Rarely Known Details About David Letterman

The following article includes mentions of suicide.

If there was such a thing as talk show royalty, David Letterman would be wearing the crown. It's not a stretch to describe what he did on "Late Night" back in the 1980s as radical, revolutionary, and rebellious — name another talk show host who'd ever gotten laughs by stepping into a Velcro suit and jumping from a trampoline to stick onto a Velcro wall, hurling watermelons off a rooftop, or strapping a camera to a live chimpanzee for his "Monkey-Cam." Then there were such recurring bits as "Stupid Pet Tricks," his top-10 lists, and more.

Letterman changed the game when he jumped ship from NBC and launched his own CBS franchise, the "Late Show," which ran for more than two decades until retiring in 2015. That retirement, by the way, was definitely not one of those riding-off-into-the-sunset things. Just a few years later, in 2018, he partnered with Netflix for "My Next Guest Needs No Introduction," an ongoing series of long-form conversations with some of the world's most interesting people, including the likes of rapper-mogul Jay-Z, former U.S. President Barack Obama, philanthropist Melinda Gates, and Ukrainian President Volodymyr Zelenskyy, with that latter interview taking place on a Kyiv subway platform that had become a bomb shelter.

For a guy who's been a constant presence on TV screens for four decades and counting, what could there possibly be left to know about him? Plenty, actually, which will be revealed by reading on to discover the untold truth of David Letterman.

He bagged groceries during high school — and is still a pro

David Letterman went viral in 2023 when he posted a video on YouTube, shot during a visit to his hometown. In the video, Letterman returned to his roots by surprising shoppers in an Indianapolis supermarket to bag their groceries. "I spent a considerable amount of my life in a grocery store in Indianapolis," Letterman tells the supermarket's manager, recalling his teenage job bagging groceries. "I loved it," he added, "and if I can give something back to the marketing community, I would like to do that — but I don't have all day, of course." 

While the video is full of typically hilarious Letterman shtick — "By the way, did you hear today celery is free?" he told one shopper — it's also true that he has indeed retained a deep affection for his former gig packing up food purchases for customers. He made that clear during an appearance on "The Ellen DeGeneres Show," submitting to an interrogation by participating in the "Burning Questions" segment. 

Asked to single out his favorite pre-showbiz job, Letterman did not hesitate. "Workin' at the Atlas Supermarket, sacking groceries every day after school," he declared. "I loved it." Noting that the store's owner was like a surrogate father to him, Letterman also noted that some of his friends also worked there. "And every weekend we'd steal beer, and go out and drink the beer, and that was a great experience for me for four years," he reminisced.

He got his start as an Indiana weatherman and kids' show host

After graduating from Ball State University, David Letterman set his sights on broadcasting. Before long, he was hired by Indianapolis TV station WLWI. "I started when I was 20 years old in 1968 or something in Indianapolis," he recalled during a 2015 interview with "CBS Sunday Morning." 

Letterman's quirky sense of humor permeated his various gigs, which included hosting Saturday morning kids' show "Clover Power," doling out weather reports during news broadcasts, and hosting late-night movies. As CBS News recalled, Letterman turned everything he did into a comedy routine, once warning viewers to expect hail as large as canned hams and offering congratulations to a tropical storm that had been upgraded to a hurricane. That hilarity was also on display during his intro for an episode of "Clover Power" that wound up on YouTube. "Boy, oh boy, America, have we got a show for you," he quipped. "In fact, I'm surprised they didn't save this one and release it as a feature-length motion picture where you'd normally have to pay three or four dollars to get in and see it."

Letterman demonstrated he still had a knack for wacky weather forecasts when he crashed a 1988 edition of "Live at Five" to assist future "Today" show weather guy Al Roker in delivering his forecast. "These are important statistics, sunrise and sunset," Letterman joked, "if you happen to be a raccoon or a bat."

He co-starred with Michael Keaton and Mary Tyler Moore in a disastrous variety show

In the late 1970s, David Letterman made the move to Hollywood, hoping to establish himself in the Los Angeles comedy scene. He made his national TV debut when he was hired for the cast of "Mary," a 1978 variety show starring Mary Tyler Moore. Co-starring with Letterman were fellow up-and-comers, Michael Keaton and Swoosie Kurtz, along with comedy veteran Dick Shawn. Unlike her other shows, "Mary" bombed and was axed after just three episodes. The series' cancellation may have put Letterman out of a job, but he was also very likely relieved. That's evident from the pained expression on his face as he and the rest of the cast back Moore during a musical number from the show, an absolutely cringe-worthy performance of Paul McCartney's "With a Little Luck." 

"It was not on long, but I learned an awful lot," Letterman told Moore when she appeared on "Late Night" in 1983. "So did I: Don't do it again," she retorted.

