Privacy, Openness, and a New Persona: Why David Letterman’s Interoffice Escapades Took This Longtime Fan by Surprise
Kelli Marshall / University of Toledo

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David Letterman, embroiled in scandal.

I have been a fan of David Letterman for 20 years. In high school and college, I tuned in periodically to both Late Night with David Letterman (1982-1993, NBC) and the Late Show with David Letterman (1993-present, CBS). Now, thanks to TiVo, I watch the talk show religiously, having rarely missed a broadcast in the past decade. Suffice it to say, David Letterman and I have a history together. This is one reason, I think, that the comedian’s recent admission about his interoffice sexual exploits surprised me.

There are certainly other, less personal reasons that this story was recently plastered all over television shows, newspapers, and the Internet, for example, the bizarre extortion plot attached to Letterman’s sexual relationships, the concern about potential sexual harassment in the Late Show workplace, and, of course, the media’s undying (and unhealthy) affection for sex scandals. But perhaps there is another, more implicit explanation that Letterman’s confession shocked not only me, but many of his fans, the social networking world, and the media. In short, the on-air persona that Letterman has created for himself over the past nine years–a more compassionate and more exposed host/philanthropist/heart patient/husband/father–grossly conflicts with his apparent actions behind the set. It is this disconnect that I’d like to consider further.

For much of his television career, David Letterman has thrived on sarcasm, irreverence, and aloofness–characteristics that have set him apart from other late-night comedy hosts like the emotional and politically charged Jack Parr, the laid back Johnny Carson, and the inoffensive, jovial Jay Leno. As well, Letterman’s cool indifference and sardonic tone have yielded several uncomfortable (yet unforgettable) interviews with stars, politicians, writers, and musicians. For example, in 1988 an annoyed Letterman derided American Splendor writer Harvey Pekar, calling his comic book nothing but “a little Mickey Mouse magazine, a little newsletter.” And in 1994, Letterman introduced Madonna thusly: “Our first guest tonight is one of the biggest stars in the world. In the past 10 years, she has sold over 80 million albums, starred in countless films and slept with some of the biggest names in the entertainment industry.” Madonna reciprocated this tacky introduction by dropping the word fuck over a dozen times during her interview.1


Reinforcing his detached persona during the 1980s and 1990s, Letterman only revealed tidbits of information about his personal life, and he kept himself out of the gossip spotlight. For instance, fans were aware that he was romantically involved with Merrill Markoe, a head writer and producer for Late Night. Also, it was widely known that Letterman was the victim of a schizophrenic stalker, Margaret Mary Ray, who repeatedly broke into the host’s Connecticut home, even once stealing his car. Additionally, the audience was familiar with Letterman’s inordinate number of speeding tickets and the cops who pulled him over. Finally in 1994, fans were introduced to Letterman’s mother, Dorothy, who served as his correspondent for the Olympic Winter Games in Lillehammer, Norway. But, that’s about it; so essentially, over nearly two decades as a public person, Letterman exposed a mere handful of specifics about his personal life.

However, in the year 2000, the self-described introvert began to share anecdotes about himself and his family. Moreover, he altered the content and tone of his interviews, especially those involving guests with children. This shift in nature ostensibly began on February 21, 2000, the evening Letterman returned to The Late Show after a month-long hiatus due to emergency quintuple bypass surgery. Forgoing his famous Top Ten list, the late-night host filled the stage of the Ed Sullivan Theatre with every member of the medical staff who cared for him during his stay at New York-Presbyterian Hospital. With typical humor, Letterman introduced the medical team: “Ladies and gentlemen, that woman at the end of the line gave me a bath!” Then, rather quickly all joking subsided, and a clearly choked-up Letterman offered these simple words to his audience: “Five weeks ago today, these men and women right here saved my life.”

