“Not Dead Yet” is Sasse and Stirewalt’s “shared project” and part of their legacy for their children and grandchildren. “I have a more finite number, but we all are numbering our days,” Sasse said.
“When we announced that @ConanOBrien would be one of our first podcast guests, the response was pretty uniform: How in the world do you know Conan?” Sasse posted on X. “(Truth is, I didn’t —but when you’re dying from cancer, it’s awkward for people to say no.) More seriously, Conan is a funny man, a rooted dad, and now—weirdly—a movie star.”
When we announced that @ConanOBrien would be one of our first podcast guests, the response was pretty uniform:
How in the world do you know Conan? (Truth is, I didn’t —but when you’re dying from cancer, it’s awkward for people to say no.)More seriously, Conan is a funny man, a…
— Ben Sasse (@BenSasse) March 6, 2026
During the conversation, O’Brien talked about his origins as a comedian, how fortunate he has been in his career, and the power comedy has to unite deeply divided people. He told Sasse and Stirewalt that he has never been motivated by money. Even before he was extremely successful, he was “happy as a clam.” What motivated him was making people laugh.
“Initially, all of us want to make our parents happy, I think, if you really go into the deepest psychological level,” he said, “and so every comedian starts, I think, trying to make their parents laugh and then their siblings laugh and then their friends in school laugh and that becomes a cache.”
When O’Brien realized he had a skill at making people laugh when he was “not good at so many things,” he doubled down on that ability.
“We’re Irish Catholic, Boston, and so there was a reticence about a lot of things,” O’Brien said of his family of origin. “A lot of things weren’t discussed, a lot of things were just kind of repressed, but the two places where we could go crazy was food and laughter.”
“For me, that was the pure dopamine hit,” he said, “seeing these people that I kind of revered—as a kid, you revere your parents—and you just see them laughing…it was a way to get to my dad.” The comedian explained that his family members did not verbalize their love, even though they all knew they loved one another.
“I’ve covered politics for a long time,” said Stirewalt. “It’s what I do. It’s how I got to know Ben, and in spite of all my best efforts, we became friends.” Stirewalt thinks there used to be more humor and “levity in and around politics” and wanted to know if O’Brien agreed.
The comedian did. “My impression is that it’s very dangerous to make a joke,” O’Brien said. “If you even say something sarcastically, it then becomes a pull quote in a negative attack ad. And that did not used to be the case.”
Sasse said, “I think that the politicians are less interesting people for lots of reasons.”
“But in addition, I think when you put cameras everywhere,” he said, “there’s always this attempt to go narrow but deep around your own audience, and so you can’t really say stuff against the tribe if they’re looking for confirmation bias. And so it becomes pretty boring in a hurry.”
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