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Sean Penn | Entertainment News, Photos, and Videos

Leonardo DiCaprio Shows Off His Rugged Good Looks on Set of New Mystery Project

Leonardo DiCaprio has started working on his mysterious new movie with Paul Thomas Anderson.

The 49-year-old Oscar winner was spotted on set of the project, which does not have an official title, on Thursday (February 1) in Los Angeles.

Dressed casually, Leonardo pulled his hair back and rocked some scruff on his face. He was photographed walking around set and exiting a car.

Keep reading to find out more…More Here! »

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Leonardo DiCaprio & Sean Penn To Star In 'Secret' & Expensive Paul Thomas Anderson Film With Regina Hall, Budget Revealed

Paul Thomas Anderson has assembled an all-star trio to star in his next film!

The Oscar-nominated director is set to helm an untitled film, which is looking to be his most expensive film to date, and he has cast longtime friends Leonardo DiCaprio and Sean Penn, as well as Regina Hall.

Keep reading to find out more…More Here! »

Sean Penn Photo Gallery

Sean Penn Reflects on Matthew Perry's Legacy

Sean Penn is opening up about the late Matthew Perry‘s impact on the world.

The 63-year-old Mystic River actor’s comments come roughly a month after the Friends star died at his Los Angeles home.

Sean notably crossed paths with Matthew when he appeared in two episodes of Friends in 2001.

Keep reading to find out more…More Here! »

Sean Penn & Girlfriend Olga Korotyayeva Spotted Getting Dinner with Rande Gerber in Malibu

Sean Penn and his girlfriend Olga Korotyayeva are enjoying some quality time with friends.

The 63-year-old Oscar-winning actor and the 43-year-old actress were seen having dinner with Casamigos co-founder Rande Gerber on Saturday night (September 16) at Nobu in Malibu, Calif.

The three stars were seen chatting outside of the restaurant following their meal before getting in the same car together and driving away.

Sean and Olga first sparked dating rumors in May when they were seen grabbing dinner together in Malibu. They’ve been spotted all over the world since then!

Make sure to check out highlights from Sean‘s new interview in which he reveals a surprising thing he did with his Oscar statues.

Browse through the gallery for 50+ photos of Sean Penn at dinner with his girlfriend and friend…

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Sean Penn Reveals What He Did With His Oscars, Reacts to Will Smith Slap & Hollywood Strikes

Sean Penn is getting candid about politics and the Oscars.

The 63-year-old star is on the cover of this week’s issue of Variety, out now.

During the conversation, Sean spoke about Ukraine, Will Smith, the SAG-AFTRA strike, Volodymyr Zelenskyy, Superpower and more.

Click through to find out what Sean Penn had to say…

Dakota Johnson & Sean Penn Attend Premiere of Their Cab Ride Movie 'Daddio' at TIFF 2023

Dakota Johnson and Sean Penn are bringing star power to the 2023 Toronto International Film Festival!

The two actors attended the premiere of their movie Daddio on Sunday (September 10) at the TIFF Bell Lightbox in Toronto, Canada.

Dakota, who also produced the movie, and Sean were joined by writer and director Christy Hall and producer Ro Donnelly.

Dakota “plays a woman who steps into a New York cab at the airport, driven by a man played by Sean. She’s clearly preoccupied and just wants to get home. He’s a curbside philosopher. Immediately, he engages her in conversation which starts in small talk then gets bigger, deeper, and riskier as he steers her to her destination.”

Christy told IndieWire about making a movie that is mostly contained to one location,“It does exist in Hollywood, character-driven chamber pieces, and we just decided unapologetically that we were going to boldly be one of them. Who doesn’t want to watch Sean Penn and Dakota Johnson up close and personal for 94 minutes?”

Dakota recently opened up about her close bond with another famous actress.

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Sean Penn & Girlfriend Olga Korotyayeva Hold Hands on Date Night at Giorgio Baldi

Sean Penn is enjoying a night out with girlfriend Olga Korotyayeva.

The 62-year-old two-time Oscar winner and the 43-year-old Ukrainian actress held hands as they left celeb hotspot Giorgio Baldi after a dinner date on Tuesday night (August 8) in Santa Monica, Calif.

PHOTOS: Check out the latest pics of Sean Penn

For their night out, Sean wore a navy jacket over a black T-shirt paired with jeans while Olga donned a navy dress.

Sean and Olga first sparked dating rumors in May when they were seen grabbing dinner together in Malibu.

Sean recently shared his support for the WGA strike, calling the dispute over AI a “human obscenity.” Find out everything else he said here.

Last month, Sean bumped into a famous friend during a day at the beach!

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