‘Really? You’ll meet with f**king Castro and Hugo Chavez’

Liberal host Bill Maher pushed back against criticism of his dinner with President Donald Trump, essentially telling guest Sean Penn to look in the mirror.

The host of the Club Random podcast was speaking with Penn about his crossing the political divide and meeting with the president back in April, despite his long-held disagreements. The actor acknowledged that while Maher is “so smart,” he personally would never have sat down with Trump.

Maher called him out on the hypocrisy.

**WARNING: Language**

(Video Credit: Club Random Podcast)

“But you do, I hope, think I did the right thing to have dinner with him,” Maher asked when the subject of Trump came up again in the hour-plus long interview.

“Absolutely, you’re so smart,” Penn replied.

“Look, this is the president of the United States, whether we like it or not, doesn’t matter,” he added.

“I think that when you talked about it on the show that I would have preferred that I saw his mission or his will to have the dinner, I wish I would have seen it as less successful. Because you’re so smart on policy,” Penn said.

“Well, 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,” Maher noted.

Penn took issue with how Maher characterized his meeting with Trump, which was arranged by Kid Rock. He suggested the “Real Time” host could have used more “brevity” when relating the dinner to the HBO audience in April.

“I never felt I had to walk on eggshells around him,” Maher recounted in his monologue at the time. “And, honestly, I voted for Clinton and Obama, but I would never feel comfortable talking to them the way I was able to talk with Donald Trump. That’s just how it went down. Make of it what you will.”

Twelve days ago, I had dinner with President Trump, a dinner that my friend @KidRock set up because we share the belief that there has to be something better than hurling insults from 3000 miles away. pic.twitter.com/KE2t2eyBkI

— Bill Maher (@billmaher) April 12, 2025

“Maybe I would have done some editing,” Penn told Maher, adding that he would not have accepted an invitation to meet the president because “it’s a long flight,” as he searched for other reasons in his thoughts.

“Really? You’ll meet with f**king Castro and Hugo Chavez, but not the President of the United States?” Maher shot back.

He continued to drop reality checks on the actor, who continued to grandstand about not meeting with a U.S. president.

“Would you go to the dinner? I think you’re crazy not to, not to want to see up close the person who’s this important in everybody’s lives for the last decade,” Maher added, telling Penn he was “just triggered” by the meeting.

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Originally from New York, Powers graduated from New York University and eventually made her way to sunny South Florida where she has been writing for the BizPacReview team since 2015.

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