Letterman and Keaton reminisced about their shared stint as song-and-dance men when the latter dropped by the "Late Show" in 2015. "Every Wednesday the choreographer would come in and teach us — Michael and myself and the rest of the cast — how to dance and [do] the big number. It was the worst day of my life for an entire summer," Letterman said, as reported by Entertainment Weekly. "It was unbelievably uncomfortable, was it not?" Keaton confirmed.

His bonkers morning show was a critically acclaimed bomb

After numerous appearances on "The Tonight Show" — impressing his idol, Johnny Carson, enough to eventually be tapped as guest host — in 1980, David Letterman headed to New York City to host a show for NBC. This was not the groundbreaking "Late Night," however, but "The David Letterman Show," which was broadcast live on NBC in a morning time slot. Featuring the same off-kilter tone as his future late-night show, the morning show struggled to attract daytime TV viewers more accustomed to watching game shows and soap operas. 

That said, "The David Letterman Show" set the template for his future success on "Late Night," with the morning show even originating such popular segments as "Viewer Mail," "Stupid Pet Tricks," and more.

While interviewing Letterman for "CBS Sunday Morning," host Jane Pauley referred to the brilliance of his morning show. "It wasn't brilliant, Jane," Letterman responded ruefully. "It was ... like standing on an overpass looking at a chain reaction collision, you know, that goes okay, nine cars, 10 cars. 'Oh look, it's 100 cars.' It couldn't have been more poisonous." Debuting in June 1980, the show was canceled just four months later. At the time, Letterman was certain that his career in network television was over. "I really thought that's it," he said. "You get one shot and away you go," Letterman said.

He holds the record for the longest uninterrupted stint on late-night television

While David Letterman may have feared he'd be returning to delivering weather reports in Indiana after the cancellation of his morning show, just over a year later, NBC tapped him as host of the "Late Show with David Letterman." Launching in 1982, the show aired in the little-watched 12:30 a.m. time slot following "The Tonight Show," which had previously been home to reruns. The show was a hit, building a devoted audience of college students and insomniacs, revolutionizing the talk show format in the process. 

When "Tonight" host Johnny Carson retired in 1993, and Letterman was passed over as his replacement (for Jay Leno, who ironically became famous for his appearances on Letterman's show), Letterman quit. Switching networks that fall, he made his debut as the host of "Late Show with David Letterman," which he hosted until retiring in 2015. Combining the years he spent on both shows, Letterman brought laughs to late-night viewers for 33 consecutive years, hosting a total of 6,080 episodes. As The Washington Post noted, that made him the late night's longest-running host ever, a record that has yet to be broken.

Shortly after walking away from the "Late Show," Letterman admitted he was still finding his footing after three-plus decades as a late-night host. "It's stunning what you find out about yourself when everything you've done for 33 years changes," he told Indianapolis Monthly. "It's like ice melting out from under you."

He still regrets his infamous stint as Oscars host

With the out-of-the-box success of "Late Show" for CBS, David Letterman's career was on fire when he was tapped to host the 1995 edition of the Academy Awards. As anyone who's ever hosted can confirm, hosting the Oscars can be an unforgiving gig, and Letterman stumbled at the outset with his infamous "Oprah-Uma" bit, introducing Oprah Winfrey to Uma Thurman to emphasize that their names are unusual and then adding "Have you kids met Keanu?" The joke bombed, which appeared to rattle Letterman as he continued to refer to it throughout the evening.

As the Los Angeles Times reported the following day, reviews were decidedly mixed. However, nobody was more critical of his performance than Letterman himself. In an extensive interview about his Oscars experience with The Hollywood Reporter, Letterman recalled the evening as an "explosion of excrement." Revealing the Oprah-Uma joke was a last-minute addition, and he recalled recognizing immediately that the joke flopped. "Because I felt like, 'I think someone's perspiring in this suit — oh, it's me.' I knew right away."

According to Letterman, he received a taste of how his hosting had been received while waiting to board a flight the next day. "I see people by the dozens holding up the New York Post with screaming headlines about how I had ruined the Academy Awards, and they were going to stop making movies for a year and rethink the whole thing," he quipped.

He produced a hit television sitcom

Viewers of the "Late Show with David Letterman" were likely aware the show was produced by Worldwide Pants, the production company David Letterman launched in the early 1990s. Worldwide Pants also produced "The Late Late Show," airing immediately after Letterman's show. The same year that the "Late Show" launched on CBS, another Worldwide Pants production debuted: "The Building," a sitcom headlined by Bonnie Hunt. Only five episodes aired before CBS pulled the plug. Letterman tried again in 1995, producing a new sitcom built around Hunt, "Bonnie," — which lasted a bit longer and was canceled after 12 episodes.

