For those of us that watched David Letterman’s popular talk show Late Night with David Letterman, and later the Late Show, for the 33 years that these two programs were on the air with him as their host, we grew quite fond of his dry wit and charm. If all that we had to judge the guy on was his on-screen persona, we’d likely consider him to be an all-around swell fella. He could be cordial, funny, and even a bit sarcastic at times – but never did we get the impression that he was truly an awful person. Sure, he poked fun at celebrities at times and wasn’t afraid to buck heads with folks when it seemed called for, but at the end of the night, we still chuckled along to his jokes as we were lulled off to slumber.
But unfortunately, the David Letterman that we spent over three decades inviting into our homes through our television screens may not have been the likable personality that we thought he was. If we are to take the reports of some of those that know him personally seriously, then David is hardly the barrel of laughs that he presented himself as.
Late Night In 1982
David took the helm of Late Night as host in 1982, taking cues from Johnny Carson, his mentor and dear friend. In 1993, after NBC chose Leno to succeed Johnny Carson on his program, The Tonight Show, Letterman announced that he was leaving the network to host the Late Show with David Letterman over at CBS. He would remain as host of that program until 2015.
Letterman is also a television and film producer. His production company, Worldwide Pants, has produced such series as Everybody Loves Raymond, Ed, and The Late Late Show with Craig Fergusen. And since 2018, Letterman has hosted the Netflix offering My Next Guest Needs No Introduction.
Many other talk show hosts such as Conan O’Brien – his successor on Late Night – Stephen Colbert – his successor on The Late Show – as well as Jimmy Kimmel, Seth Meyers, and John Oliver have cited him as a significant influence. But perhaps they shouldn’t be holding him in such high regard.
Join us as we dissect some startling new revelations that paint David Letterman’s off-air personality in a whole new light. While our aim isn’t necessarily to stage some kind of character assassination, it seems as if David has done a pretty good job of doing that all by himself.
A Recent Biography Calls Into Question Letterman’s Character
Jason Zinoman’s 2017 biography of the late-night talk show host Letterman: The Last Giant of Late Night portrays him as far more self-loathing than we suspected. Zinoman paints a picture of David as an often miserable man who inflicted great pain on his staff.
Reportedly Letterman’s demeanor took a turn for the worse after July of 1995 when his program which for years ranked as number 1 in it’s timeslot dipped into second place behind Jay Leno’s The Tonight Show.
Viewers tuned into the NBC program when Leno managed to secure an interview with Hugh Grant following his arrest for soliciting a sex worker named Divine Brown. Following that landmark event, many viewers simply never returned to what they saw as Letterman’s acerbic on-air persona.
The Tonight Show and Nightline
As time went on, he went from being warm and inviting – albeit always a bit sardonic – to increasingly caustic as his comedy took a somewhat sadistic turn. On one evening in particular in 1995, after the Late Show trailed behind both The Tonight Show and Nightline, his rage became readily apparent to all who were watching.
A comedy routine that involved a life-size doll of himself sat in Letterman’s guest’s seat. Semingly spontaneously, Letterman punched the doll. The audience ate it up, and laughter filled the studio. The laughs didn’t stop as he struck the doll a few more times. Then the audience, all 580 members and all, fell into an uncomfortable silence as Letterman went into a full-on rage-fit as he repeatedly punched and slapped his plastic facsimile.
It was very clear that there was something dreadfully wrong with Dave that night.
Worldwide Pants
In a private yet candid conversation with Letterman, Rob Burnett, the head of Worldwide Pants and one of Dave’s most trusted allies, told him that people simply didn’t understand why he was behaving the way that he was.
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Anyway, Letterman’s wrath wasn’t all just directed towards himself. He became increasingly livid with just about everyone else he came in contact with as well – especially his staff.
David Letterman’s Antics
Burnett remained as executive producer, but following Letterman’s antics, their relationship had become somewhat strained. And although historically, he could manage his boss’ strange and often abrasive mood swings, all of that would come to an end when the two had a falling out. Things eventually got to the point where the two barely spoke to each other.
