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Sean Penn Latest News, Photos, and Videos

Sean Penn Suits Up for a Day Out in New York City

Sean Penn makes a rare appearance while stepping out on Tuesday morning (August 22) in New York City.

The 57-year-old Oscar-winning actor was spotted looking handsome in a suit as he headed to an early morning business meeting.

PHOTOS: Check out the latest pics of Sean Penn

Later that day, Sean tried to ditch photographers as he was escorted by a few security guards as he felt his hotel.

Late last moth, Sean stepped out to support pal Leonardo DiCaprio at his foundation event in St. Tropez.

15+ pictures inside of Sean Penn out in NYC…

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Leonardo DiCaprio is Supported by Kate Winslet, Madonna, & More at His Foundation Gala

Leonardo DiCaprio is joined by tons of his famous friends as he hosts the 4th Annual Leonardo DiCaprio Foundation Gala on Wednesday (July 26) at Domaine Bertaud Belieu in St. Tropez, France.

The 42-year-old Oscar-winning actor was joined at the event by longtime friends Kate Winslet, Sean Penn, Tobey Maguire, and many more.

CHECK OUT: Leonardo DiCaprio, Kate Winslet, & Billy Zane Have a ‘Titanic’ Reunion at Charity Gala!

Leo and his foundation hosted the event to support protecting the earth and all of its inhabitants through projects that build climate resiliency, protect vulnerable wildlife from extinction, and restore balance to threatened ecosystems and communities.

During the event, Madonna and Lenny Kravitz took to the stage to perform for the guests.

FYI: Madonna is wearing Stephen Webster jewelry.

25+ pictures inside of the stars at the event…

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Sean Penn Photo Gallery

Leonardo DiCaprio Hangs Out Shirtless With Orlando Bloom, Tobey Maguire, & More at Fourth of July Party

Leonardo DiCaprio brought the heat this Fourth of July!

The 42-year-old actor was spotted partying shirtless at an oceanfront property on Wednesday (July 5) in Malibu, Calif.

PHOTOS: Check out the latest pics of Leonardo DiCaprio

He was joined by pals Orlando Bloom, Tobey Maguire, Kevin Connolly, Scott Eastwood, Adrien Brody, Sean Penn, and more.

Scott also stripped off his shirt while wearing a pink towel wrapped around his waist. Head to our gallery to see all the pics!

On Monday, Leo rocked an all-blue ensemble while attending another party at a beachside location in Malibu.

ICYMI, Leo, Orlando, and Tobey were also spotted spending some time in NYC together last month.

10+ pictures inside of Leonardo DiCaprio, Orlando Bloom, Tobey Maguire, and more at the party… More Here! »

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Sean Penn Reportedly Avoids Delta Airlines Confrontation

Sean Penn kept it cool during a recent airline experience!

According to E! News, the 56-year-old actor was on board a flight recently when two passengers tried to confront him.

Sean had reportedly placed his bags in an overhead compartment while seated in the economy class cabin but some other passengers wanted him to move them.

When the passengers got aggressive, thankfully members of the flight crew were nearby to diffuse the situation.

Thanks to Sean‘s calm attitude about the situation, he even got bumped to first class!

It looks like everything worked out for Sean!

Robin Wright & Sean Penn Land in NYC Together

It looks like Robin Wright and Sean Penn are still on good terms these days!

The 51-year-old actress and the 56-year-old actor were spotted arriving at JFK Airport together on Tuesday morning (May 30) in New York City.

Robin and Sean, who were married from 1996 to 2010, flew to the Big Apple together and got into the same car to leave the airport. See the photos and video now on TMZ.

It’s likely that the former couple are in town to visit their son Hopper, 23, who live in NYC.

The fifth season of Robin‘s series House of Cards was just added to Netflix today.

Robert De Niro Calls For Arts Program Funding at Chaplin Award Gala

Robert De Niro received a huge honor from the Film Society of Lincoln Center at the annual Chaplin Award Gala!

The 78-year-old two-time Academy Award-winner stepped out at the gala on Monday night (May 8) at the David H. Koch Theater at Lincoln Center in New York City.

Other attendees Michael Douglas, Ben Stiller, Martin Scorsese, Meryl Streep, and Sean Penn, who all presented throughout the evening.

During his acceptance speech, Robert called out “mean-spirited” Donald Trump for targeting arts programs.

“For their own divisive political purposes, the administration suggests that the money for these all-inclusive programs goes to rich liberal elites. This is what they now call an ‘alternative fact,’ but I call it bullshit,” he said during his speech.

Robert later added, “I don’t make movies for rich liberal elites…I make them for everybody.”

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Leonardo DiCaprio Supports Sean Penn at Haiti Takes Root Dinner

Leonardo DiCaprio takes a sip of wine while sitting with Sean Penn at the Haiti Takes Root benefit dinner on Friday night (May 5) at Sotheby’s in New York City.

The dinner was held to help the J/P Haitian Relief Organization’s mission to reforest and rebuild Haiti.

Some of the other celebs in attendance at the event included Ellie Goulding, Naomi Campbell, Andy Cohen, Gayle King, and Andra Day, who gave a performance during the dinner.

While Sean always hosts an event for his organization during Golden Globes weekend, this is his first event in NYC!

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