit, and I was falling into it”.

He told the magazine that the very public extramarital controversy was “easily the lowest point in my life”.

ADVERTISEMENT

10. He almost starred in Airplane!

David Letterman: movie star? Well, before the funnyman got into TV hosting, it almost happened.

Before Late Night, Letterman had a few acting roles, appearing in Mork & Mindy and The Mary Tyler Moore Hour.

 

One of the roles that Letterman tried out for but ultimately didn’t get was that of Airplane!’s Ted Striker, who was played in the 1980 comedy classic by Robert Hays.

In 1982, when Letterman was in his first year hosting Late Night, Airplane!’s writer-director team Jim Abrahams, David Zucker and Jerry Zucker appeared on the show.

They shared a clip of Letterman’s (failed) audition, giving viewers a glimpse of what could have been: the king of late-night playing the lead in a blockbuster comedy movie.

9. He had an emergency quintuple heart bypass in 2000

Letterman’s personal scares haven’t just been limited to threats against himself and his family during his time as a TV star.

ADVERTISEMENT

In 2000, Letterman underwent an emergency quintuple heart bypass after a check-up revealed a serious artery blockage in his heart.

This took Letterman off the air for over a month, in which time guest hosts, among them the cream of the Hollywood crop, were asked to fill in.

 

In Letterman’s absence, huge stars including Bill Murray, Julia Roberts and Robin Williams stepped in to cover for him on the Late Show.

Letterman later joked about the scare, lobbying on his return to the Late Show for Indianapolis to rename a freeway The David Letterman Bypass.

8. He’s considered one of the worst Oscar hosts of all time

It wasn’t all simply plain sailing for David Letterman after he broke into the mainstream.

Over the years, Letterman has had his off days, though no off day was quite so off as his March 27, 1995.

ADVERTISEMENT

It was the 67th Academy Awards, and Letterman – considered the natural successor to regular Oscars host Johnny Carson – was emceeing.

It wasn’t to be Letterman’s night, with jokes falling disastrously flat and bits that Letterman had borrowed from the Late Show failing to translate to the different format.

Letterman’s Oscars presenting stint has since gone down in infamy, with his regularly being called one of the worst ever by critics. Unsurprisingly, he hasn’t been asked back.

 

7. He once got NBC to air a rerun of Late Night redubbed by impressionists

In the early days, before he settled into a familiar format, David Letterman was renowned for a subversive and sometimes downright experimental comedy style.

There is perhaps no greater example of this than the episode of Late Night that aired on September 25, 1986.

It wasn’t a new episode – the show was a rerun of an episode that originally aired on February 25 – but something about it was certainly…different.

Somehow, Letterman had convinced NBC that it was a good idea to air a repeat of the February 25 show with the voices of everyone featured dubbed by impressionists.

It didn’t go unnoticed that the guests and Letterman himself all sounded a little unusual – NBC was flooded by calls from viewers of the rerun asking what on Earth was happening.

ADVERTISEMENT

6. A 1995 episode of his show inadvertently exposed a murderer hiding out in LA

In his three decades-plus as a late-night broadcaster, David Letterman somehow became inadvertently tangled up in a number of criminal investigations.

 

Creepier even than the Al Qaeda threat or the kidnap plot was what happened on a 1995 edition of the Late Show.

In a pre-recorded segment, comedian Rupert Jee went out and about in LA to interact with members of the general public, Letterman feeding him lines through an earpiece.

At one point during the segment, Letterman tells Jee to yell “Hey everybody, it’s Michael Jordan” at an overweight, long-haired man wearing a Michael Jordan jersey.

This man was Mexican cartel boss and suspected mass murderer Ramon Arellano Felix, who was hiding out in LA at the time.

Felix was shot and killed in 2002, allegedly at the behest of El Chapo.

ADVERTISEMENT

5. He’s a registered political independent

Famously private about his private life, Letterman’s insistence on battering all sides of the American political spectrum with gags has always made it difficult to parse what his personal politics are.

 

We do know that Letterman has been openly critical of Trump, leading some to believe that Letterman is just another stereotypical ‘Hollywood liberal’.

In fact, Letterman is a registered independent – though that doesn’t mean he’s been secretly voting Republican on us all these years.

As recently as 2014, Letterman admitted that although he’s registered to vote independently, he’d never voted for a Republican in his life.

4. Four out of five living presidents appeared on his farewell show

Thanks to his willingness to embrace all sorts over the course his career, Letterman has never been short of celebrity friends.

This became strikingly evident on May 20, 2015, during Letterman’s farewell show, which saw a number of famous faces pay tribute to the late-night host.

ADVERTISEMENT

Present at the final recording were comedy heavyweights like Jerry Seinfeld, Jim Carry, Steve Martin and Bill Murray.

Also there to say goodbye to Letterman – in a fashion – were George HW Bush, Bill Clinton, George W Bush and Barack Obama, or four out of the five living US presidents.

The ex-presidents all followed archive footage of Gerald Ford in reassuring viewers that “our long national nightmare is over”.

 

3. His Late Show send-off montage took six months to make

After 33 years spent building a reputation for himself as the king of late-night television, Letterman’s send-off always promised to be something special.

As well as celebrity cameos and a special message from the four presidents, Letterman also got a farewell song from “favourite band” the Foo Fighters.

The band played Everlong, the same track that Dave Grohl and co played on the show after Letterman returned from heart surgery in 2000.

As Foo Fighters did their thing, a montage of images and clips assembled from Letterman’s 33 years as a late-night host played.

The epic highlight reel was precisely edited to the music, with the assembly of footage having taken months to put together – six in total, with editing beginning in November 2014 and ending in May 2015.

ADVERTISEMENT

2. He has chronic tinnitus

In 1996, William Shatner made an appearance on the Late Show that was momentous not just because Letterman had finally gotten William Shatner in the room.

During his appearance on the show, Shatner revealed that he suffered from tinnitus, a condition that causes a person to hear a persistent sound that isn’t actually there, often in the form of a ringing in their ears.

 

Shatner’s admission prompted Letterman to admit that he, too, had the condition – only he had no idea where he got it from.

While Shatner developed tinnitus after an explosion on the Star Trek set, Letterman just began ‘waking up’ with it.

“You awaken to the sound of your head”, Letterman told Shatner, playfully adding “I’m testing the emergency broadcast system in my head every day of my life.”

1. One guest appeared on his show 150 times

Back when he was the late-night master, David Letterman could get just about any guest he wanted.

That didn’t mean, however, that the Late Show host didn’t also have his favourite guests who returned to the show again and again over the years.

ADVERTISEMENT

Some people appeared on the Late Show dozens of times, with journalist Tom Brokaw making 49 appearances and actor and comedian Tony Randall appearing a whopping 70 times.

The person with the most Late Show appearances by far, though, is TV host Regis Philbin.

Regis appeared on Letterman’s couch 150 times between 1993 and 2015, once even – for some inexplicable reason – turning up dressed as Shrek.