Letterman saw significantly more sitcom success in 1996 with the premiere of Worldwide Pants-produced "Everybody Loves Raymond," which won 15 Emmys (out of 69 nominations) during its hit nine-season run.

Interviewed by the Cleveland Plain Dealer, "Everybody Loves Raymond" star Ray Romano revealed that the whole thing came about when he made his "Late Show" debut in 1995. That appearance proved to be a pivotal one for Romano, who'd been climbing the rungs of the comedy ladder but was far from an established star. "I did five or six minutes of material. I had been doing standup full-time for about 11 years at that point. I was making a living at it," Romano recalled. "Following that show I got a call from Rob Burnett at Worldwide Pants saying that Dave liked my act and that he was interested in pursuing a development deal for a television sitcom."

He underwent quintuple bypass surgery

In 2000, David Letterman underwent emergency quintuple bypass surgery after an artery leading to his heart had become severely blocked. As The Washington Post reported, his family history — his father died from a heart attack when he was in his 50s — combined with high cholesterol levels led to an angiogram, which detected the problem and resulted in life-saving surgery.

That led him to ditch the signature cigars he puffed on during show tapings — no mean feat, considering he reportedly smoked 20 stogies a day. His new heart-healthy regimen also forced him to switch from regular coffee to decaf. "I've started drinking the decaffeinated coffee, and I wanna tell you there is no bigger waste of time than this stuff," he said on the show upon his return, his complaint punctuated by a musical jingle: "Decaffeinated coffee — it's what they're drinking in hell."

Looking back at his surgery in 2015, Letterman — then 68 — detailed how deeply the experience had affected him. "It restored my faith in human beings," he told the Tampa Bay Times. "I just assumed that if you're going to let yourself have open-heart surgery, it was going to be a flip of the coin, if you would survive or wouldn't survive. What I realized was, yeah, you're going to survive because the men and women doing these things know exactly what they're doing, they do it all the time and they care about what they're doing."

His favorite band is Foo Fighters

David Letterman has made no secret of his love of rock music. He's certainly had his favorites, an eclectic list that has included the likes of Counting Crows, Pearl Jam (he inducted them into the Rock and Roll Hall of Fame), and the late, great Warren Zevon. 

Yet atop that musical pantheon stands one band, led by one man: Dave Grohl and Foo Fighters. Making their network television debut on a 1995 episode of "Late Show," the band went on to make numerous return appearances over the years — and was the band hand-picked by Letterman to close out his final show. Arguably the group's most memorable appearance was during Letterman's first show back after heart surgery. As Letterman recalled during his final "Late Show," via The Hollywood Reporter, he specially requested Foo Fighters perform "Everlong" on that show. "It [was] meaningful during my heart recovery," Letterman said of the track. Unfortunately, Letterman learned the band was touring in South America at the time. Thinking that was that, he was then told, "That's all right. They canceled the tour. They are coming back to do the show. And they are doing the song that you asked for." Introducing them in 2000, he described the Foos as "my favorite band playing my favorite song."

That admiration is a two-way street. "I think we mean a lot to each other," Grohl told Entertainment Weekly of Letterman in 2015. "He's just genuinely a warm, sweet person."

He foiled a blackmail attempt by confessing to cheating on his wife

David Letterman had led a scandal-free life until 2010, when he dropped a bombshell during an episode of the "Late Show" to reveal he was the victim of a $2-million blackmail attempt over extramarital affairs he'd had with female staffers. He confessed it was true. "I have had sex with women who work on this show," he said, the audience laughing and applauding under the presumption it was a bit; it wasn't. Details emerged, revealing he'd slept with Stephanie Birkitt, a former intern on his show. Birkitt subsequently entered a relationship with CBS News producer Robert Halderman, who read her diary and learned of her ongoing affair with Letterman (who'd been in a long-term relationship with Regina Lasko, whom he married in 2009 after more than two decades together).

Letterman confessed all to his wife and went to the FBI. Halderman entered a guilty plea to a second-degree charge of grand larceny, resulting in a six-month jail sentence, 1,000 hours of community service, and five years of probation.

As Letterman told author Steve Young in his book, "Letterman: The Last Giant of Late Night," he fell into a deep depression about betraying Lasko and their son, Harry. "It was akin to having killed your family in a car crash," he said in an excerpt appearing in the Daily Mail. "I hurt a lot of people," he told "Oprah's Next Chapter." "I have nobody to blame but myself."