Similarly, on November 4, 2003, Letterman shared with viewers another personal milestone, the birth of his son, Harry. Although some of his narrative was interspersed with characteristic jokes (e.g., he named his son Saddam), much of it was as frank and emotional as his bypass show. For example, he confided to his longtime sidekick, Paul Schaffer, that he “could never have imagined being a part of something that turned out this beautiful.” And before moving forward to his first guest, Letterman informed the audience of the rather touching story behind his son’s name: “My father passed away when he was 57. I’m 56 years old, and yesterday I had my first child. So I named him for my father. And his name is Harry Joseph Letterman. So God bless Dad, and God bless Harry.” Then, the new father proudly held up a picture of his one-day-old son.

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Letterman introduces audiences to his newborn son, Harry Joseph Letterman. (Nov. 2003)

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On his show, Letterman screens a personal home video of his son learning how to walk. (Jan 2005)

This calmer, personal, more introspective persona is reserved not only for the host’s pre-interview discussions about his son’s tree-house and soccer games, adventures on his Montana ranch, his (and Paul Shaffer’s) visits to Iraq, and his marriage to Regina Lasko, but also for his guests. For example, the host talks in depth with Julia Roberts about baby strollers and trips to McDonald’s (she’s never been, by the way).2 He also seeks parenting advice from Dr. Phil, Harry Connick, Jr., and other guests, explaining that he is having a hard time disciplining “Huff” (his nickname for Harry) and enforcing “the naughty chair.” And perhaps even more telling, the host who once deliberately offended guests with his disparaging, brutal humor now begs their forgiveness. Realizing that A-list celebrities like Meryl Streep, Susan Sarandon, Oprah Winfrey, and Madonna have been absent from the Late Show for nearly a decade because of his former behavior, Letterman has sincerely apologized on-air to each.

As some of my colleagues have pointed out, it’s not all that shocking that a man in such a powerful position as David Letterman would engage in sexual relationships with his female co-workers and subsequently cheat on his significant other. In fact, in this day and age such behavior is frequent among male public figures who carry some authority e.g., religious leaders, politicians, movie stars, professional athletes. But in general, late-night talk-show hosts (and comedians as a whole) have avoided this sort of philandering. Sure, Johnny Carson married multiple times, but there was never any public evidence of extramarital affairs. Likewise, to my knowledge neither Steve Allen, Jay Leno, Conan O’Brian, Craig Ferguson, Bill Maher, Jon Stewart, nor Stephen Colbert has been involved in a sex scandal. As a result, the uniqueness of Letterman’s situation certainly makes it surprising.

Moreover, comedians, satirists, and late-night talk-show hosts generally function as social observers and subversive truth-tellers. By drawing on contemporary culture and its goings-on, they are the ones who often deconstruct, expose, and challenge social expectations, rules, and hypocrisies; it’s not usually the other way around. 3 For example, most recently late-night comedians have riffed on the media’s fixation with swine flu, a senator who takes an Argentinean lover, and falsified footage from Fox News. A few years back, of course, jokes about Bill Clinton and Monica Lewinsky as well as Dick Cheney’s hunting trip (in which he accidentally shot his friend in the face) dominated the late-night circuit, with Jon Stewart exclaiming about the latter, “Thank you, Jesus.” The public, therefore, expects David Letterman et al to mock others’ foibles, fabrications, and scandals–not to be the butt of such jokes themselves.

But when considering why Letterman’s affair shocked Late Show fans, the media, and the social networking world, we again cannot discount the host’s recently revised image. Most late-night hosts have maintained the same on- and/or offscreen persona over the years. For instance, Maher is consistently snarky, interruptive, liberal-minded, and makes no qualms about his agnosticism or love of marijuana. Similarly, Leno has always come across as decent, fair, unpretentious, and a lover of cars as well as a devoted husband to his wife of thirty years. As well, O’Brien continually portrays himself as goofy, awkward, unabashedly Irish Catholic, and slightly bawdy but mostly wacky (see his masturbating bear and Triumph the Insult Comic Dog). Letterman, however, has “softened,” Oprah Winfrey points out in a recent appearance on the Late Show (Dec. 2005). There is now “a light in [his] eyes…a sweetness” that wasn’t evident before, Winfrey maintains (clapping wildly, the audience agrees). Indeed, over the past decade, Letterman has constructed a different persona: he has put aside some of his old ways, opting instead for a more involved, sincere, personal style of comedy and interviewing. As a result, Letterman’s affair and admission of dishonesty do seem at odds with his progressive modification, which again, theoretically makes his announcement, especially for fans, a rather unanticipated one.

