Sean Penn: I’d Meet with Castro, Chavez … But Not Trump

Bill Maher broke bread with President Donald Trump but never stopped skewering the world leader.

The host of “Real Time with Bill Maher” and “Club Random” angered some of the Left for dining with the real estate mogul in April. Fellow comedian Larry David insinuated Maher was a Nazi for that simple act.

The liberal Maher refused to back down, sharing some honest thoughts about the dinner with his flock. The friendly exchange didn’t deter Maher from mocking Trump on his dual platforms. 

He put a similar test to his newest “Club Random” guest, actor Sean Penn. The results were … surprising, to say the least.

Penn, a two-time Oscar winner, revealed he had yet to snag an invite to Trump’s White House. Nothing shocking about that.

What he said next, though, raised eyebrows.

“The only reason I would not accept an invitation is because I see no … it’s a long flight,” Penn said, trailing off.

“You’ll meet with f***ing Castro and Hugo Chavez — but not the President of the United States?” Maher fired back. Penn previously met with both world leaders.

“Yeah … I saw some good things come out of those things,” Penn answered.

“Did you really?” Maher asked. Penn provided no follow-up details but expanded on why he wouldn’t dine with Trump.

“I personally wouldn’t trust anything that was said in the room,” Penn said of any possible Trump dinner. “Including the personalities.”

“It’s not a matter of trusting it. It’s a matter of experiencing it,” Maher said.

🚨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

“Would you go to the dinner? I think you’re crazy not to … not to you wanna see up close the person who is this important to so many people’s lives for the past decade?” Maher added, suggesting his actions “triggered” Penn.

The actor didn’t deny it.

“[Trump] makes people crazy. He’s not making me crazy,” Maher said.

Penn worried that meeting with Trump would not yield anything positive.

“If I were, let’s say, representing a cause célèbre, say it was Ukraine … I would not fool myself that I was going to get anywhere with him. I know that I wouldn’t. I know that I would have no influence,” Penn said.

“That’s a bad attitude! You don’t know that. You don’t know anything,” Maher countered. “He’s a guy who frequently seems to go by what the last thing he heard was … It’s all about personal relationships [with Trump].”

During Trump’s first term, he worked with reality show superstar Kim Kardashian on crime and punishment issues. Those conversation led to the release of nonviolent offenders and an increased scrutiny surrounding prison reform.