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Bill Maher to Sean Penn: You'll Meet Castro but Not Trump?

By    |   Monday, 16 June 2025 10:41 AM EDT

On the latest episode of his "Club Random" podcast, Bill Maher had some sharp words for Sean Penn when the actor raised concerns about the host's recent dinner with President Donald Trump.

At one point during their wide-ranging conversation, which was more than an hour long, Maher asked Penn if he did "the right thing" by dining with the president.

"Absolutely," Penn responded. "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."

The Oscar-winner said that he hasn't been invited to the White House but suggested that he wouldn't necessarily accept an invitation if one were offered.

"It's a long flight," Penn said.

"Really, you'll meet with f****** Castro and Hugo Chavez but not the president of the United States?" Maher asked, referring to former Cuban President Fidel Castro and the former president of Venezuela.

"Yeah, I saw good results come out of some of those things," Penn replied.

When Maher interjected, Penn added, "I just personally wouldn't trust anything that was said in the room, including the personality."

"It's not a matter of trusting it, it's a matter of seeing it, a matter of experiencing it, a matter of knowing it," Maher said. "I'm telling you, there's a very different guy behind closed doors in a different setting."

Maher, a longtime critic of the two-term Republican president, had dinner with Trump on March 31 after the meeting was set up by country rock singer Kid Rock, who is a mutual friend of both men.

In April, Maher discussed the 2 1/2-hour dinner on "Real Time With Bill Maher," saying he and Trump had talked about the war in Gaza, Iran, and the president's third-term ambitions.

Penn said he watched Maher's report on the dinner, but he would have preferred if it were "less successful."

Maher disputed Penn's assertion that the dinner was a success, saying 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 said. "So, it wasn't successful."

Penn then suggested that Maher could have used "more brevity" when reporting the details of his dinner with Trump, suggesting that the host could have said, "He treated me fine" and left it at that.

After noting that Penn had a "bad attitude," Maher pointed out that with Trump, "it's all about personal relationships."

"I will get you an invite," he told Penn. "He's a star f***** in a way. I bet you he would like to meet you."

Nicole Weatherholtz

Nicole Weatherholtz, a Newsmax general assignment reporter covers news, politics, and culture. She is a National Newspaper Association award-winning journalist.

© 2025 Newsmax. All rights reserved.


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On the latest episode of his "Club Random" podcast, Bill Maher had some sharp words for Sean Penn when the actor raised concerns about the host's recent dinner with President Donald Trump.
bill maher, sean penn, donald trump
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2025-41-16
Monday, 16 June 2025 10:41 AM
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