Image Credits:
1. David Letterman, embroiled in scandal.
2. Letterman introduces audiences to his newborn son, Harry Joseph Letterman.
3. On his show, Letterman screens a personal home video of his son learning how to walk.

  1. The Museum of Broadcast Communications describes Letterman thusly: “a number of guests found him to be a mean-spirited interviewer and some celebrities claimed he was adolescent at best, highly offensive at worst.” []
  2. Other instances of Letterman’s newfound openness are as follows: On September 22, 2003, Letterman describes his encounter with a black bear which was wandering through the kitchen of his Montana home. This story gives way to several other narratives about Letterman’s adventures on his ranch (e.g., he was thrown from his horse, he survived another bear invasion). In December 2004, Letterman and Paul Schaffer spend Christmas in Iraq. Both talk openly about their memorable experience when they return to the air in January 2005.( This is apparently the fourth time the duo performed for the troops but the first time they both spoke at length about their travels.) In March 2005, Letterman humbly thanks on-air the police force of Chouteau, Montana, for arresting a man who was allegedly plotting to kidnap Letterman’s son and nanny. On April 26, 2007, Letterman, who rarely makes public appearances outside his own show, goes on Live with Regis and Kelly to welcome back Regis Philbin who had undergone his own bypass procedure. Similarly, in September 2007, Letterman surprises fans and makes another public appearance, this time on The Oprah Winfrey Show. Letterman’s interview, filmed in Madison Square Garden, served as Oprah’s fall premiere extravaganza. The television hosts discuss young Harry’s love of airplanes and bugs; and Letterman shares with Oprah’s audience several pictures of his son and family. In November of 2007, Letterman’s alma mater, Ball State University, names its new communications building after the talk-show host. Letterman attends the ceremony and gives a speech. When he returns to television, he not only speaks highly of his weekend experience, but also of his own college career at Ball State. In March 2009, Letterman shocks his audience with wedding news. Through a detailed story involving a pick-up truck, mounds of mud, and his curious child, Letterman informs viewers that in a small ceremony in Choteau, Montana, Letterman wed Regina Lasko, his girlfriend/partner of over twenty years and the mother of his child. Finally, since his son’s birth, Letterman has frequently shared stories, pictures, and videos of Harry. We know, for instance, that the father and son have built a tree house in their backyard, that Harry is a wise backseat driver, that Letterman attends soccer games and nursery school events, and that the two enjoy flying kites together. []
  3. For more on comedians and their social functions, see Shawn Chandler Bingham and Alexander A. Hernandez, “Laughing Matters: The Stand-Up Comedian as Social Observer, Teacher and Conduit of the Sociological Imagination, ” Teaching Sociology 37.4 (Oct. 2009): 335-52; and Murray S. Davis, What’s So Funny?: The Comic Conception of Culture and Society, Chicago: U of Chicago P, 1993. []


  • A celebrity’s congenial public persona can betray their personality off camera. Occasionally, as David Letterman discovered, this discrepancy backfires when lurid rumors, true or not, of, say, infidelity or drug use surface. Incidents like these foreground a double standard placed on public personalities. Why do many audiences demand more from them than they do from themselves? Can viewers mature and allow them mistakes?
    Letterman’s life in the spotlight must come with undue stress. Millions invite him into their homes nightly, and, as you enunciate, his effort in recent years to soften his on-air image is commendable in this harsh and cynical age. The Late Show host has even apologized on air for past wrongdoings. Another example besides yours involves the late Bill Hicks, comedian, friend, and frequent guest. In 1993 he censored a clean segment by Hicks only months before his succumbing to pancreatic cancer. To try and compensate for this needless decision – nothing in Hicks’ performance was relatively offensive – he recently invited Hicks’ mother onto the show and aired the stand-up’s “lost” routine. (This gesture was possibly motivated by commercial reasons as well, an appeal to a younger demographic many of whom idolize the comic.)
    The new Letterman remains suspect because, first, loyal watchers like you remember the sarcastic, lewd Letterman – the Madonna clip serving as a reminder – and, secondly, personality is something inherent and unchangeable. Letterman, like many stars, is acting, and if the schism between the real and the staged is too wide, shock is likely to ensue. What needs evaluation though is the attitude after the shock: “Why I’d never do that,” needs to become, “Who cares; no one is perfect.”
    Of course the double standard is no more apparent than with political celebrities, and Bill Clinton is the ultimate paradigm with falsities like “I didn’t inhale,” and “I did not have sexual relations with that woman,” explaining everything. Lying is inexcusable, and it put into question his integrity politically, but the acts themselves are commonplace, and it’s likely the viewer is just as guilty of similar perpetrations.
    Many audiences know more about celebrities than they do their immediate family, another reason for alarm over this fixation on personalities’ personalities. The reaction to juicy gossip on Letterman or Clinton is symptomatic of an unforgiving culture; it’s time for a change toward acceptance no matter how shocking.
    Thanks, Kelli, for a great read!

  • Ahhh, I completely forgot about Letterman’s invitation to Bill Hicks’s mother. What a perfect example of the host’s attempt to shift/soften his persona. Thanks so much for the reminder (and for reading), Sean.

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  • I loved this article. I love Dave, and my personality has also been influenced by him. I gotta also mention Warren Zevon’s last appearance on the Late Show before he dies when Dave dedicated the entire show ton that night to Warren to sing and talk. You also forgot to mention the most touching speech ever following the September 11th attack that Dave delivered on the 17th of sepember 2001. In addition, his tribute episode following the death of Johnny Carson in which he delievered a monologue sent by Johnny Carson in the weeks prior to his death, and had Peter Lessaly and Doc on the show. He talked about how much he owes to Johnny for his career. I cried throughout the show eventhough I had never seen johnny any where outside youtube!!

  • Hello — indeed, Letterman’s post-9/11 show was touching, but I have to say that Jon Stewart’s will always stand out to me more:;2001. Thanks for reading!

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  • Kelli, thank you for this great article! I too have been a fan of David Letterman for nearly twenty years. It was during my senior year of high school that the world was treated to the original “WAR FOR THE TONIGHT SHOW” , aka The Late Shift, between Mr. Letterman and Jay Leno. But for me, the recent “Office Sexcapade” story was one that did not completely surprise me and another layer to the complex world of David Letterman. While his recent on air persona has evolved to a “softer” and “gentler” David Letterman compared to that of the 80s and 90s, we have been fortunate enough over the last two years to have caught flashes of the Letterman of old. While fatherhood, 9/11, a brush with death and a desire to book Oprah, has certainly given Mr. Letterman fair reason to become more introspective, who can ever forget the drubbing he gave then Presidential Candidate John McCain for canceling a guest appearance at the last minute or the now infamous spaced out Joaquin Phoenix incident? The old Dave was always there. It was just hidden and used sparingly.

    As far back as I can remember, Mr. Letterman’s name has always been associated with his shows and headlines that dealt with both his private and public lives. In the 80s and 90s, the tabloids feasted on stories regarding his most famous stalker Margaret Mary Ray. In the 90s there was the aforementioned Late Shift War and in the ‘00s we have read and heard about the kidnapping attempt on his son, his bypass surgery, his 9/11 show and of course the sex-tortion attempt. As you mentioned, in general other late-night talk show hosts have not been involved with sex scandals, making the Letterman case unique, but I content that “uniqueness” is another item that simply sets him apart, whether intentional or not.

  • Hi again Kelli,

    Sorry I had to end the previous post the way I did. I needed to spilt my response in two because the system thought I was trying to SPAM, which I am not.

