Bill Maher roasts Sean Penn for meeting Hugo Chavez and Fidel Castro but not Trump

https://static.independent.co.uk/2025/06/16/11/07/Maher-Penn.png?width=1200&auto=webp&crop=3%3A2
image

Comedian Bill Maher lashed out at Oscar-winning actor Sean Penn on the latest episode of his Club Random podcast over perceived criticism of his decision to sit down for dinner with President Donald Trump in April.

Maher, often a sharp critic of Trump, unexpectedly met with the president after an invitation was brokered by their mutual friend Kid Rock. The host left the evening with a revised opinion, speaking glowingly of the commander-in-chief.

That provoked a backlash among liberals, with sitcom legend Larry David penning a scathing satire of Maher’s conduct for The New York Times entitled, “My Dinner with Adolf.”

Bill Maher and Sean Penn fall out over Donald Trump on the former’s Club Random podcast (Club Random)

Returning to the issue in his latest interview with Penn, Maher asked the actor: “You do, I hope, think I did the right thing to have dinner with him?”

Penn answered: “Absolutely, you’re so smart, you go there… Look, this is the president of the United States, whether we like it or not, it doesn’t matter. There’s a lot of reasons I was speculating that… it would be good for you to do that.”

From there, the star revealed that he had seen Maher’s subsequent account of the visit on his HBO show Real Time and wished that the ensuing coverage had been “less successful” for Trump.

Maher hit back: “It was less successful because I never stopped saying all the things I’ve always said about him. It would have been successful if he had somehow seduced me into supporting him. So it wasn’t successful.”

Penn, in turn, suggested Maher could have done more “editing” in relaying the details of the dinner, suggesting he had gone too far in offering a warm account of the evening, rather than saying simply: “He treated me fine, that’s that.”

Penn, a keen observer of global politics, has previously met with Central American communist leaders Fidel Castro, Raul Castro, and Hugo Chavez, and even the Mexican cartel boss Joaquin “El Chapo” Guzman for Rolling Stone, hoping to interest the latter in a possible movie project about his life.

Bill Maher dined with Donald Trump at the White House in April, inviting a liberal backlash (Getty)

However, Penn told Maher he would not sit down for dinner with Trump, adding: “The only reason I would not accept an invitation is… it’s a long flight.”

Incredulous, Maher reacted: “Really, you’ll meet with f***ing Castro and Hugo Chavez but not the president of the United States?”

“I, I, saw good results come out of some of those things…” Penn said defensively. “I just personally wouldn’t trust anything that was said in the room, including personality.”

Maher hit back: “It’s not a matter of trusting it, it’s a matter of seeing it, a matter of experiencing it, knowing it… I’m telling you, there’s a very different guy behind closed doors in a different setting.”

He went on to push Penn on whether he would accept a dinner invitation to the West Wing if he, Maher, helped facilitate it, to which the actor answered: “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.”

Clearly annoyed, Maher said Penn had a “bad attitude” and declared: “I’ll tell you this about Donald Trump and you don’t know it because you don’t go to dinners… It’s all about personal relationships… I will get you an invite. He’s a starf***er in a way. I bet you he would like to meet you.”