Conan O’Brien calls David Letterman “the North Star” for comedians of his generation.

John Stewart describes him as an “epiphany.”

Jimmy Kimmel says Letterman was more important to him than sleep, and he refers to Dave as “my Jesus.” 

Even if you didn’t watch late-night television throughout the ‘80s and ‘90s (back when DVRs didn’t exist), you knew Letterman. 

His biting ironic voice has become pervasive in popular culture, but you can’t truly appreciate the tumultuous rise to fame and notoriety of this weatherman from Indiana until you read his biography, “The Last Giant of Late Night” by Jason Zinoman.

Before we jump in… I get it. The irony isn’t lost on me that Letterman is famous for his Top-10 lists.

But let’s face it, you’re busy, I’m busy, so a Top 5 list it is:

1 – Surround yourself with people who are more talented than you

Especially those who compliment your skill set.

Letterman understood the power of collaborating with talented writers who value one another’s strengths rather than being intimidated by them.

In the early days of his talk show, all the greatest jokes and bits were not Dave’s at all; they were Merrill Markoe’s.

Merrill was a fantastic writer who didn’t love the stage. Dave always excelled at comedic timing, delivery and crowd work.

Together they were unstoppable. 

Markoe was Letterman‘s critical collaborator for the formative years of his television career, creating many essential parts of the show, including the famous “Stupid Pet Tricks” segment. 

“The show has always been somebody else’s voice. I have ultimate veto, but I haven’t had an idea since I was eleven, really. My viability as a creative voice is limited.”

– David Letterman 

2 – Know your strengths and play to them

Throughout his career, Letterman tried standup, hosting game shows, acting and even dancing. 

In 1979, he was offered the lead in Airplane!.

Playing aloof fighter pilot Ted Striker seemed like an apt fit for Letterman’s arched-eyebrow sensibility. But he wasn’t just relieved when he didn’t get the part; he was actually happy. 

In his cameo as an obnoxious motivational speaker on Mork & Mindy, you can practically see the discomfort dripping off Letterman (though the leisure suit might shoulder some of the blame).

He knew when he was in a role that was inauthentic to his skill set and said “I’ll never try that again.”

And he never did.

Letterman understood he was happier by showcasing his strengths compared to struggling through his less proficient talents.

3 – Embrace improvisation 

Letterman was a host at heart and loved crowd work.

The Late Show began exploiting these strengths with man-on-the-street interviews, impromptu calls to a woman working across the street from his studio and of course his playful banter with Paul Schafer.

One of the core tenets of improv comedy is “Yes, And.” The underlining principle being that you can innovate faster by affirming and building on ideas rather than shutting your teammates down.

Letterman knew that even bad ideas can be a bridge to better ideas. The team at Late Night always saw mishaps as opportunities.

Chaos wasn’t something to eliminate but rather something to relish in.

Letterman was light on his feet and able to break the fourth wall by adding an element of self-awareness. 

When a microphone didn’t work, Letterman would enter the picture, “You know, ladies and gentlemen, what you have witnessed is a screw-up.”

Some of the show’s greatest comedy came through improvisation. Letterman, like all great improvisers, knows that going off script often leads to magic. 

4 – Stand for something

Letterman’s entire career was about embracing his role as the underdog. 

He was anti-authority, anti-Hollywood, anti-TV and in some baffling interviews even anti-guest.

His audience loved him for it, and Letterman became one of the most fully realized characters on television—a beloved crank who was off-putting and entirely his own.

When pop star Billy Idol appeared as a guest on Late Night—with his black leather jacket, shock of white spiky hair and a playful scowl—he told Letterman that his songs were so popular that drug dealers were naming their products after them.  

Letterman injected some antagonism into the exchange and sneered, “You must be a very proud young man.”

Great comedians take a stand even if it’s divisive or polarizing. It’s taking a stand that creates love or hate. It’s taking a stand that forges fanaticism. It’s taking a stand that develops traction. 

Letterman wasn’t interested in lukewarm affinity.

He chose to be loved by a very passionate group of people who respected that he stood for something, and he was willing to risk being hated by some in the process. 

“You got a show and don’t have an opinion: What does that make you?”

– David Letterman 

5 – Celebrate your team’s wins along the way (sadly, Dave seldom did)

Letterman's gap-toothed grin was a welcome sight in homes across the nation from 1982-2015. Still, he was hardly a barrel of laughs off the air.

Those who worked with him say they knew a different man: an insecure hypochondriac whose fiery temper scared away many of those close to him.

For someone who started out as a no-name weatherman in Indiana, Letterman had plenty of career touchstones to feel good about.

He won numerous Emmy Awards. His idol, Johnny Carson, acknowledged that he was the rightful heir to the Tonight Show, and he was ultimately crowned the King of Late Night. 

The irony: Letterman was miserable even when his ratings put his show at No. 1. 

His self-criticism was reflexive and incessant. He was never truly comfortable unless he was seething with unhappiness.

When it comes to culture, it is said the fish rots from the head down.

Letterman seldom allowed himself to acknowledge the wins he and his team accomplished along the way, creating a toxic work environment ruled by anxiety and fear.

Nor did he care the effect his poor leadership had on his team. 

“This is a shitty place to work, but it will look good on your resume. Here’s a lollipop.”

– David Letterman 

Thank you and goodnight.

Letterman’s success and influence are built on pillars that we can all use to up our game at work.

We can also pay attention to his failings and avoid the pitfalls that come with the whirlwind of next-level success. 

You can still see the influence of David Letterman everywhere.

When James Corden shoots an entire episode in a stranger’s house or when Jimmy Fallon conducts an interview on helium or when Billy Eichner interacts with an unsuspecting passerby on the street, they are all walking in Letterman’s footsteps. 

Now, imagine what he could have accomplished with the right team culture behind the curtain.

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If you like this post, you’ll love Letterman’s biography, “The Last Giant of Late Night” by Jason Zinoman.

“Jason Zinoman’s writing is unbelievable, folks. The Smithsonian has already phoned and said they want a copy of his book for their time capsule. Stay home from work, and keep the kids home from school. History is being made.”

– David Letterman