Video · 2026-07-25 · 42m · 12 moments

Conan O'Brien: Was America a Mistake?

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Claim◆

Americans should be able to criticize the founding fathers — learning more about history reveals nuance and mistakes, but questioning them doesn't mean renouncing the American experiment; it means being honest about it.

Conan argues that self-criticism is in the American spirit, and that learning more about the founders' flaws is part of an honest engagement with history — it doesn't mean rejecting the country.

transcript

Conan O'Brien: I admire any country or populace that is self-critical. That is one of my favorite qualities. And I do think there's a notion sometimes these days in the United States and we've had it before in the late 60s and early 70s that to love America you have to love everything about it and if you have any qualms at all you should leave. I think that's just not in the American spirit. And so we should look at ourselves critically and see what we love about some of these founding fathers and what we find deplorable or sadly lacking... The more you learn about anything, whether you're trying to learn the guitar or you're trying to study history, the more you realize you don't know and the more humbling it is. The more you learn about the founding fathers and about the start of our country, the more nuanced things can seem and the more you can question a lot of our mistakes. But I say go ahead and question them. It doesn't mean you can't love this experiment. It is an experiment. We can never forget that it's an experiment and we have to be honest with ourselves about our past. It doesn't mean we have to renounce the whole thing, but we just need to be honest about it.

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Context◆

The 250th anniversary of the American Revolution feels different from the Bicentennial — the Trump administration's appropriation of the celebration has made it partisan, so people who aren't part of that movement feel left out or unwilling to participate.

Conan contrasts the unified, joyful Bicentennial of 1976 with the divided, partisan atmosphere surrounding the 250th anniversary, attributing the shift to the Trump administration's political appropriation of the celebration.

transcript

Conan O'Brien: I was 12 or 13 the bicentennial. We had the bicentennial in this country as led by the great Gerald Ford. And I remember that very clearly. There was a mania. It was sort of just it felt very much like kind of an undiluted joy about the bicentennial. The tall ships came into Boston. I believe the queen visited. I mean, it was just everyone I think felt unified and good about it. Now we have the 250th and there is something interesting that's happening which is some people I think felt that the Trump and the administration kind of grabbed the 250th and made it more about their movement which meant that people maybe who weren't part of that felt left out or felt like they didn't want to participate. We're in a moment right now. We're clearly in a moment in this country and I think it's very hard for some people maybe to just say I'm really excited about our 250th when our current state is so divided.

Context◆

The 250th anniversary of the American Revolution lacks the unified national celebration of the Bicentennial because the Trump administration politicized the event, making it harder for those outside his movement to participate.

Conan contrasts the unified joy of the 1976 Bicentennial with the divisive atmosphere of the 250th anniversary, noting that the Trump administration's co-opting of the event alienated many Americans.

transcript

Conan O'Brien: Now we have the 250th and there is something interesting that's happening which is some people I think felt that the Trump and the administration kind of grabbed the 250th and made it more about their movement which meant that people maybe who weren't part of that felt left out or felt like they didn't want to participate. We're in a moment right now. We're clearly in a moment in this country and I think it's very hard for some people maybe to just say um I'm really excited about our 250th uh when our current state is so divided.

Claim◆

The more you learn about the founding fathers and American history, the more nuanced and humbling it becomes, and questioning their mistakes is compatible with loving the American experiment.

Conan argues that polarizing political extremes — cancel culture on the left and reflexive defense on the right — are a natural reaction to each other, and that genuine education about history produces humility, not certainty.

transcript

Conan O'Brien: The more you learn about the founding fathers and about the start of our country, the more nuanced things can seem and the more um you can question uh you know a lot of our mistakes. But I say go ahead and question them. It doesn't mean you can't love this experiment. It is an experiment. We can never forget that it's an experiment and we have to be honest with ourselves about our past. It doesn't mean we have to renounce the whole thing, but we just need to be honest about it.

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Mechanism

George Washington's dullness was a political asset — his boring, inscrutable nature meant he rarely said the wrong thing, and he was the indispensable man who kept the revolutionary army together.

