Bill Maher Claps Back At Sean Penn Over Criticism Of His Meeting With Donald Trump
By Favour Adegoke on June 16, 2025 at 8:45 PM EDT
Bill Maher had strong words for Sean Penn after the actor took a jab at him for meeting with Donald Trump.
Penn, who is known for his intense leading man roles in film, said he would have declined such an invitation, although he conceded it was a "smart" move on Maher's part.
Bill Maher, however, didn't let the criticism slide despite how subtle it seemed. He reminded Sean Penn of his own past associations with controversial world leaders.
Bill Maher References Sean Penn's Past Meetings With Controversial Leaders
Sunday's episode of Bill Maher's "Club Random" featured filmmaker Sean Penn discussing a number of topics with the political commentator.
At some point, the two drifted into a conversation about President Donald Trump, during which Penn spent time criticizing some of the billionaire mogul's more controversial remarks, such as his threat to annex Canada.
The conversation then turned intense when Penn issued a subtle criticism over Maher's meeting with Trump at a White House event.
It began with Maher asking Penn whether he thought it was the "right thing" to have had dinner with Trump, to which the actor replied "absolutely," and added that Maher was "smart" to have done so.
However, Penn then mentioned that he would have turned down an invitation from Trump, which prompted a piercing retort from Maher about Penn's own past meetings with dictators.
"Really, you meet with f-cking Castro and Hugo Chavez, but not the president of the United States?" Maher said, per the New York Post.
Sean Penn Insists His Meetings With Controversial Figures Were Productive
In his defense, Penn stated that his meetings with leaders like Castro and Chávez were productive and that he would never trust Trump under any circumstances.
"I saw good results come out of some of those things," Penn said. "I just personally wouldn't trust anything that was said in the room [with Trump], including the personality."
Maher shot back by dismissing Penn's point, stating, "It's not a matter of trusting it," before going on to buttress his point with an example.
"It's like saying, 'I don't want this medical test because I don't want to know.' I want to know," Maher continued.
Bill Maher Says His Meeting With Donald Trump Wasn't 'Successful'
Despite their heated exchange, Maher and Penn eventually found some common ground regarding the impact of the meeting.
Penn had said that he desired Maher's dinner with Trump would be viewed as "less of a success," to which Maher quickly agreed, saying it was actually "less successful" since it didn't stop him from continuing to criticize the president publicly.
"It would've been successful if he had somehow seduced me into supporting him, so it wasn't successful," he added.
All About Bill Maher's Meeting With Donald Trump
Back in April, Maher told his "Real Time" audience about his surprising meeting with Trump.
He described the billionaire mogul as "gracious and measured," adding that Trump came across very differently in person compared to how he is typically portrayed in the media.
"I never felt I had to walk on eggshells around him," Maher said, per the New York Post. "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."
Maher went on to say that people were free to interpret the meeting as they saw fit.
"Make of it what you will. Me? I feel it's emblematic of why the Democrats are so unpopular these days," he added.
Bill Maher Slams Donald Trump's First 100 Days As A 'Sh-t Show'
Weeks after Maher's seemingly high praise of his meeting with Trump, he pivoted back to criticizing the billionaire mogul's administration over its performance during the first 100 days.
Without mincing words, the political comedian bluntly described it as a "sh-t show" in a quote for The Free Press.
"After 100 days, there are probably 100 things to legitimately hate," Maher said about Trump.
He then claimed that "disappearing people, the inefficiency of DOGE, ignoring the Supreme Court, and killing people overseas with drastic aid cuts" were some of the reasons why he believed that the administration had performed woefully.
Maher also mentioned that the "tariff-related market collapse," "third-term talk," "America no longer being seen as a safe place," and many other issues also contributed to his stance on the matter.
