

Longtime Hollywood actor and director Sean Penn drew concern from fans this week after he was spotted looking noticeably disheveled during a rare public appearance at the upscale Nobu restaurant in Malibu, California. The 64-year-old Oscar winner was photographed outside the high-end eatery on a smoke break, dressed casually in what many described as a rumpled and stained outfit.
Wearing a wrinkled olive green jacket over a white T-shirt paired with khaki pants, Penn appeared tired and unshaven, with scruffy facial hair and tousled hair adding to the overall look of fatigue. His appearance quickly sparked reactions on social media, with some fans expressing concern about his well-being.
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He wasn’t alone, however. Penn was accompanied by his daughter, Dylan Penn, who contrasted her father’s low-key look with a more styled appearance.
She wore a leather jacket, a sheer maxi skirt, and classic Vans sneakers. The two were later seen leaving the restaurant together, with Dylan behind the wheel of the car.
A complicated past and shifting public image
This isn’t the first time Penn’s appearance has stirred discussion. Throughout his decades-long career, the actor has often presented a rugged, unconventional public image that reflects his outspoken nature and intensity as both an artist and activist.
However, the most recent photos have added to growing speculation about his personal life and health.
Penn is known for keeping his private life relatively guarded, though he has been married three times-to Madonna (1985-1989), Robin Wright (1996-2010), with whom he shares both Dylan and Hopper Jack, and more recently, Leila George (2020-2022). While his relationships have often made headlines, he’s recently kept a lower profile in terms of romantic life, instead appearing publicly with his children or attending film-related events.
The Oscar winner has also made waves with his bold commentary on the entertainment industry. In December 2024, Penn publicly criticized the Academy Awards, accusing the organization of demonstrating “extraordinary cowardice” and failing to support diverse and daring storytelling in film.
This criticism came amid a broader cultural debate about the future of filmmaking, with Penn championing directors and projects that challenge the status quo.
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