If you stayed up past 11:30 any time between the early 1980s and 2015, chances are David Letterman was right there with you. For more than three decades, he was the last voice you heard before bed; dry, unpredictable, and unlike anyone else on television.
He started out doing weather reports at an Indianapolis TV station before heading to Los Angeles in 1975. From there, he performed at The Comedy Store and picked up writing gigs, including a spot on Mary Tyler Moore’s variety show Mary. Then came Late Night with David Letterman in 1982, and late-night TV was never quite the same.
That show ran 11 years and earned five Emmy Awards and 35 nominations. Then on August 30, 1993, The Late Show with David Letterman debuted on CBS, filmed at New York City’s historic Ed Sullivan Theater. His first guest was Bill Murray, who famously spray-painted “Dave!” on Letterman’s brand-new desk. Billy Joel was the musical guest, and Paul Shaffer led the band.
The CBS run lasted 22 years. All told, Letterman became the longest-running late-night broadcaster in American television history. He collected 10 Emmy Awards from 52 nominations, two Peabody Awards, and a Kennedy Center Honor. As Jimmy Kimmel once told Rolling Stone, “No one from his generation influenced American comedy more.”
The Regret Behind the Success
With a résumé like that, you might think Letterman had no room for second-guessing. But in a 2012 interview with CBS, he was candid about the one thing he wished he had done differently.
“I wish I hadn’t been so gosh darn single-minded. When you have focus that tight you miss a lot of what’s going on around you.”
He was talking about fatherhood. Letterman had a son, Harry, and when asked in that same interview whether he wished he had become a parent sooner, his answer was simply: yes.
For years, he had believed it was an either-or choice. “I just thought when the topic would come up, I can’t do both,” he said. “I can’t try to have a successful television show and be a father.” Looking back, he realized that belief had been wrong. Becoming a parent, he found, complemented the rest of his life and changed the way he saw the world.
It is a thought that resonates beyond show business. When focus gets too tight, it can crowd out the people and moments that matter most. And those are not always things you can go back and reclaim.
More Words Worth Keeping from Letterman
Over the years, Letterman left behind a handful of other reflections that stick with you:
- “I have found that the only thing that does bring you happiness is doing something good for somebody who is incapable of doing it for themselves.”
- “My greatest fear in life is being dull. You can be great, you can be awful, but just don’t bother being dull.”
- “Anything worth doing is worth overdoing.”
- “Nothing, believe me, nothing is more satisfying to me personally than getting a great idea and then beatin’ it to death.”
Conan O’Brien, one of the many comedians shaped by Letterman’s example, put it plainly: “He’s been the North Star for me and for every comic of my generation.”
Not a bad legacy for a kid who started out reading weather forecasts in Indianapolis.




