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Sean Penn, 64, sparks concern with VERY disheveled appearance at upscale celeb hotspot

Sean Penn had a disheveled appearance as he stepped out for dinner at the glitzy celebrity hotspot Nobu in Malibu this week. 

The Mystic River actor, 64 – who recently received a subtle dig from a fellow actor over his past Oscars win – was also joined by his eldest child Dylan, 33, for the lowkey outing. 

The star kept it casual wearing a pair of khaki trousers as well as a dark green jacket and white shirt underneath. 

Penn – who sported a scruffy beard and messy hair – additionally slipped into a pair of white sneakers to complete the ensemble for the nighttime excursion. 

After grabbing a bite to eat at the restaurant, Sean was seen stepping outside for a quick smoke break before being joined by his daughter. 

The actress was stylish in a sheer, black maxi skirt which was paired with a black leather jacket and comfy sneakers. 

Sean Penn, 64, sparks concern with VERY disheveled appearance at upscale celeb hotspot

Sean Penn, 64, had a disheveled appearance as he stepped out for dinner at the glitzy celebrity hotspot Nobu in Malibu this week

Her blonde locks were pulled back into a chic bun and she easily carried a black, Yves Saint Laurent purse over her shoulder.

The pair were later seen getting into the same vehicle with Dylan in the driver’s seat as they headed to their next destination. 

Penn shares his daughter as well as son Hopper, 31, with ex-wife Robin Wright – whom he was married to from 1996 through 2010. 

The actor also previously tied the knot with Madonna in 1985 but the former couple divorced in 1989. He was also married to Leila George from 2020 until 2022. 

Sean has most recently been romantically linked to Valeria Nicov, 30, and they made their red carpet debut late last year in November at the Marrakech International Film Festival. 

Dyan has followed in her parents’ acting footsteps, and has appeared in projects such as Night Hunter (2018), Flag Day (2021) and Signs Of Love (2022). 

Hopper is also an actor and is known for starring in films including Devil’s Peal (2023) and appeared with his sister Dylan and father Sean in Flag Day. 

It comes shortly after another Hollywood actor revealed that he had been shocked over his Oscars loss to Sean Penn. 

The star kept it casual wearing a pair of khaki trousers as well as a dark green jacket and white shirt underneath

The star kept it casual wearing a pair of khaki trousers as well as a dark green jacket and white shirt underneath

The pair were later seen getting into the same vehicle with Dylan in the driver's seat as they headed to their next destination

The pair were later seen getting into the same vehicle with Dylan in the driver’s seat as they headed to their next destination

Penn shares his daughter as well as son Hopper, 31, with ex-wife Robin Wright - whom he was married to from 1996 through 2010; Penn seen with Dylan and Hopper in Cannes in 2021

Penn shares his daughter as well as son Hopper, 31, with ex-wife Robin Wright – whom he was married to from 1996 through 2010; Penn seen with Dylan and Hopper in Cannes in 2021 

Bill Murray had been nominated for an Academy Award for Best Actor in 2004 for his role in Lost In Translation – but the win eventually went to Sean for his performance in Clint Eastwood’s Mystic River. 

Penn won again a few years later after starring in Gus Van Sant’s Harvey Milk biopic titled Milk. 

During an appearance on The Howard Stern Show late last month in March, the Groundhog Day star expressed: ‘It was sort of surprising.’ 

He added, ‘I won every other prize for Lost in Translation, so I just sort of thought I was gonna win, ’cause I’d won everything – every single one.’ 

While at first the actor had been disappointed about not scoring an Oscar, Bill told Stern that he now sees the loss as ‘kinda good.’

Murray stated, ‘I realize that I’d actually gotten sort of infected by wanting to win it. It attracted a low-grade virus of the desire for more. 

‘I had it for about six months; it had to wear off. So I did learn a lesson from it that if I’d won, I might not have ever seen.’ 

Sean has been keeping busy and has taken on a role in the upcoming film One Battle After Another – which is loosely based on the 1990 novel titled Vineland and written by Thomas Pynchon. 

Bill Murray had been nominated for an Academy Award for Best Actor in 2004 for his role in Lost In Translation - but the win eventually went to Sean for his performance in Clint Eastwood's Mystic River (seen above in 2004)

Bill Murray had been nominated for an Academy Award for Best Actor in 2004 for his role in Lost In Translation – but the win eventually went to Sean for his performance in Clint Eastwood’s Mystic River (seen above in 2004)

Paul Thomas Anderson not only directed the movie, but also wrote the script and produced the project. 

Alongside Penn – who plays Col. Steven J. Lockjaw in the film – other cast members include Leonardo DiCaprio, Teyana Taylor, Benicio Del Toro and Regina Hall. 

The premise is: ‘When their evil enemy resurfaces after 16 years, a group of ex-revolutionaries reunites to rescue one of their own’s daughter,’ per IMDB.   

One Battle After Another was made on a budget of around $140 million and is set to be released later this year on September 26, 2025. 

DiCaprio recently opened up about the movie earlier this month while at CinemaCon and also teased what viewers can expect, per The Hollywood Reporter. 

‘I’ve been wanting to work for Paul for over 20 years now. He’s one of the most unique talents of our time,’ the Titanic actor said. 

Sean has been keeping busy and has taken on a role in the upcoming film One Battle After Another - which is loosely based on the 1990 novel titled Vineland and written by Thomas Pynchon; seen in March in NYC

Sean has been keeping busy and has taken on a role in the upcoming film One Battle After Another – which is loosely based on the 1990 novel titled Vineland and written by Thomas Pynchon; seen in March in NYC 

Alongside Penn - who plays Col. Steven J. Lockjaw in the film - other cast members include Leonardo DiCaprio, Teyana Taylor, Benicio Del Toro and Regina Hall; Sean seen above in One Battle After Another

Alongside Penn – who plays Col. Steven J. Lockjaw in the film – other cast members include Leonardo DiCaprio, Teyana Taylor, Benicio Del Toro and Regina Hall; Sean seen above in One Battle After Another 

Anderson is known for other projects over the years such as The Master, There Will Be Blood, Phantom Thread and Licorice Pizza. 

Leonardo added, ‘With this film, he has tapped into something politically and culturally that is brimming beneath our psyche.’

The Oscar winner further explained that both he and other cast members were able to ‘improvise and become our own characters.’ 

DiCaprio then applauded the filmmaker and said his ‘ability to work with actors is so unique and bar none.’ 

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