David Letterman: The Smart “Dumb Guy” from Indiana

Andrew Szanton
9 min readFeb 7, 2022

--

DAVID LETTERMAN made a living out of mocking himself as dumb, and loved showing footage from a camera operated by a chimpanzee on roller skates — but he’s a very smart man, and when he was in the late night TV game his rivals underestimated him at their peril.

David Letterman

Letterman went to an excellent high school in Indianapolis, Broad Ripple High, but until he was 16 he felt he had no real talents. He was tall and goofy-looking, and he hated his lips. “Duck lips,” he called them. He was very aware of the gap between his two front teeth. He looked like “a geek” — except that geeks were smart and David Letterman never felt smart. Geeks at Broad Ripple High took honors courses, and David didn’t make good enough grades for that.

The teenage David Letterman

In this floundering teenager stage, he had little sense of the adult world, but it seemed to him that anyone who made a good living, who was prosperous, would have to go to a lot of solemn meetings. Dave hated the sound of that. He was too restless to sit still in any meeting, and he was convinced that in serious adult meetings, with his smart aleck humor taken away from him, his stupidity would be glaring, and he’d be fired.

When he thought about things he really liked, he thought of watching TV with his parents. His father, Harry, was a florist. His mother, Dorothy, was a church secretary. On Saturday nights, Harry made popcorn and Dorothy and Harry and David sat together and watched “The Ed Sullivan Show.”

Harry was a big, noisy sort of guy, who liked the routines. Dorothy Letterman was much less impressed. When Ed Sullivan would say “Come on, now, let’s give a big round applause for…” Dorothy would observe tartly that it’s tacky to beg an audience to applaud; any good host should know that.

David also loved watching Johnny Carson host “The Tonight Show.” Harry Letterman would be in his underwear and David would be in his pajamas and they’d watch Carson together.

One time they took a fishing trip together and stopped at a bathroom which had a condom machine. David said to his dad, “Jeez, there’s a machine and it’s not candy and it’s not cigarettes…” And Harry said, “Ah… One day, you and I are going to have that talk.” “And we never did,” says Letterman today cackling as he remembers the good old 1960’s, when Dads were old-school.

David loved his Dad, but knew that Johnny Carson was much cooler than his dad, so it didn’t occur to David that he could ever be someone like Johnny Carson. Then in his sophomore year of high school, Letterman took a life-changing class in Public Speaking. The semester’s first assignment was to prepare, and then deliver in class, a five-minute talk about yourself.

Many students — especially the “smart” ones — found this a daunting thing to do.

David was all nervous and twitchy beforehand, but once the talk began, he found it easy. And fun. To his surprise and great pleasure, his talk went very well. Kids laughed. And Letterman thought: ‘If something this easy gets that kind of response, then I know what I want to do in life.’ But how could he get paid for talking and joking around?

He didn’t have the grades for Indiana University so he went to Ball State, where he majored in radio and TV journalism and worked for radio station WBST. He was fired for making cracks about classical music but helped start another campus station, WAGO.

Then he got a job as a weekend weatherman for WLWI, the NBC affiliate in Indianapolis. Letterman had no interest whatsoever in storm fronts and high pressure systems. He wanted to get on television and start to make a name for himself. And he did; Indiana was not used to a weatherman who’d say things like “Folks, they’re predicting hail stones the size of canned hams.”

He also liked to note: “I am just one heartbeat away from anchorman.” And he’d smile his goofy smile. Another time, while an aerial view of clouds showed on the screen, Letterman said “From space you can see the border between Indiana and Ohio has been erased. I’m not in favor of this.”

Letterman, the weatherman

Then one day David Letterman drove out to Los Angeles in a pickup truck, to “see if I could hit Big League pitching.” He had told his friends that he wanted to be a comedy writer in Los Angeles — but he didn’t really want to be a comedy writer. He used that line in case he bombed as a comedian and TV host.

Letterman had noticed that comedians who appeared on “The Tonight Show” often did shows at a place called “The Comedy Store.” So he drove around and found The Comedy Store, and got a job there as an emcee. Being an emcee at the Comedy Store was great training for him. He was surrounded by funny people, up-and-coming comics. He could soak in what they were doing, and try out some of his own material without the pressure of being a headliner. Everything was fluid, humor flying around. And no meetings.

Then, one miraculous day, he got his shot at “The Tonight Show with Johnny Carson.” And Johnny liked Letterman so much that he not only let him sit on the couch, but, after a while, invited him to be a guest host. It began to look like David Letterman might well succeed Johnny Carson as host of “The Tonight Show,” whenever Johnny decided to retire.

David Letterman, as a guest on Johnny Carson’s show

Then in 1980, Letterman got a network television comedy show — and it bombed. “The David Letterman Show” was a morning comedy show, which got good reviews from critics, but bad ratings, and was cancelled within a year. Letterman also noticed that, contrary to his expectations, people in TV had a huge number of meetings. Especially when ratings were bad; then the meetings were almost constant.

