Sean Penn, the Hollywood activist who hasn’t seen a razor—or a coherent political stance—in about a decade, appeared on Bill Maher’s Club Random podcast this weekend, looking less like a movie star and more like he wandered in from the back alley behind the studio. Between the cigars, the booze, and the incoherent takes, the whole thing felt more like a late-night dorm room rant than a serious conversation. But hey, welcome to modern Hollywood “intellectualism.”
The conversation took a turn when Maher called Penn out for what many of us have been pointing out for years: the glaring hypocrisy in his moral compass. See, Penn has spent years cozying up to every dictator and left-wing thug he could get close to—Fidel Castro, Hugo Chavez, even a bizarre meeting with Mexican drug lord El Chapo. But when Maher brought up his own meeting with President Trump, Penn suddenly got a case of selective morality.
Penn scoffed at Trump’s rhetoric, especially Trump’s tongue-in-cheek comment about annexing Canada. Because of course, sarcasm is lost on people who think Chavez was a misunderstood man of the people. Maher, to his credit, wasn’t having it.
“But you do, I hope, think I did the right thing to have dinner with him,” Maher said, referring to Trump.
Penn replied that he wouldn’t meet Trump if invited and wished Maher hadn’t even discussed the meeting on his show.
Maher’s reply? Brutal and dead on: “Really, you meet with f—ing Castro and Hugo Chavez, but not the president of the United States?”
🚨NEW: Bill Maher SCOLDS Sean Penn for saying he *wouldn't* have dinner with TRUMP🚨
MAHER: "You'll meet with f*cking Castro and Hugo Chavez — but not the President of the United States?"
PENN: "Yeah … if I were, let's say, representing a cause célèbre … I would not fool… pic.twitter.com/QNP9gcLwbZ
— Jason Cohen 🇺🇸 (@JasonJournoDC) June 15, 2025
Boom.
That’s the thing with these Hollywood leftists—they love to call themselves “resisters” while fawning over the very kind of authoritarianism they claim to despise. They’ll cheer on censorship, top-down government control, and political persecution as long as it’s dressed up in social justice slogans and comes with a Che Guevara poster.
Sean Penn is the poster child for this kind of delusion. He jets off to talk revolution with third-world strongmen, then refuses to sit down with the elected leader of his own country. And don’t forget—President Trump is the only modern U.S. president who didn’t start a new war. Meanwhile, Penn pals around with leaders who jailed dissenters and turned their countries into failed states.
Maybe it’s time for Penn to rethink his priorities. And while he’s at it, maybe wash his hair and buy a new shirt.