Bill Maher Drops the Mic on Hollywood Hypocrite Sean Penn, His Past Haunts Him [WATCH]

Comedian Bill Maher addressed recent backlash over his April dinner with President Donald Trump, responding directly to criticism from actor Sean Penn during an episode of Maher’s Club Random podcast.

The exchange, which aired over the weekend, drew attention to the contrasting public behavior and political interactions of both public figures.

Maher, who has been a frequent critic of Trump on his HBO program Real Time, hosted the president for a private dinner that also included UFC President Dana White and musician Kid Rock.

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The meeting was arranged by Kid Rock and intended as a candid exchange across political lines.

During the podcast, Penn stated that he would not have accepted the invitation to meet with President Trump, prompting Maher to ask, “Really? You’ll meet with [expletive] Castro and Hugo Chavez, but not the President of the United States?”

Penn has met with several controversial international leaders over the years.

In 2007, he visited Venezuelan President Hugo Chavez in Caracas. In 2008, he conducted an interview with then-Cuban President Raul Castro and is also known to have met Fidel Castro during a trip to Havana.

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He traveled to Iraq in 2002 and to Iran in 2005.

In 2016, Penn admitted to meeting and interviewing Mexican drug kingpin Joaquin “El Chapo” Guzmán while the cartel leader was a fugitive.

That interview, he later said, was an attempt to open dialogue about the war on drugs.

Maher asked Penn directly during the conversation, “But you do, I hope, think I did the right thing to have dinner with him?”

Penn initially responded, “Absolutely, you’re so smart,” but qualified his position by saying he wished the meeting had appeared “less successful.”

“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.

Maher replied, “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.”

Penn countered by saying he personally wouldn’t have attended the dinner and that “there would be no purpose,” while also defending his previous meetings with controversial figures, saying, “I saw good results come out of some of those things.”

Maher responded, “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.”

He went on to compare avoiding such a meeting to someone refusing a medical test because they were afraid of what they might learn.

Penn agreed with the analogy but remained skeptical of the value in engaging Trump.

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

Maher said Trump was “gracious and measured” during the dinner and recalled that despite their long history of public disagreements — including a lawsuit Trump once filed against him — the meeting was civil and productive.

Maher noted that Trump did not ask for his support, nor did he request a public endorsement or photo.

“He gave me some hats and a very generous amount of time,” Maher said.

“I never felt I had to walk on eggshells around him.”

The two reportedly discussed policy topics such as immigration, law enforcement morale, and gender participation in sports.

Maher said they disagreed on certain points but that he appreciated Trump’s willingness to hear his perspective.

Maher, who has voted for Hillary Clinton and Barack Obama, said the meeting reflected his broader hope for more constructive dialogue in politics.

“I wanted to represent a contingent of centrist-minded people who believe there’s got to be a better way of running this country than hating each other every minute,” he said.

Maher also revealed that he brought a printed list of nearly 60 insults Trump had previously directed at him and had the president autograph it.

“He signed it with good humor,” Maher said.

As for whether their civility will last, Maher expects their public back-and-forth to resume.

“We’ll probably go back to insulting each other,” he said, but emphasized that the point of the dinner was to show that dialogue remains possible.

Both Maher and Trump reportedly agreed that many in their respective camps disapproved of the meeting.

“The people who don’t even want us to talk? We don’t like you,” Maher said, describing a rare moment of agreement between the comedian and the president.

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

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