Conan O’Brien Shakes Up the 2025 Oscars with a Bold Putin-Trump Joke: Hollywood Roars with Applause!
The 2025 Academy Awards were already shaping up to be a night to remember, but first-time host Conan O’Brien took things to another level with a sharp-edged joke about former President Donald Trump and his ties to Russian President Vladimir Putin. And oh boy, did the audience eat it up!
As the night unfolded, Mikey Madison’s film Anora was on fire, racking up win after win. O’Brien, ever the witty comedian, couldn’t resist making a pointed remark that instantly became the most talked-about moment of the night.
“You know, Anora is having a great night,” O’Brien quipped. “Yeah, that’s great. That’s great news. Two wins already. I guess Americans are excited to see somebody finally stand up to a powerful Russian.”
The audience roared with laughter and applause, fully understanding the underlying dig. While O’Brien never mentioned Trump by name, the implication was crystal clear. Hollywood, never shy about making a political statement, reveled in the moment as the legendary comedian soaked up the standing ovation. It was a classic Oscar moment, blending entertainment with sharp political undertones.
Trump Fires Back—But Loses Big at the Oscars
Just hours before the ceremony, Trump had taken to his social media platform, Truth Social, to rage about American priorities:
“We should spend less time worrying about Putin, and more time worrying about migrant rape gangs, drug lords, murderers, and people from mental institutions entering our Country – So that we don’t end up like Europe!”
But the former president had another reason to be fuming: The Apprentice, a controversial film about his early business years, was nominated for two Academy Awards—and lost both. Sebastian Stan, who portrayed Trump, lost Best Actor to Adrien Brody (The Brutalist), while Jeremy Strong, playing Trump’s infamous mentor Roy Cohn, lost Best Supporting Actor to Kieran Culkin (A Real Pain). A crushing night for the so-called MAGA movement. To make matters worse, The Apprentice had been shrouded in controversy from the start, with MAGA loyalists calling for a boycott and critics labeling it an “exposé on power, corruption, and the making of a political enigma.”
Trump’s War with Hollywood Continues
Unsurprisingly, Trump had already expressed his disdain for The Apprentice, calling it “fake and classless.” In a fiery statement following the film’s wide release in October, he ranted:
“It’s a cheap, defamatory, and politically disgusting hatchet job, put out right before the 2024 Presidential Election, to try and hurt the Greatest Political Movement in the History of our Country, ‘MAKE AMERICA GREAT AGAIN!'”
The Academy clearly wasn’t buying it, and neither was the Hollywood crowd who laughed and cheered as his film was shut out of the winners’ circle. This latest Oscars snub is just another chapter in Trump’s long-standing feud with Hollywood. He has repeatedly called the entertainment industry a “left-wing propaganda machine” and dismissed actors who speak against him as “out-of-touch elitists.” But despite his disdain for Tinseltown, his presence (or at least the idea of him) still looms large at these events, ensuring he remains a polarizing figure in pop culture.
More Political Moments at the 2025 Oscars
While O’Brien mostly kept the night focused on celebrating cinematic excellence, he wasn’t the only one bringing politics into the mix. Actress and activist Daryl Hannah made a passionate pro-Ukraine statement while presenting Best Film Editing, adding yet another layer of controversy to an already politically charged evening. Other stars also took the opportunity to use their platform, with acceptance speeches touching on topics from climate change to gender equality, reflecting the increasingly political nature of award shows.
The night wasn’t without its share of surprises either. An unexpected standing ovation for The Apprentice’s cast, despite its losses, suggested that while Hollywood might not be in Trump’s corner, there is still a fascination with his story—whether for better or worse. Meanwhile, O’Brien, ever the professional, effortlessly steered the event back to its primary purpose: honoring the art of filmmaking.
An Unforgettable Night in Hollywood
With its mix of glamour, cinematic triumph, and sharp political jabs, the 2025 Oscars proved once again why it remains one of the most electric nights in entertainment. Conan O’Brien delivered a masterclass in hosting, balancing humor, controversy, and reverence for the art of film. The glitzy ceremony not only celebrated Hollywood’s finest but also reinforced its role as a cultural battleground where entertainment and politics intertwine.
As the credits rolled on yet another unforgettable Oscars, one thing was clear: whether loved or loathed, Trump’s shadow continues to linger over Hollywood, ensuring that every awards season remains a spectacle of both cinema and controversy. And with O’Brien at the helm, it was an explosive, unmissable night that left audiences talking long after the final award was handed out.
