Sean Penn: From Hollywood Playboy To A Happy Husband

Sean Penn is a remarkably talented actor. He's starred in great roles that have earned him multiple awards in Hollywood. Besides his acting chops, we've also been intrigued by his highly publicized private life. The star has had some great love stories from Madonna to Charlize Theron. Join us as we dig into his epic romances and heartbreaks.

Sean Penn/Photo:Getty Images

Sean Penn/Photo:Getty Images


LATEST NEWS

During August 2020, 60-year-old Penn shared with Seth Meyers that he and his 28-year-old fiance Leila George recently got married. “We did a COVID wedding,” the actor explained. “By that I mean it was a county commissioner on Zoom, we were at the house, my two children and her brother, and we did it that way.” The couple has been dating since 2016. 

Sean Penn and Leila George/Photo:Getty Images

Sean Penn and Leila George/Photo:Getty Images


But it hasn't always been smooth sailing, the couple has experienced some rough patches. A close source told People they have been on and off for a while, "They got together and then they broke up, and Sean won her back," says the source. "He realized he had made a mistake and when he felt he might lose her, he worked hard to get her back."


The couple reunited during the lockdown and bonded again through getting involved with various humanitarian relief efforts. It's a great thing that their love is reignited by helping other people.

Sean Penn and Leila George/Photo:Getty Images

Sean Penn and Leila George/Photo:Getty Images


THE OTHER WOMEN

The young Sean Penn and the Downton Abbey star locked eyes on the set 1984 flick Racing with the Moon. He was 24 and she was 23; they soon fell deeply in love and just like any other beautiful love story, the two got engaged. Except there was no happily-ever-after.

Sean Penn holds Elizabeth McGovern in publicity portrait for the film 'Racing With The Moon', 1984. (Photo by Paramount/Getty Images)

Sean Penn holds Elizabeth McGovern in publicity portrait for the film 'Racing With The Moon', 1984. (Photo by Paramount/Getty Images)


The two went their separate ways when McGovern decided that she wanted to pursue her theater career in New York. In recent years, she's described their relationship as 'exhausting.' When asked if she regrets her decision, the actress said, “No. You’d go mad if you did."


During their engagement, Elizabeth felt torn about her decision and she wondered if they would have eventually walked down the aisle. But from the way she's talked about their relationship in the past, the two had a tumultuous romance. The star used words such as "dramatic" to paint the picture. 


TWO HOLLYWOOD GREATS HOOK UP

Susan Sarandon and Sean have appeared alongside each other films but the on-screen chemistry did spill over into real life for a brief moment. Rumor has it that the two became romantically involved during the mid-1980s. Why not? When they were two of the hottest talents in Hollywood.

Susan Sarandon/Photo:Getty Images

Susan Sarandon/Photo:Getty Images


Unfortunately, it just wasn't meant to last but that doesn't mean the two weren't able to remain friends after their entanglement. In 1995, the former lovers acted in Dead Man Walking together. The two even took part in a humanitarian visit to Haiti together in 2010.

 Sean Penn greets Susan Sarandon after a visit to a camp for internally displaced persons managed by Penn and his Jenkins-Penn Humanitarian Relief Organization in Port-Au Prince, Haiti. The group, Artists for Peace and Justice is working to rebuild Haiti�s education system on April 12, 2010 in Port-au-Prince, Haiti. (Photo by Kevork Djansezian/Getty Images for Artists For Peace And Justice)

Sean Penn greets Susan Sarandon after a visit to a camp for internally displaced persons managed by Penn and his Jenkins-Penn Humanitarian Relief Organization in Port-Au Prince, Haiti. The group, Artists for Peace and Justice is working to rebuild Haiti�s education system on April 12, 2010 in Port-au-Prince, Haiti. (Photo by Kevork Djansezian/Getty Images for Artists For Peace And Justice)


MARRIED TO MADONNA 

Sean and Madonna were probably one of the most prolific couples of the 1980s. The stars met in 1984 in a studio parking lot while the singer was filming her music video for Like A Virgin. 6 months after their initial meeting, the couple got hitched, and the media became obsessed with the duo.

Madonna and Sean Penn leave rehearsals for their play 'Goose and Tom Tom' in August 1986 in New York City, New York. (Photo by Vinnie Zuffante/Michael Ochs Archives/Getty Images)

Madonna and Sean Penn leave rehearsals for their play 'Goose and Tom Tom' in August 1986 in New York City, New York. (Photo by Vinnie Zuffante/Michael Ochs Archives/Getty Images)


But, there was a dark cloud over their heated romance. While the pair filmed their movie Shanghai Surprise, Penn became jealous of Madonna's male friends. Their relationship went downhill and it ended in divorce after 4 years of marriage.