A longtime staffer disclosed that at that point, everything changed. He revealed to Zinoman that there comes a time when working for Letterman, no matter who you are, that he turns on you. It’s almost expected.
For example, a man named Tim Long, who worked as a head writer for Letterman’s show, grew so upset and frustrated by Dave’s constant put-downs and mood swings that he began chewing on soda cans and swallowing little bits of aluminum.
David Letterman Is Too Pushy
Then there was the time that the typically chill Paul Shaffer snapped at Letterman one night when Todd Rundgren sat in and played with the house band. Letterman kept trying to push Rundgren to do more than just the single number they had done in rehearsal. He seemed like he wouldn’t be satisfied until Rundgren relented.
Shaffer got so upset that he yelled at his bus in a pretty dramatic and explosive way. He became so embarrassed, however, that the moment had to be cut from the show before it aired even though Dave said that he was okay with it airing.
Letterman Was A Miserable Man Even When He Was No. 1
The ironic part about all of this was that Letterman was still unsatisfied even when his ratings put him at number 1 with late-night audiences. In 1993, he decided to part ways with NBC after the network chose Jay Leno to succeed Johnny Carson on The Tonight Show. That’s when he hopped over to CBS for his Late Show With David Letterman program filling the same 11:30 time slot.
At the time, CBS offered Letterman an unprecedented $16 million annual salary. That deal was pretty much a no-brainer for Letterman, who seized it and proceeded to crush the ratings of the once unbeatable Tonight Show.
NBC Talk Show
Even so, Letterman remained bitter and impossible to please. One producer told Zinoman that Letterman complained even from the beginning and that from there, things just continued to snowball downhill.
According to Paul Shaffer, things only got worse when he made the leap to CBS. He further expressed that Dave would find fault with just about anything regardless of how minor the perceived flaw in question was.
Rich Hall, one of the writers of Letterman’s NBC talk show, was disgusted by Dave’s demeanor when he appeared as a guest on his new program. Hall had just followed actress Andie MacDowell after she had just messed up her segment. In between shoots, Letterman evidently leaned into Hall and called MacDowell a few choice words that we’d rather not share in this video.
Connie Chung Says That David Is A Very Different Man Off-Air
Veteran Newscaster Connie Chung has worked at the majority of the major networks throughout her career which has spanned almost half a century. In 2020, she made an appearance on Los Angeles Magazine’s podcast The Originals. On that program she revealed some telling behind-the-scenes details about her relationship with Letterman.
In that interview, she even divulged that the two at one point shared mutual feelings for each other. But according to her, she only shared those feelings when it came to his humorous and charming on-air personality. She went on to explain that when the cameras aren’t rolling, he’s a very different sort of man – dark, and unhappy. She even called him a goyishe Kvetch, a Yiddish term for an ever-complaining type of person who gripes a lot.
Chung’s husband since 1984, Maury Povitch, says that he is well aware of Letterman’s feelings for his wife. He even claims that Letterman purposefully mispronounces his name out of spite for the fact that he married Chung.
Dave Admit’s He’s Difficult To Work With
When making a rare appearance on network television appearing on Ellen Degeneres’ talk show in 2019, Letterman said he stayed on the air so long because no one had the guts to fire him. He further expressed that he felt like he had stayed on television for about a decade longer than he should have.
The now 74-year-old who these days sports a big bushy beard – an apparent symbol of his retirement – warned Ellen that she needs to make sure to save enough energy and time for other things in life, something he never did while he was on the air.
Letterman admitted that for years, he felt like he was looking through the wrong end of the telescope as he put it, adding that there is far more to life than quizzing guests about their pets and careers.
David Letterman Abrasive Personality
While some say that Letterman’s smugness was always his greatest attribute, others found his style and personality a bit abrasive. And judging by this relatively narrow sampling of people who have known him personally over the years, it would seem as if Letterman’s off-air persona is a lot more astringent than we ever imagined.
But what do you think? Do you believe these fairly damning opinions of David Letterman that paint him as a cold, bitter, unsatisfiable grump, or do you think that perhaps people are looking back on the past through an unreasonably narrow lens? Let us know your thoughts on David Letterman and his decades-spanning tenure as a late night talk show host in the comments section below.
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