Conan and Tom discuss how Washington's lack of charisma, terrible teeth, and inability to tell jokes made him a perfect leader — a blank slate onto whom others could project, and unlike Napoleon, he didn't say the wrong thing because he barely said anything.

transcript

Conan O'Brien: A dull leader is amazing. It's a tabula rasa. You can project anything onto Washington. He didn't say much. He I don't think he had a sense of humor at all... But isn't it brilliant that he was so boring? Because what you absolutely don't want is a Napoleon in this situation, right? He often didn't say the wrong thing because he didn't say much. And what's really funny is that he's surrounded by these brilliant men who've been trained in the classics who are very witty and they're these bon mots are flying left and right and he's just in the corner with his rotted teeth and ample hips. But what you can't take away from Washington is he was the indispensable man. He was very courageous and he kept that thing going. He kept that, you wouldn't want to spin the dial again without Washington leading these skirmishes. He really was the right guy at the right time.

gives example · 2

Claim

George Washington was the indispensable man — a boring, dull leader who was exactly what the revolution needed because he rarely said the wrong thing and held the army together through sheer courage.

Conan and Tom agree that Washington's dullness and physical unremarkability were assets: he was a tabula rasa onto whom others could project, and unlike Napoleon he never overreached, but his courage and resolve made him the right man at the right time.

transcript

Conan O'Brien: But what you can't take away from Washington is he, as has been said about him, he was the indispensable man. Uh he was very courageous and uh he he kept that thing going. He kept that, you know, you wouldn't want to spin the dial again without Washington leading these skirmishes. You wouldn't want to take that chance. He really was the right guy at the right time.

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Claim

Benjamin Franklin's greatest contribution to the American Revolution was his diplomacy — he secured French support, which was decisive for American victory, and his decision to side with the colonists was harder because he had spent so much of his life in London.

Conan and Tom explore how Franklin, the greatest diplomat America ever had, brought France into the war — driven by French hatred of Britain — and how Franklin's personal ties to London made his choice to back the revolution more profound than for the other founders.

transcript

Conan O'Brien: I do think many Americans don't realize the extent to which yes, George Washington's indispensable, but Ben Franklin, one of the most gifted — you could say the two most gifted of these four guys that you examined are probably Franklin and Jefferson. He's incredibly gifted. He's a great intellect, but he's also got a good sense of people. He's a great diplomat. He's the greatest diplomat we've ever had. And he brings the French in. He brings the French in. And if he hadn't brought the French in, maybe it would have still ended up working out for us, but it wouldn't have ended so decisively probably... And there's a direct cause and effect. If the French hadn't thrown so much money into helping us out and eventually helping us get our freedom, they probably aren't in the same kind of having the same kind of economic problems that directly lead to the revolution.

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Fact

America was the decisive beneficiary of French aid during the Revolution, and without Benjamin Franklin's diplomacy bringing France in, the outcome would have been far less certain.

Conan and Tom discuss how Franklin's greatest contribution was securing the French alliance, motivated entirely by French hatred of Britain, and that French financial support for the Revolution directly contributed to the economic crisis that triggered the French Revolution.

transcript

Conan O'Brien: I do think many Americans don't realize the extent to which yes, George Washington's indispensable, but Ben Franklin, one of the most gifted, you you could say the two most gifted of these four guys that you examined are probably Franklin and Jefferson. He's incredibly gifted. He's a great intellect, but he's also he's got a good sense of people. He's a a great diplomat. He's the greatest diplomat we've ever had. And he brings the French in. He brings the French in. And if he hadn't brought the French in, maybe it would have still ended up working out for us, but it wouldn't have ended so uh you know um decisively probably.

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Fact

Thomas Jefferson knew slavery was wrong — he wrote a condemnation of it into his original draft of the Declaration of Independence that Southerners forced him to remove — yet he perpetuated it to maintain Monticello, creating the defining moral contradiction of the founding.

Conan highlights the most striking fact from the Jefferson episode — that Jefferson wasn't simply a man of his time on slavery; he knew it was evil and wrote against it, but kept his plantation running on enslaved labor, embodying the central contradiction Americans must reckon with.

transcript

Conan O'Brien: The greatest fact that you guys brought up, I thought, in the Jefferson episode, was there are probably a lot of people who would guess that, well, this is the world that Jefferson was brought up in. He's a Virginian. Slavery is just part of their world. And he didn't know any better. And that's just not true. And that you said that he wrote in his original draft of the Declaration of Independence, he lambasted slavery and tore away at it and said this is a great evil and that other southerners made him take it out. But he knew better. He knew better. And as you pointed out, if you've been to Monticello, it's absolutely stunning. He's very proud of Monticello. And he probably loves Monticello more than anybody or anything and the only way he can keep it going is with slavery. So it's a terrible failing and I'm a big believer in we need to acknowledge those things while I think not throwing the baby out with the bath water and closing one's eyes to the fact that he was a remarkable writer, a remarkable ideologue, a remarkable politician, a remarkable president.

