Disheveled Sean Penn puffs on cigarette during dinner with daughter at swanky LA hotspot

Sean Penn appeared very disheveled while taking a smoke break at a swanky celebrity hotspot in Los Angeles.

The Oscar-winning star puffed on a cigarette before being joined by his daughter, Dylan Penn, outside Nobu restaurant in Malibu, Calif.

The actor had a scruffy beard and unkempt hair for the nighttime outing.

A disheveled Sean Penn was photographed smoking outside of Nobu in Malibu, Calif., Wednesday. BACKGRID
A disheveled Sean Penn was photographed smoking outside of Nobu in Malibu, Calif., Wednesday. BACKGRID
The “Mystic River” star was joined by his daughter, Dylan Penn. BACKGRID
The “Mystic River” star was joined by his daughter, Dylan Penn. BACKGRID

Sean, 64, sported an olive green jacket, white T-shirt and khaki pants that appeared to be stained.

Meanwhile, Dylan, 33, was more dressed up in a leather jacket, sheer maxi skirt and Vans.

The father-daughter duo was later seen driving away with the “Milk” star in the passenger seat.

The two later drove off together. BACKGRID
The two later drove off together. BACKGRID
Sean is also the father of son Hopper Jack Penn. Michael Kovac
Sean is also the father of son Hopper Jack Penn. Michael Kovac

Sean shares his daughter and son Hopper Jack Penn, 31, with his ex-wife Robin Wright.

The ex-spouses were married from 1996 to 2010. Sean was also previously married to Madonna from 1985 to 1989 and Leila George from 2020 to 2022.

The “Dead Man Walking” star was most recently romantically linked to actress Valeria Nicov when they were seen packing on the PDA in Madrid in September 2024.

The following month, the couple made their red carpet debut at the Marrakech International Film Festival in Morocco.

He shares his two kids with ex-wife Robin Wright. WireImage
He shares his two kids with ex-wife Robin Wright. WireImage
They were married from 1996 to 2010. AP

Sean also made headlines in December when he went on an anti-Oscars rant while smoking at a press conference.

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

“So I don’t … get very excited about what we’ll call the Academy Awards [except for] when a film like ‘The Florida Project’ or ‘I’m Still Here’ or, you know, ‘Emilia Perez,’ of the things that are likely to happen this year.”

In December 2024, Sean made headlines for smoking while critiquing the Oscars during a press conference. REUTERS
In December 2024, Sean made headlines for smoking while critiquing the Oscars during a press conference. REUTERS
He also praised the 2024 biopic “The Apprentice” about President Trump. WireImage
He also praised the 2024 biopic “The Apprentice” about President Trump. WireImage

Sean then praised the controversial biopic “The Apprentice” starring Sebastian Stan as President Trump.

“When something sneaks through, it’s to be celebrated,” he added. “It’s jaw-dropping how afraid this [so-called] business of mavericks is of a great film like that.”

The actor has been an outspoken critic of Trump.