Far-left Hollywood actor Sean Penn was publicly ridiculed this week for his unfiltered attacks on President Donald Trump and rough appearance.
During an episode of The Louis Theroux Podcast, Penn’s disheveled state turned heads almost as much as his anti-Trump commentary, with critics online wasting no time pointing out the irony of the actor’s attacks given his haggard look and violent history.
Appearing with a battered nose, wildly unkempt grey hair, and a face showing signs of wear well beyond his 64 years, Penn offered a series of critical takes on the president that quickly ignited backlash.
Asked by host Louis Theroux if he had ever met Trump, Penn admitted, “I have briefly, very briefly, many years ago,” adding that his first impression of the now-president was simply: “salesman.”
Sean Penn in the house! Or rather, me in Sean Penn’s house! The Hollywood acting legend and adventurer invited me up to his Malibu hideaway to talk Trump, Zelenskyy, Jack Nicholson, Madonna, punching photographers, jail time, smoking, and much more. It was a big thrill to do,… pic.twitter.com/VBGO0x68qx
— Louis Theroux (@louistheroux) May 13, 2025
Theroux pushed further, speculating on a broader misconception about Trump’s intellect.
“I sometimes wonder if people on the left underestimate him, and there’s this common conception that he’s stupid, right? Which is hard to buy,” Theroux said.
“I personally struggle with the idea that’s sufficient to explain what he is. He seems so smart.”
Sean Penn is only 64 years old❓
He doesn’t look a day over 85. pic.twitter.com/KtL6uslngk
— Dash Riprock 🇺🇸 (@PhilMcCrackin44) May 16, 2025
“Well, I think that people will look back and see that he was extremely smart for his time and what it valued,” the actor conceded, before pivoting to moral judgment.
“But what he values is so base. I won’t equate that with intelligence. It’s truly void of soul. And really—this is the other thing—it actively engages in cruelty often.”
The Oscar-winner went on to claim that current events, including the involvement of tech mogul Elon Musk, support his claim that Trump’s motivations are rooted in destruction.
“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,” Penn said.
“And so, I can’t associate that with any intelligence that’s going to do humankind any good.”
When Theroux asked what Trump values, Penn replied, “His own instrument reward system.” That prompted the host to inquire, “To reward what? His ego and vanity?”
“Yeah. The tough guy who never was,” Penn answered. “He was his father’s punk from Queens for a long time. You know, the tall Q-tip guy in school. He got into business. He got around a lot of real tough guys. Gangsters.”
Sean Penn is only 64 years old. TDS has ravaged him.
Here he talks about his issues with paparazzi and wanting to end their lives.
Penn is not well. pic.twitter.com/LpwPdpZ8n0
— Paul A. Szypula 🇺🇸 (@Bubblebathgirl) May 15, 2025
“Dodged conscription. Cadet Bone Spurs,” Theroux added in reference to Trump’s medical diagnosis during the Vietnam War.
“He found that he didn’t have any of the complications of what I think you or I would associate with morality that would allow him to ride side saddle with real tough guys,” he went on. “That’s what it seems like.”
Keyboard warriors were quick to call out what they saw as the actor’s hypocrisy and overall irrelevance. The focus for many turned to Penn’s appearance, which some said undermined his credibility.
“Dude who hospitalized his wife and sued anyone that tried exposing it thinks Trump is a bad guy. Fascinating,” one commenter remarked about Penn’s violent history.
“Sean Penn, a Man so drugged out and lived a life of degeneracy for over 3 decades has an opinion… still grasping for some kind of resemblance and relevance in a cult of deprivation,” another wrote.
One user joked, “Dang he aged like a worn leather handbag,” while another claimed, “I’m his age. My 95-year-old father looks younger than him.”
“Dude seriously looks not well. Life has been rough on him and he seems miserable,” someone else said bluntly.
“I can’t listen to people who have advanced TDS,” another commented, referring to Trump Derangement Syndrome.
This isn’t the first time this month that the poorly aging actor has made hysterical claims about Trump.
In a recent appearance on The Jim Acosta Show, he compared Trump to a violent, vengeful spouse.
Asked whether Trump might refuse to leave office at the end of a second term, Penn painted a dark hypothetical.
NEW: Actor Sean Penn says President Trump is like a “spouse-murd*rer,” floats a “worst-case scenario” where Trump destroys the world.
This guy looks horrible.
The comment came as Penn was discussing with Jim Acosta and Eric Swalwell about what the rest of Trump’s presidency… pic.twitter.com/Q2cOUhtnPR
— Collin Rugg (@CollinRugg) May 4, 2025
“We should consider worst-case scenarios,” he said, theorizing that Trump “might try to destroy the world before he ages out of life.”
“I do think it’s a reasonable theory that Donald Trump is not unlike the spouse of someone who leaves him, perhaps for another, who then murders their former partner because if they can’t have her, nobody can,” he added.
“I think Donald Trump and his solipsism may have that relationship with the world and that this destruction is in part a power play, and also a literal intention of his final out,” Penn rambled on.
The podcast also featured Democratic Congressman Eric Swalwell, who collaborated with Penn on the project he’s been touting, “Words of War.”
Swalwell voiced concern that Trump could take drastic actions if he feels politically cornered.
“What worries me is if he doesn’t believe there’s somebody who can protect him, you will see him ratchet up what he’s willing to do to the country to protect himself,” he said.
“Our only hope is a Congress that will check it, a press that will report on it, a court that’s independent to rule on it and a town square filled with Americans who say ‘hell no,’” he concluded.
Watch the full interview here: