SeanĀ Penn‘sĀ appearance on a new podcast has raised concerns that he may be facing a health challenge.
The 64-year-old actor seemed quite untidy, leading many social media users to note that he looked notably older than his actual age.
During the podcast, Sean Penn covered various topics such as his relationship with Madonna, President Donald Trump, and director Woody Allen, who faced allegations of abusing his adopted daughter.
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Sean Penn Looked ‘Unwell’ During A Podcast Appearance

During his recent appearance on a new podcast with Louis Theroux, Sean Penn triggered concerns about him due to his disheveled appearance.
Penn, the seasoned actor, sported a full head of grey hair that appeared messy and disheveled. Additionally, a visible gash on his nose attracted attention, as he had not made an effort to cover it with a bandage.
Further adding to his rugged look, Penn’s beard was particularly scruffy and in need of a trim.
Meanwhile, throughout the conversation with his host, Penn kept puffing cigarettes, which only added to the impression that he was not in the best shape physically.
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Netizens Express Worry Over The Actor For Looking ‘Unkempt’
Sean Penn in the house! Or rather, me in Sean Pennās 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
ā Louis Theroux (@louistheroux) May 13, 2025
In the comment section, fans pointed out that the 64-year-old was looking quite unwell for his age.
“I remember him for his father’s films of the 1970s. But Sean looks like he’s at war with himself,” a user commented on X.
“I’m his age. My 95-year-old father looks younger than him,” another individual remarked, while a third said, “Dude, seriously looks not well. Life has been rough on him, and he seems miserable.”
An X user noted, “Sean Penn opines on others’ lack of intelligence as he chain smokes cigarettes, unkempt and insufferable. Oh, Boy!!!”
Another said, “Sean Penn’s mind clearly matches his decrepit outward appearance.”
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Sean Penn Opened Up About His Failed Marriage To Madonna

Penn’s conversation with Theroux centered on a lot of interesting topics, including his four years of marriage to singer Madonna.
The two were married from 1985 until 1989 and remained cordial even after they finalized their divorce.
In her documentary, which was released two years after their split, Madonna called Penn the “love of her life.”
While Penn does remember the remarks she made about him and still feels grateful, he admitted that, looking back, they never should have gotten married in the first place.
“It didn’t take us long to realize that we had mistaken a good first date for a wedding partner,” Penn told his host.
He added, “It didn’t take us long to recover after we got divorced, maybe a year, in a friendship. I have a lot of fond memories of it ā it’s not all jail.”
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The Actor Says He Has No Issues Working With Woody Allen

Elsewhere during the chat, Penn weighed in on the allegations against Woody Allen, who was accused by his adopted daughter, Dylan Farrow, of sexual molestation.
“I don’t know anyone well enough to say, ā100 percent this didn’t happen, that didn’t happen,'” said Peen, per People Magazine. “The stories are mostly told by people that I wouldn’t trust with a dime. It just seems so heavily weighted in that way.”
Penn then pointed out that, despite the accusations and supporting claims from Dylan’s brother Ronan, Allen has yet to be proven guilty.
As such, he has no issues with working with the 89-year-old filmmaker, with whom he once worked in the 1999 musical comedy “Sweet and Lowdown.”
“I see he’s not proven guilty, so I take him as innocent, and I would work with him in a heartbeat.”
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Sean Penn Criticized President Donald Trump

At some point, the conversation was steered to President Donald Trump, whom Penn previously claimed “might try to destroy the world before he ages out of life.”
The actor noted that he had “briefly” met the president many years ago, and that the billionaire mogul isn’t “stupid,” contrary to what he believes is the “common conception” about him.
“I personally struggle with the idea that’s sufficient to explain what he is. He seems so smart.” Penn said, per Newsweek.
However, the seemingly positive remark was quickly followed by a series of criticisms, in which Penn explained why he called the president smart.
“Well, I think that people will look back and see that he was extremely smart for his time and what it valued. But what he values is so base,” Penn said. “I won’t equate that with intelligence. It’s truly void of soul. And reallyāthis is the other thingāit actively engages in cruelty often.”