Letterman was quite upset about the failure of his show, but NBC executives told him not to worry, the time slot had not been ideal, and they were going to give him another chance. They did. In 1982, they launched “Late Night with David Letterman,” which followed Johnny Carson on NBC — and its success again made Letterman the heir apparent to the aging Carson. “Late Night With David Letterman” had a cult audience among college kids.

Johnny Carson got the biggest stars on his show. Letterman had to make do with second-tier stars, but that was something of a blessing because it encouraged him to develop his peculiar humor and create a show which didn’t copy Johnny Carson’s.

Letterman broke with show biz etiquette for network TV interviews. The standard back-and-forth was well-established.

HOST: Thanks so much for coming on the show.

GUEST: Thanks for having me.

HOST: What I love about your work is… How do you do that? You’re amazing.

GUEST: Thanks. Well, it’s like this. [Generic description of the work.]

HOST: And someone told me you went to the Virgin Islands and had a little adventure there?

GUEST: Yeah, you could say that… (The audience would giggle, and a long, self-deprecating anecdote began with a few ad libs tossed back and forth between host and guest.)

It was all very rehearsed, and safe. The anecdote would perhaps involve another celebrity. The conversations were funny but light. The host would smoothly guide the conversation, and enjoy it — or pretend to enjoy it — so there were no visibly awkward moments.

David Letterman was different. He cultivated the persona of an Indiana oddball, a hayseed in the big city. He would ask his guests pesky or offbeat questions, then smile a little weirdly at them, and milk long, awkward pauses. Some guests hated this. They appeared once, and vowed never to return. They, or their agents, would tell Letterman he was mean. That always surprised him; he thought he was just goofing around.

One night, Letterman had the character actor Christopher Walken on the show. Instead of asking “How do you prepare for a role?”, Letterman said ‘You always play a guy 15 or 20 degrees off center. Are you nuts?” The audience laughed. After Walken gave a partial answer, Dave followed up. “You’re not a psycho, are you?”

Christopher Walken

When Walken got off on a tangent about having studied with a fancy dance teacher with a pretentious name like Winona Van Buren, Letterman said “Me, too!” and gave us a toothy smile. It was different, and people liked it.

Sometimes, guests would complain to the show’s producer about some crack Letterman had made. “Give it back to him” the producers advised. “He loves that.” But giving it back to Letterman was harder than it looked, because he had already staked out his most vulnerable territory, and made it his home. You couldn’t tell Letterman he was immature, out of his league, or over his head hosting a network TV show — because those were running gags in his shtick. The “dumb guy” was the smartest one in the room.

But in 1992 when Carson was ready to step down from “The Tonight Show” NBC didn’t choose Letterman to take over the Tonight Show. Instead, they chose Jay Leno, and Letterman didn’t handle it very well.

Letterman signed a deal with CBS, and on August 30th, 1993 began doing his show on CBS. He became the late night show guy for CBS for many years.

David Letterman hosting his show on CBS

When 9/11 came, and New York was devastated, how do you host a comedy show? Letterman went on the air and did what so many people thought he could never do. He was serious. He was dignified. He was classy, and millions of people who watched his television show came away feeling better about their country. All of America saw what only Letterman’s good friends and a few perceptive viewers had seen; Letterman wasn’t a cut-up; he was a broadcaster whose specialty was comedy.

Letterman’s girlfriend Regina Lasko wanted to have a baby but Letterman felt he couldn’t be a father and also have his TV show. The show was his baby, and it wanted to be an only child. But in 2003, they finally went ahead with it. Regina gave birth to a son, whom they named Harry after David’s father. David adored the baby and felt like a total jerk for having resisted all this for 15 years. In 2009, Letterman and Lasko got married.

Regina Lasko and Harry Letterman

Some years later, Letterman had quintuple bypass surgery, and during his rehab period, one of his doctors told him quietly, “You don’t have to be this way. You don’t have to work so many hours.” Letterman thought about that, and decided it was right. He would not work so many hours. He would come in and do the show but not make so many of the decisions about what segments would be on the show, and who the guests should be. It also meant he could skip a lot of meetings.

By 2013, Letterman was 65 years old, and getting lifetime achievement comedy awards. He often wished he’d started a family earlier in his life. Reporters wanted to know how he enjoyed being a dad, and various people suggested he write a humorous book about fatherhood, as Bill Cosby had done. Letterman rolled his eyes and said, “I’m the 40 billionth person to have a child. I have no insights.”

Pride, pleasure and no insights

--

--

Andrew Szanton

Andrew Szanton is a memoir collaborator based in Newton, MA. If you or someone you know wants to tell a life story, contact him at aszanton@rcn.com.