Video · 2026-07-25 · 42m · 6 moments

Conan O'Brien's Brutally Honest History of the American Revolution

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Context◆

The 250th anniversary of the American Revolution is complicated by contemporary political division — the Trump administration's co-opting of the celebration made it feel less inclusive than the unifying Bicentennial of 1976.

Conan contrasts the exuberant, unified Bicentennial of 1976 with the tense, politicized 250th anniversary where the Trump administration's embrace of the celebration left many Americans feeling alienated.

transcript

Conan O'Brien: I was I believe 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. 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.

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Claim

The more you learn about the founding fathers, the more nuanced your view becomes — and that's a good thing; the American experiment requires honest self-criticism, not blind adoration.

Conan argues that genuine patriotism means embracing nuanced understanding of the founders' flaws and mistakes, not mindless celebration — the American project is an experiment that demands honesty.

transcript

Conan O'Brien: 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. And that's part of educating yourself. 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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Claim◆

George Washington's greatness came precisely from being boring — he was a tabula rasa who rarely spoke, had no detectable humor, and let the brilliant men around him shine, making him the indispensable man at the right moment.

Conan celebrates Washington's dullness as a strategic asset — unlike Napoleon, he didn't say the wrong thing because he barely said anything, and his physical unimpressiveness (bad teeth, ample hips, massive hands) made him a blank canvas onto which the nation could project its ideals.

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, you know, bon mots are flying left and right and he's just in the corner with his rotted teeth and I'm told also flared ample hips. I think he had kind of a big ass, but we'll talk about that another time. And massive hands. But what you can't take away from Washington is he, as has been said about him, he was the indispensable man. He was very courageous and he kept that thing going. You wouldn't want to spin the dial again without Washington leading these skirmishes. He really was the right guy at the right time.

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Mechanism

Benjamin Franklin's greatest contribution was his diplomacy — he was America's finest diplomat and his success in bringing France into the war was decisive, and the financial cost of that aid directly triggered the French Revolution.

Conan and Holland agree that Franklin's role in Versailles, cozying up to the French court, was the crucial pivot — French hatred of the British overcame their aversion to supporting a republic, and the money they poured into the American war bankrupted the French monarchy, leading directly to 1789.

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. 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. If the French hadn't thrown so much money into helping us out and eventually helping us get our freedom, they probably are not in the same kind of having the same kind of economic problems that directly lead to the revolution.

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Claim◆

Thomas Jefferson knew slavery was wrong — he wrote a blistering condemnation of it in the original Declaration draft that was removed by southerners — yet he chose to maintain it at Monticello, making him both an incomparable genius and a terrible hypocrite, and Americans must hold both truths simultaneously.

Conan highlights the central Jefferson paradox: he knew better than anyone that slavery was wrong (proven by his original Declaration draft), but he loved Monticello and could only sustain it through slavery. Conan argues we must honor his gifts as a writer and thinker while honestly confronting his moral failure.

transcript

Conan O'Brien: The greatest fact that you guys brought up 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. 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 as you said 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 not throwing the baby out with 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. It's a question for Americans that I am not qualified to opine on. How easy it is to do that — to have this man of incomparable genius who also has this great kind of moral blot and can the two be squared.

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Anecdote

All statues should be made of a durable soap that dissolves after about 60 years, forcing each generation to actively decide whether to re-erect them — because the moment you carve someone in marble, the clock starts ticking on their reputation.

Conan proposes a playful thought experiment: statues made of soap that lasts ~60 years before dissolving, so no generation gets stuck with monuments they didn't choose, and the decision to re-erect is an active, deliberate one.

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?

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Highlight slides

1976 Bicentennial vs 2026 250th✦ from: The 250th anniversary of the American Revolution is complicated by contemporary political division — the Trump administration's co-opting of the celebration made it feel less inclusive than the unifying Bicentennial of 1976.Why the 250th Feels Different✦ from: The 250th anniversary of the American Revolution is complicated by contemporary political division — the Trump administration's co-opting of the celebration made it feel less inclusive than the unifying Bicentennial of 1976.Two Anniversaries, Two Americas✦ from: The 250th anniversary of the American Revolution is complicated by contemporary political division — the Trump administration's co-opting of the celebration made it feel less inclusive than the unifying Bicentennial of 1976.The Power of Boring✦ from: George Washington's greatness came precisely from being boring — he was a tabula rasa who rarely spoke, had no detectable humor, and let the brilliant men around him shine, making him the indispensable man at the right moment.The Indispensable Canvas✦ from: George Washington's greatness came precisely from being boring — he was a tabula rasa who rarely spoke, had no detectable humor, and let the brilliant men around him shine, making him the indispensable man at the right moment.Jefferson Knew Better✦ from: Thomas Jefferson knew slavery was wrong — he wrote a blistering condemnation of it in the original Declaration draft that was removed by southerners — yet he chose to maintain it at Monticello, making him both an incomparable genius and a terrible hypocrite, and Americans must hold both truths simultaneously.The Monticello Trap✦ from: Thomas Jefferson knew slavery was wrong — he wrote a blistering condemnation of it in the original Declaration draft that was removed by southerners — yet he chose to maintain it at Monticello, making him both an incomparable genius and a terrible hypocrite, and Americans must hold both truths simultaneously.Hold Both Truths✦ from: Thomas Jefferson knew slavery was wrong — he wrote a blistering condemnation of it in the original Declaration draft that was removed by southerners — yet he chose to maintain it at Monticello, making him both an incomparable genius and a terrible hypocrite, and Americans must hold both truths simultaneously.

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