He's a car nut who co-owns an IndyCar racing team

Like his one-time late-night rival Jay Leno, David Letterman is obsessed with cars — the faster, the better. His collection of automobiles reportedly includes numerous vintage Porsches and Ferraris, among other vehicles. He's also been known to put the pedal to the metal; as he frequently told viewers, he'd racked up more than his fair share of speeding tickets over the years. Letterman found a way to indulge his need for speed without being pulled over by state troopers when he became co-owner of an IndyCar racing team, Rahal Letterman Lanigan, in 1996.

Growing up in Indianapolis in the 1950s, the famed Indy 500 race each Memorial Day was an ingrained part of the local culture that he and his family embraced, enjoying a backyard cookout while listening to the race on the radio. "It was like Santa coming Christmas Eve, there's a Memorial Day, you listen to the race," he recalled in an interview with NTT IndyCar Series.

As owner of the team — alongside former IndyCar driver Bobby Rahal and shipping mogul Mike Lanigan — Letterman has demonstrated that he's in it for the long haul. "Hard to believe it's been 20 years this year," Rahal told IndyStar in 2015 of Letterman's involvement. "Indy means so much to Dave, and I don't think he will ever miss the 500 no matter what he's doing."

His son was involved in a bizarre kidnapping attempt

Attempted blackmail isn't the only crime that David Letterman has had to contend with. Back in 2005, CBS News reported on a plot to kidnap Letterman's infant son, Harry. According to the report, Kelly A. Frank had been hired to do some painting at Letterman's home in Montana. Frank hatched a scheme to kidnap Harry and his nanny, with a plan to hold them both hostage for a $5 million ransom.

Thankfully, it never came to that. Frank blabbed about his plans to somebody described as an "acquaintance," who then took the information to authorities before the would-be kidnapper was able to set things in motion. Frank was arrested while working on a different property, and charged with felony solicitation, in addition to another charge, obstruction, for lying to authorities when questioned about his plan to kidnap Letterman's son. Frank was also hit with an additional charge of felony theft — for allegedly inflating his fee for the painting he'd done for Letterman.

He was sentenced to 10 years in prison but escaped in 2007. When he was apprehended, he was sentenced to 10 more years. He was released in 2014 but sent back to the slammer in 2015 for violating the terms of his parole. He was released in 2018 and then arrested the following year, this time for suspicion of misdemeanor assault, after threatening to kill someone. He returned to prison with his 2020 petition for parole denied.

He was dogged for years by a stalker claiming to be his wife

The strangest and saddest saga in the life of David Letterman involves Margaret Mary Ray, a deeply disturbed woman who spent years stalking him. She first made headlines in 1988 when she was arrested when she didn't pay a $3 toll — while driving Letterman's Porsche, which she'd just stolen, insisting to officers that she was his wife.

In subsequent years, Ray continued to harass Letterman and was arrested on numerous occasions while trespassing on the property of Letterman's Connecticut home. She ultimately spent 10 months in prison and then an additional 14 months in a psychiatric facility. Letterman responded with concern — for both his own well-being, and hers. "The thing is, she's insane," Letterman told the Stamford Advocate, via Tulsa World. "And you don't want to do anything to make it worse than it is." According to Letterman, he'd come to the end of his rope in how to deal with her. "It's been five years now, and I've tried a lot of things, and none of them have worked."

Eventually, she turned her attention from Letterman to retired astronaut Story Musgrave. When she was arrested for trespassing at his Florida home, reported the Los Angeles Times, Musgrave told authorities that she'd been stalking him for the past four years. In 1998, Ray took her own life when she kneeled in front of an oncoming train.

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The 'crazy' gift he sent to Late Night successor Conan O'Brien

When David Letterman retired in 2015, his "Late Night" successor, Conan O'Brien, wrote a hilarious and heartfelt tribute for Entertainment Weekly.

During a 2017 appearance on "The Late Show with Stephen Colbert," O'Brien revealed he'd heard that Letterman had been appreciative of the essay and would be sending him something as a token of his gratitude. That something turned out to be a horse, delivered in a truck to O'Brien's studio. "Oh, and guess what the horse's name is? Dave!" O'Brien recalled. Figuring he'd go with it, O'Brien found a stable where he could board the horse and then decided he'd learn how to ride it. "I go to get on it, and they say, 'I wouldn't get on that horse if I were you.' I say, 'Why not?' And they say, 'That horse is crazy,'" O'Brien said, revealing the horse had thrown two would-be riders and was deemed to be unrideable.

Letterman subsequently appeared on "Jimmy Kimmel Live!" and explained the whole thing was intended as a joke. "And the idea will be that he'll have the horse on the show, and the horse will take a dump on the show, and it will be hilarious," Letterman said, insisting he was shocked when O'Brien sent a note thanking him for the gift, revealing his plans to keep the animal. After boarding the horse for two years, O'Brien donated it to an equine massage school.