    So here is Part 2:

    While issues of office-affairs and cheating should not be taken lightly, this particular story brings us a glimpse of the world we live in today. While not pretending to be a model citizen, despite his softer image, we currently live a world where we hold celebrities to a higher standard and sadly find ourselves in a environment where the public wants to see those in power/success fall. Thankfully with the likes of Mr. Letterman, Conan, Jon Stewart et al, we also live in a world where we can poke fun at ourselves more than ever. So the two things that came to my mind when the news of the sex-tortion plot broke were:

    1. It is none of my business and why can’t the media making such a big deal of it?
    2. As Mr. Letterman quipped on the show: I know what you are thinking….Dave has sex?”

    Thanks again Kelli!

  • This article reminds me of a David Brooks Op-Ed from the NYTimes in October, 2009 (the URL is pasted below); I’ll explain why after this is the case in a moment.

    First—this is a very charming response to Letterman’s most recent life events, very candid. I realized in reading it how this is what reality TV strives to achieve, as well as the ultimate aspiration of the serial—that we may, over time, see real people really change, and that we may feel some personal relationship to said people and empathy for their situations over a prolonged period of time. Reality TV attempts this effect in ephemeral, superficial ways. The only “real” reality is, in fact, on stage with our TV hosts and personalities to whom we’ve grown accustomed as members of our own families. Watching David Letterman grow into an empathetic individual, into a father, over decades—that’s compelling; it’s cinema.

    Regarding the op-ed: As a member of the film industry, I am continually troubled by the apparent impossibility of fidelity for those in it. As noted in this article, Letterman’s transgressions seem all the more disturbing because of his observable change of character in recent years (for the better). Yet I recall David Brooks in his article on Jonze’s WHERE THE WILD THINGS ARE—an article explicating the divergence between the philosopher’s and the psychologist’s conceptions of character. The latter, in fact, denies the possibility of “character” being at all viable. Rather than any one man/woman evidencing their specific characteristics in everything they do (re: “Jon is honest,” or “Jane is courageous”), psychologists today suggest we are all just aggregates of a number of warring beasts. These beasts each have strengths and weaknesses that prevail in certain arenas (re: “At work, Jon is honest. At home, he is not,” or “With her husband, Jane is courageous. With her father, she is not”). Scripted television depends on the philosopher’s definition of character, particularly in daytime programming. But when the subject at hand is a real human being, such as David Letterman, we’re obligated to remember that we all have our “shadows,” in a Jungian sense. Letterman seems to have brought many of his shadows to light, but the shadow never truyl goes away.

  • Hi, David.

    First, thanks for your nice comments on my post! You’re right about “the old Dave.” It is still there; it is DEFINITELY still there as is evidenced by his “drubbing of John McCain,” as you put it. The feisty, caustic Dave has also shown up throughout the entire NBC/Leno/Conan debacle, and it is obvious — unabashedly obvious — that Letterman reveled it. In fact, I discuss that further on my own blog here:

    At the same time though, I still think the late-night host has replaced a great deal of his harshest sarcasm, irreverence, and aloofness with a calmer, personal, more introspective persona. Note, for example, his appearance this week on LIVE WITH REGIS AND KELLY in which he speaks openly about his fractured marriage and his willingness to “put the thing back together.” (I examine this on my blog as well As well, many times now, the second segment of the LATE SHOW is devoted not to poking fun at politicians, stars, etc., but to cute little anecdotes about his son and himself, most recently about their adventures with balloons at Party City. =)

    So, right. As you so nicely remind us, the “old Dave” isn’t gone, but he has indeed merged with a “new Dave,” which as Clara above points out, makes for some quite “compelling cinema.” Thanks again for reading and commenting!

  • Hi, Clara:

    What a fascinating article by Brooks — thanks for sharing! The idea that we don’t have one thing called character but “a multiplicity of tendencies inside, which are activated by this or that context” is both troubling and refreshing, isn’t it?

    As mentioned above in my response to David, I also appreciate your pairing Letterman’s shift in persona with the (failed?) objective of reality TV — and reminding us that, although it will try its damnedest, reality TV cannot fabricate what we’ve witnessed with Letterman over the decades. Thanks again for reading and commenting!

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