“The tough guy who never was” — Sean Penn calls Donald Trump “father's punk from Queens” on podcast

Academy award-winning actor Sean Penn has coined new monikers for President Donald Trump. During his latest podcast appearance on the May 13 episode of The Louis Theroux Podcast, the Mystic River actor opened up about the 47th President of the United States.

The conversation between journalist Louis Theroux and Penn, which took place a few months ago at the Hollywood actor’s Malibu home, also had Penn expressing his views on various world leaders like the President of Ukraine, Volodymyr Zelenskyy as well as the Russian President, Vladimir Putin.

On the topic of President Trump, Penn was emphatic. He described the President as,

“the tough guy who never was," and added about Trump: "He was his father's punk from Queens for a long time. You know, he was the tall Q-tip guy in school. He got into business, he got around a lot of real tough guys, gangsters.”

Sean Penn’s disdain toward the current administration is nothing new. In December 2024, while speaking to Variety about his close friend, Hunter Biden, Penn called the then President-elect Trump’s administration a:

“a clown show, a dangerous clown show”

Sean Penn’s impression of President Trump

The conversation around politics and political figures started when, right at the outset, Theroux asked whether the actor, who frequented New York City in the 1980s, had ever met the current President who, at the time, was a real estate mogul in the city.

Penn claimed he had indeed met Donald Trump, during a flight out of the city. According to Newsweek, the actor said about meeting Trump:

"I have briefly, very briefly, [met him] many years ago," adding that his first impression of Trump was: "Salesman."

Adding to his opinion about the President, Penn said,

“I think, you know, there's so much about President Trump, I mean, so much history, where, you know, he says things that people say, oh, that's never gonna, he usually really thinks what he's saying, even if it's a lie. You know, he doesn't differentiate between a lie and the truth. It's all about what's going to work for him.”

Sean Penn’s criticism about the current political climate

The Tree of Life actor also offered a critique of the general political atmosphere during his appearance on The Louis Theroux Podcast. Penn said,

“our political leaders in particular, I think, equal failure on both sides for the last, long period of time, in moving towards where we are in the culture.”

Penn was also critical of the activities of Trump and billionaire Elon Musk, who is currently serving as a Senior Advisor to the President. He said,

“When we talk about whether it's what Elon Musk is doing now for him, with him, I don't know if there's any thought behind it at all, except to value destruction of things, and people. And so, I can't associate that with any intelligence that's going to do humankind any good.”

Sean Penn on President Trump’s plans for Hollywood

Before his inauguration as the 47th President of the United States, Trump had announced a ‘Special Ambassadors’ program as part of his plans for improving the Hollywood film industry, in January, 2025.

According to Variety, the President declared that veteran Hollywood actors, Jon Voight, Sylvester Stallone and Mel Gibson would act as envoys on his behalf. Variety noted that the President took to his Truth social media page to write,

“It is my honor to announce Jon Voight, Mel Gibson, and Sylvester Stallone, to be Special Ambassadors to a great but very troubled place, Hollywood, California. They will serve as Special Envoys to me for the purpose of bringing Hollywood, which has lost much business over the last four years to Foreign Countries, BACK—BIGGER, BETTER, AND STRONGER THAN EVER BEFORE!

Trump continued,

“These three very talented people will be my eyes and ears, and I will get done what they suggest. It will again be, like The United States of America itself, The Golden Age of Hollywood!”

Sean Penn was asked to comment on the President’s plans for Hollywood on The Louis Theroux Podcast. He actor replied:

“It seems to me that what he's looking for in everything, and I say this because of what he has said that he's looking for, and is to control it all, and to make sure that the messaging flatters and does not question him, or his agendas. If any of them actually work to do that, then I would be very critical of that. You know, they're very talented men, actually. And some of them likable.”

Sean Penn’s criticism of the Academy Awards

In December last year, Sean Penn’s became vocal about the Academy’s failure to support The Apprentice, a film that critically chronicles Trump’s real estate days, a project which was denounced by the President.

According to the Daily Mail, Penn said at the 2024 Marrakech Film Festival,

“The Academy have exercised really extraordinary cowardice when it comes to being part of the bigger world of expression. And in fact, [they] have largely been part of limiting the imagination and very limiting of different cultural expressions.”

Continuing, Penn stated,

“Going back to The Apprentice, it’s jaw-dropping how afraid this business of mavericks is when they get a great film like that, with great, great acting.”

Although the Academy hadn't released its nominations at the time of Penn's comments, Daily Mail notes that it was largely anticipated that the film would not fare well at the Oscars.