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Claim

The founding fathers knew slavery was wrong — Jefferson wrote a condemnation of it into the original Declaration — and their failure to act on that knowledge, even at the cost of financial ruin, is a profound moral failing that must be acknowledged without renouncing their achievements.

Conan argues that Jefferson's hypocrisy is especially damning because he knew better — he wrote an anti-slavery passage into the Declaration that was removed by other southerners — yet he chose to preserve Monticello through slave labor, and that Americans must hold both truths simultaneously: their greatness and their terrible failings.

transcript

Conan O'Brien: He knew better. He knew better. And as you pointed out, he, if you've been to Monticello, it's absolutely stunning. He's very proud of Monticello. and he probably as you said probably loves Monticello more than anybody or anything and the only way he can keep it going is you know with slavery. So, it's a terrible failing and I'm a big believer in we need to acknowledge those things while I think not throwing the baby out with bath water... It's hard not to to hold them to the standard that uh well that they demand for themselves. If they're talking about liberty and writing the Declaration of Independence, then of course they should be judged by those standards. Um it's not anachronistic to do so.

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Prediction

Statues should be made of durable soap that dissolves after 60 years, forcing each generation to actively decide whether to re-erect them — acknowledging that we can hold both admiration for historical figures' greatness and condemnation of their failings.

Conan proposes a thought experiment: make all statues from a durable soap that lasts about 60 years and then dissolves, so every generation must actively choose whether to put them back up — a middle ground between permanent veneration and iconoclasm.

transcript

Conan O'Brien: I have this idea that all statues should be made of a very durable soap that lasts about 60 years and then they dissolve and then you decide whether you re-erect it. And that should be every statue because the minute you carve someone in marble and put them up, especially in the modern era, the clock is ticking. And so why go through all the trouble of taking these statues down, make them a material that will dissolve and then you actively have to decide should we put it up again? I mean, that's the opposite of Mount Rushmore. That's there for 7 million years... These are remarkable people who I think so much of the writing and the ideas and also pragmatic at the same time in setting up a system that would until recent years withstand human frailty. It's just amazing that we were gifted this by these incredible people and then at the same time they can really disappoint and I think it's okay to hold both of those ideas and make the statues out of a somewhat durable soap and then decide whether to re-erect them after every 40 years as they turn into mush.

extends · 1supports · 1

Prediction

All statues should be made of a durable soap that dissolves after about 60 years so every generation must actively decide whether to re-erect them, rather than carving heroes in marble permanently.

Conan proposes a playful but substantive solution to the statue debate: make statues from a soap-like material that lasts about 60 years and then dissolves, forcing each generation to consciously choose whether to re-erect a monument rather than passively inheriting permanent ones.

transcript

Highlight slides

Self-criticism is the American spirit✦ from: Americans should be able to criticize the founding fathers — learning more about history reveals nuance and mistakes, but questioning them doesn't mean renouncing the American experiment; it means being honest about it.History rewards humility, not certainty✦ from: Americans should be able to criticize the founding fathers — learning more about history reveals nuance and mistakes, but questioning them doesn't mean renouncing the American experiment; it means being honest about it.The experiment demands honesty✦ from: Americans should be able to criticize the founding fathers — learning more about history reveals nuance and mistakes, but questioning them doesn't mean renouncing the American experiment; it means being honest about it.Bicentennial vs. 250th: Two Different Celebrations✦ from: The 250th anniversary of the American Revolution feels different from the Bicentennial — the Trump administration's appropriation of the celebration has made it partisan, so people who aren't part of that movement feel left out or unwilling to participate.The 250th anniversary politicized, unlike the Bicentennial✦ from: The 250th anniversary of the American Revolution lacks the unified national celebration of the Bicentennial because the Trump administration politicized the event, making it harder for those outside his movement to participate.Division drains patriotic enthusiasm✦ from: The 250th anniversary of the American Revolution lacks the unified national celebration of the Bicentennial because the Trump administration politicized the event, making it harder for those outside his movement to participate.Why the 250th Feels Different✦ from: The 250th anniversary of the American Revolution feels different from the Bicentennial — the Trump administration's appropriation of the celebration has made it partisan, so people who aren't part of that movement feel left out or unwilling to participate.History Education Breeds Humility, Not Certainty✦ from: The more you learn about the founding fathers and American history, the more nuanced and humbling it becomes, and questioning their mistakes is compatible with loving the American experiment.Political Extremes Feed Each Other✦ from: The more you learn about the founding fathers and American history, the more nuanced and humbling it becomes, and questioning their mistakes is compatible with loving the American experiment.

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