Madonna/Photo:Getty Images

Madonna/Photo:Getty Images


In 1991, Madge referred to the Oscar-winning actor as the love of her life. Despite their split, the two have remained good friends and they never shut down a photo opportunity during a night out in Hollywood. In a 2018 interview, Penn revealed that he still has a special place in his heart for the hitmaker.

Sean Penn/Photo:Getty Images

Sean Penn/Photo:Getty Images


"Ah, I love my first wife very much," the actor shared after being asked who he prefers between Britney Spears and Madonna. It looks as though the love is still real between the both of them as in 2016, the pop sensation admitted to still being in love with Penn. 

BEVERLY HILLS, CA - JANUARY 09: (L-R) David Banda, Mercy James, musician Madonna, and actor Sean Penn arrive at the 5th Annual Sean Penn & Friends HELP HAITI HOME Gala benefiting J/P Haitian Relief Organization at Montage Hotel on January 9, 2016 in Beverly Hills, California. (Photo by Matt Winkelmeyer/Getty Images)

BEVERLY HILLS, CA - JANUARY 09: (L-R) David Banda, Mercy James, musician Madonna, and actor Sean Penn arrive at the 5th Annual Sean Penn & Friends HELP HAITI HOME Gala benefiting J/P Haitian Relief Organization at Montage Hotel on January 9, 2016 in Beverly Hills, California. (Photo by Matt Winkelmeyer/Getty Images)


She offered to marry him again if he contributed $150 000 to her charity. Speaking at a fundraising event, Madonna said, "I want to say, Sean, that I love you from the moment that I laid eyes on you and I still love you just the same. I just wish you'd stop smoking so many cigarettes." After over 30 years, the flame is still alive. 

Madonna/Photo:Getty Images

Madonna/Photo:Getty Images


MARRIAGE WITH ROBIN WRIGHT 

After the flaming hot relationship with the world's biggest pop star, Penn became serious with the actress Robin Wright. The couple dated for 5 years and even though they experienced some ups and downs, they decided to get married in 1996.

Sean Penn and Robin Wright/Photo:Getty Images

Sean Penn and Robin Wright/Photo:Getty Images


In 2007, the couple called their marriage off but they soon rekindled their love until they could no longer keep their spark alive. The actors share two children Dylan, 28, and Hopper, 26. In fact, raising their children has been the most difficult challenge of their post-divorce relationship. 

"Divorce in and of itself, and with children, is devastating," Wright once revealed.

Dylan and Hopper Penn/Photo:Getty Images

Dylan and Hopper Penn/Photo:Getty Images


The House of Cards star also shared why they were on and off. "One of the reasons why we got back together and broke up so much was trying to keep the family together. If you’ve got kids, it’s a family, and you try again, and you try again. We did that for a long time."

Robin Wright/Photo:Getty Images

Robin Wright/Photo:Getty Images


Speaking about his co-parenting relationship with Wright, Penn revealed that they barely communicate. He also added that their relationships with their kids are different, "As it turned out she and I did not share the same ethical views on parenting, including the continuing parenting of adult children.”

Robin Wright/Photo:Getty Images

Robin Wright/Photo:Getty Images


SEAN AND CHARLIZE 

Sean had known the South African star for years before they started dating in 2013. Charlize shared that they had been friends for 20 years. In 2004, they celebrated winning their Oscar's on the same evening. It's only natural that their relationship grew from strength to strength.

Charlize Theron and Sean Penn/Photo:Getty Images

Charlize Theron and Sean Penn/Photo:Getty Images


“I think our friendship stemmed from mutual respect — more on my end because I really didn't have a body of work twenty years ago, but my love and passion for making films — that was our common ground,” Theron explained

Sean Penn and Charlize Theron/Photo:Getty Images

Sean Penn and Charlize Theron/Photo:Getty Images


Their official romance was confirmed in 2014. It wasn't long before the engagement rumors started swirling but it seems the two preferred to take their time and live out their lives. The pair even embraced each other's children. Charlize is a mom to two adopted kids. 

Charlize Theron/Photo:Getty Images

Charlize Theron/Photo:Getty Images


A year after they split, Theron shared that Sean understood that she was a mom first. "There was an understanding that I was a single mom with a very young boy who I had to put in a situation where he understood that Mommy dates, but that he does not have a father." The couple broke up just before the actress adopted her second child.

