Disheveled: Sean Penn Spotted Smoking Outside LA Hotspot During Dinner With Daughter Dylan

The Oscar-winner stepped out for a low-key night at Nobu Malibu with daughter Dylan Penn, sparking headlines for his rugged appearance and signature cigarette break.

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April 12, 2025: Sean Penn, 64, turned heads once again—this time not for his political views, but for his scruffy, off-duty look. The two-time Oscar winner was seen taking a smoke break outside the celeb-favorite Nobu restaurant in Malibu on Wednesday night. Dressed casually in a stained olive jacket, T-shirt, and khakis, Penn’s disheveled style raised eyebrows as paparazzi snapped him mid-puff.

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He wasn’t alone. The “Mystic River” star was joined by his daughter Dylan Penn, 33, who opted for a chic leather jacket and sheer maxi skirt paired with Vans. The father-daughter duo later drove off together, offering a rare public glimpse into their close bond.

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A Glimpse into the Private Life of a Hollywood Maverick

Sean Penn shares Dylan and son Hopper Jack Penn, 31, with ex-wife Robin Wright, whom he was married to from 1996 to 2010. The actor’s romantic history includes previous marriages to Madonna and Leila George, and most recently, a red carpet appearance with actress Valeria Nicov in late 2024.

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Despite his laid-back demeanor during family dinners, Penn continues to be a polarizing public figure. In December, he delivered a fiery critique of the Academy Awards while smoking during a press conference, calling the Oscars “cowardly” and praising bold cinema like The Florida Project and The Apprentice—a 2024 biopic on Donald Trump.

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Love Him or Hate Him, Penn Remains Unfiltered

Known for speaking his mind and staying true to his convictions, Sean Penn remains one of Hollywood’s most outspoken figures. Whether at political summits, red carpets, or late-night dinners with family, he stays unapologetically himself—beard, cigarette, and all.

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Tags: Sean Penn, Dylan Penn, celebrity sightings, Nobu Malibu, Sean Penn daughter, Sean Penn smoking, Robin Wright, Sean Penn Valeria Nicov, Sean Penn Oscars rant, celebrity families, Hollywood nightlife