Conan O’Brien might not be the first comedian you think of when it comes to political digs — he’s more famous for his self-deprecating humor, absurdist sketches, and that glorious red hair. But during the 2025 Oscars, even Conan couldn’t resist slipping in a quick jab at Donald Trump, using the critically acclaimed film Anora as his comedic springboard.
As Anora racked up its wins throughout the night, O’Brien saw his opening and took it. “Anora is having a good night. Two wins already,” Conan said, pausing for effect. “I guess Americans are excited to see somebody finally stand up to a powerful Russian.” The joke, landing with a roar of laughter and applause in the packed Dolby Theater, was a sly swipe at Trump’s recent — and highly controversial — meeting with Ukraine’s president, Volodymyr Zelensky.
With that one line, O’Brien managed to capture the strange mix of political fatigue and cultural catharsis that often defines awards shows in these hypercharged times. In typical Conan fashion, it was quick, clever, and just sharp enough to leave a mark without overplaying its hand.
The Trump-Zelensky-Putin Triangle That Set Up Conan’s Joke
Conan’s crack didn’t come out of thin air. Just days before the Oscars, Donald Trump’s Oval Office sit-down with Ukrainian president Volodymyr Zelensky made international headlines — and not in a good way. According to reports, Trump used the meeting to berate Zelensky, dismiss concerns about Russia’s ongoing aggression, and bemoan how unfairly Vladimir Putin had been treated.
It was a surreal moment even by Trump standards — cozying up to Putin while strong-arming a wartime ally — and the backlash was swift. Political commentators, late-night hosts, and social media all lit up, with even traditionally conservative voices questioning Trump’s increasingly pro-Russian stance.
Against this backdrop, O’Brien’s Anora punchline became more than just a clever Oscars quip. It was a reflection of the broader discomfort many Americans feel about their leaders’ reluctance to confront Putin directly — and their eagerness to see someone, anyone, push back, even if it’s just a fictional sex worker in a Russian oligarch drama.
‘Anora’ Dominates the Oscars — and Becomes an Unlikely Political Metaphor
Anora, the surprise darling of awards season, had already captured the cultural imagination long before Conan worked it into his monologue. The film, which tells the story of a New York sex worker who falls in love with the son of a powerful Russian oligarch — only to have his family launch a ruthless campaign to annul their marriage — has been praised for its fearless storytelling and razor-sharp commentary on wealth, power, and the clash between personal freedom and systemic corruption.
The movie’s success gave O’Brien the perfect setup for his dig. In Anora, the protagonist stands up to the might of a wealthy, connected Russian family — a bold stance that echoed the real-world desire for leaders to do the same. In a year where authoritarianism, oligarchy, and the shadow of Putin have been front and center in global politics, Anora felt eerily timely.
By the time Conan’s joke landed, Anora was already well on its way to becoming a cultural touchstone, not just for its storytelling but for the wider themes it tackled. That’s what made the quip so effective — it was a comedic bullseye, connecting Hollywood’s biggest night to the geopolitical drama playing out just beyond the red carpet.
O’Brien Stays Mostly Apolitical — But Not Entirely
Conan’s joke stood out precisely because it was the rare political moment in an otherwise relatively politics-lite ceremony — especially compared to last year’s Jimmy Kimmel-hosted Oscars, which took direct aim at Trump multiple times. Kimmel famously read aloud one of Trump’s scathing Truth Social posts during the broadcast, delighting the crowd by turning the former president’s criticism into comedy gold.
O’Brien, by contrast, has built his career on goofy, often self-deprecating humor, steering clear of the more pointed political satire embraced by his peers like Kimmel, John Oliver, or Stephen Colbert. So when Conan took aim at Trump — without even mentioning his name — it was all the more effective. It felt like a rare but well-earned jab, one that proved even the most apolitical comedians have their limits.
That’s not to say the ceremony was entirely politics-free. Actress Daryl Hannah made headlines with her impromptu salute to Ukraine while presenting an award, and the filmmakers behind No Other Land, which won for Best Documentary Feature, used their time on stage to criticize U.S. policy toward Israel and Palestine. These moments, combined with O’Brien’s joke, added subtle political texture to a show that, for the most part, stayed focused on celebrating film.
The Joke That Defined the Night
In a ceremony packed with heartfelt speeches, emotional tributes, and Anora’s sweeping wins, it was Conan’s understated joke that lingered longest in the minds of many viewers. It was a reminder that humor — especially the kind delivered with a knowing grin and a sharp twist — can sometimes cut through the noise better than any impassioned monologue.
O’Brien didn’t need to name Trump. He didn’t need to break into a political rant. With just one sentence, he acknowledged the elephant in the room, gave the audience permission to laugh at the absurdity of it all, and then moved right along to the next joke.
That’s the magic of Conan: smart, subtle, and perfectly timed. And in a year where the lines between politics, entertainment, and reality continue to blur, that little moment of levity felt like a breath of fresh air — and proof that sometimes, comedy really is the best commentary.