Charlize Theron and her adopted child /Photo:Getty Images

Charlize Theron and her adopted child /Photo:Getty Images


But, they did have an agreement about her new addition. “We had a very clear understanding. He knew that I was thinking about filing for another adoption, but that we weren't filing together," Theron shared. The actress had also won over Sean's kids. “She's the only woman since my mom, who can shut my dad up. The only woman!" said his daughter Dylan.


Their breakup was surrounded by speculation but they simply grew apart. Rumor has it Charlize ghosted Sean. But she begs to differ, "There is a need to sensationalize things. When you leave a relationship there has to be some f—ing crazy story or some crazy drama. And the f—ing ghosting thing, like literally, I still don't even know what it is. It's just its own beast."

Sean Penn/Photo:Getty Images

Sean Penn/Photo:Getty Images


ON TO THE NEXT ONE: SCARLETT JOHANSSON 

The Hollywood elites were spotted going on a few dates together, holding hands and looking flirty. However, their romance didn't last very long. The pair called it quits after two months. Apparently, Scarlett was more interested in getting serious than Sean. Oh well, they both moved on to greater love so not all is lost. 

Scarlett Johansson/Photo:Getty Images

Scarlett Johansson/Photo:Getty Images


RUMORED RELATIONSHIPS 

In 1996, Penn and Elle Macpherson were spotted looking comfortable together and it led to rumors of them dating. He's also been linked to the gorgeous Natalie Portman. However, they both denied that they were ever romantically involved and we've heard nothing about them since.

Natalie Portman/Photo:Getty Images

Natalie Portman/Photo:Getty Images


In 2015, the Pieces Of You singer Jewel Kilcher shared that she had a secret relationship with Sean. Jewel revealed that she caught Penn's eye when she had a first-time appearance on Conan O'Brien's show in 1995. He was quite persistent and charming according to the performer.

 Jewel performs onstage at the Nashville Songwriters Awards 2018 at Ryman Auditorium on September 19, 2018 in Nashville, Tennessee. (Photo by Jason Kempin/Getty Images)

Jewel performs onstage at the Nashville Songwriters Awards 2018 at Ryman Auditorium on September 19, 2018 in Nashville, Tennessee. (Photo by Jason Kempin/Getty Images)


However, their relationship could never be public because she was in a relationship with another public figure. Not long after the actor's split from Theron, he was spotted with another actress Minka Kelly. The two had been seen out together on multiple occasions during 2015 and 2016. But, Kelly denied any flirty fling between them,

Minka Kelly/Photo:Getty Images

Minka Kelly/Photo:Getty Images


However, it's clear that they had a good friendship. Reports also revealed that he had a short encounter with the Mexican actress Kate del Castillo while on a mission to meet the infamous fugitive Joaquin ‘El Chapo’ Guzman. del Castillo revealed that she and Sean became acquainted in 2016. 

Kate del Castillo/Photo:Getty Images

Kate del Castillo/Photo:Getty Images


They agreed to join forces in locating and meeting the crime lord to discuss a possible documentary about his life. However, they spent a steamy night together, “I never felt for him (Penn),” she told Good Morning America. “We had sex. We are both adults, single, and something was going on, but that was it. It was business.” 

Kate del Castillo/Photo:Getty Images

Kate del Castillo/Photo:Getty Images


After the capture of El Chapo, Sean wrote a 10 000 word piece for Rolling Stone about the meeting the controversial figure. That's when the Latina actress and Penn fell out because he reportedly didn't inform her that he would write an article with false claims according to the actress.

Kate del Castillo/Photo:Getty Images

Kate del Castillo/Photo:Getty Images


WHAT DO WE KNOW ABOUT HIS KIDS?

Sean's daughter Dylan and son Hopper mean the world to him and he's a proud father. “They’re amazing people. They’re both acting and modeling, an industry that I’m not very interested in but they seem to have fun with it,” he says. “I’m supportive of whatever my kids do that keeps them happy and healthy, period,” the 60-year-old shared.

Sean Penn/Photo:Getty Images

Sean Penn/Photo:Getty Images


His daughter is incredibly hardworking, she's appeared in magazines such as Elle and GQ. You might have seen her on Nick Jonas' Chains music video. Dylan has appeared in films like Condemned and Elvis & Nixon; you can bet there is more coming in the pipeline too.


Like Penn explained, Hopper is keen on acting too. You may have noticed him in the films like The Last Face, War Machine, and Between Worlds, opposite Nicolas Cage. Sean Penn is set to director his one and only son in the upcoming movie Flag Day.

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