Far-left actor Sean Penn, a longtime poster child for Hollywood’s radical activism, was recently called out for his glaring hypocrisy during an appearance on Bill Maher’s Club Random podcast. Looking disheveled and unkempt—as if he had just wandered in off the street—Penn criticized Maher for meeting with former President Donald Trump, only to be swiftly shut down by the host. Maher fired back, pointing out Penn’s shameless history of cozying up to brutal dictators like Fidel Castro and Hugo Chávez while refusing to engage with a democratically elected American president.
“Really, you meet with f—ing Castro and Hugo Chavez, but not the president of the United States?” Maher retorted, exposing Penn’s absurd double standard. The actor, who once infamously interviewed Castro and praised Venezuela’s socialist regime under Chávez, now clutches his pearls at the thought of sitting down with Trump—a leader who actually put America first, secured the border, and delivered historic economic growth.
Penn’s selective outrage is a perfect microcosm of the liberal media’s deranged obsession with Trump. While they fawn over socialist tyrants who suppress free speech, jail dissidents, and destroy economies, they treat a successful American president like a pariah. The hypocrisy is staggering. The same Hollywood elites who lecture Americans about “democracy” and “decency” have no problem legitimizing murderous regimes—so long as they push leftist ideology.
Maher, to his credit, didn’t let Penn’s sanctimony slide. “But you do, I hope, think I did the right thing to have dinner with him,” Maher pressed, highlighting the importance of dialogue—even with political opponents. But Penn, like so many on the far left, would rather live in an echo chamber than engage with ideas that challenge his worldview.
Meanwhile, Trump continues to dominate the political landscape because he speaks for millions of Americans ignored by the coastal elite. His policies brought jobs back, strengthened national security, and exposed the media’s relentless bias. While Penn and his ilk virtue-signal from their ivory towers, Trump fights for the forgotten men and women of this country—the ones Hollywood despises.
🚨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
The liberal media’s refusal to hold figures like Penn accountable reveals their true agenda: silencing dissent and propping up narratives that serve the left. They’ll gladly platform dictators but demonize a president who actually delivered results.
h/t: Steadfast and Loyal
