Two-time Academy Award winner Sean Penn is one of the most revered actors of his generation. However, in his early years the star was more renowned for his turbulent private life than his talents. That’s perhaps unsurprising due to the fact he was once married to the undisputed Queen of Pop: Madonna.
Yes, back in the mid-1980s, Penn and Madonna were Hollywood’s hottest young power couple. The pair first met in February 1985 and just six months later, on the pop star’s birthday, they walked down the aisle together. And within a year they had made their personal relationship a professional one, too.
The then-happy couple appeared on screen together in 1986’s critically panned comedy adventure Shanghai Surprise. Madonna also later paid tribute to Penn on her third studio LP True Blue, describing him as “the coolest guy in the universe.” But the honeymoon period soon ended – and in dramatic fashion as well.
In 1987 Penn received a 60-day jail sentence for attacking a photographer during a movie shoot. Shortly after, Madonna decided she wanted out and issued him with divorce papers. The pair briefly managed to patch up their differences. But in 1989, in charges which were later dropped, the pop icon allegedly claimed that Penn had beaten her up at their Malibu home and the pair split for good.
Of course, Madonna wasn’t Penn’s first high-profile celebrity partner – nor the last. The actor had previously been engaged to Elizabeth McGovern, who he had starred alongside in the 1984 drama Racing with the Moon. And following his divorce from Madonna, he entered into a relationship with another actress, Robin Wright.
Penn and Wright had two children together, Dylan Francis in 1991 and Hopper Jack two years later. They went their separate ways in 1995, with Penn going on to forge a relationship with singer-songwriter Jewel Kilcher. However, a year later he reunited with Wright and the pair went on to marry in the Californian town of Ross.
But in 2007 Penn once again found himself in a precarious marital situation. He and his wife, now called Wright Penn, initially looked to be heading for the divorce courts before they asked for their case to be dismissed. Two years later the actor filed and then withdrew a case for legal separation. Then it was Wright Penn’s turn to issue the papers, and the couple officially and finally divorced in 2010.
Three years later, Penn began stepping out with a fellow Oscar winner, Charlize Theron. The A-list pairing confirmed their engagement at the end of 2014. But within six months the couple had called it off and gone their separate ways. However, the pair still went on to work together, with Theron taking the leading lady role in the Penn-directed drama The Last Face.
Penn’s own acting career began in 1974 with an extra role on Little House on the Prairie, the family drama his father Leo directed many episodes of. During his early years Penn also made various shorts with friends who would also go on to crack Hollywood, Charlie Sheen and Emilio Estevez. Penn’s brother, Chris, who sadly died in 2006, also enjoyed success as an actor.
In a 2009 Rolling Stone interview, Penn revealed he experienced a childhood of contrasts, commenting, “I’d say it was a combination of Huck Finn and Rumble Fish. There was a culture of what I’d call soft violence, in the sense that we didn’t let outside surfers surf our beach. We were vandals, we brought wrist-rockets to the beach, beat people up. Some people are kind of shocked by this but ten of the guys I grew up with are dead.”
Penn first caught attention with the role of a military cadet in 1981’s Taps. He then stole the show as stoner surfer dude Jeff Spicoli in teen classic Fast Times at Ridgemont High a year later. And in 1983 he impressed in a more serious role: delinquent Mick O’Brien in Bad Boys.
In 1985 Penn portrayed Andrew Daulton Lee, a real life ex-drug dealer given a life sentence for espionage, in The Falcon and the Snowman. Remarkably, on his release 13 years later, Lee was offered a job as the actors’s assistant. But returning to the 1980s, Penn ended the decade with key roles in Judgement in Berlin, Casualties of War and We’re No Angels.
Penn picked up his first Golden Globe nod for his supporting turn as David Kleinfeld in 1993’s Carlito’s Way. And the accolades continued two years later with his powerful Oscar-nominated performance as a death row inmate in Dead Man Walking. Then in 1999 he was recognized by the Academy again for his role in Woody Allen film Sweet and Lowdown.
And Penn’s golden streak continued well into the new century. He received a third Oscar nod for his portrayal of a mentally challenged dad in 2001’s I Am Sam. And he finally got the chance to make an acceptance speech when he was crowned Best Actor for his performance as James ‘Jimmy’ Markum in neo-noir Mystic River.
Penn also impressed with his portrayal of failed assassin Samuel Byck in 2004’s The Assassination of Richard Nixon. And although 2006’s critical and commercial All the King’s Men flopped hard, he soon bounced back with 2008’s Milk. This saw Penn pick up his second Academy Award for his measured performance as politician and gay rights activist Harvey Milk.
In 2010 Penn starred in the adaptation of ex-CIA officer Valerie Plume’s autobiography, Fair Game. A year later he appeared in the Palme d’Or winning drama The Tree of Life and in 2015 he showcased his action hero skills in The Gunman. In 2019 Penn portrayed another real-life figure, U.S. army surgeon William Chester Minor in The Professor and the Madman.
Of course, Penn’s talents extend beyond acting. The star is just as accomplished behind the scenes, having made his directorial debut on 1991’s The Indian Runner. He later helmed 1995’s The Crossing Guard, The Pledge six years later and 2007’s Into the Wild. Penn has also directed music promos for Peter Gabriel, Shania Twain and Lyle Lovett.
Unfortunately, Penn didn’t fare too well with his 2016 directorial effort, The Last Face. In fact, audiences booed the drama on its screening at the Cannes Film Festival. And the press was just as brutal, with The Hollywood Reporter describing it as a “stunningly self-important but numbingly empty cocktail of romance and insulting refugee porn.”
Perhaps burned by the hostile response to The Last Face, Penn announced in 2018 that he was no longer interested in filmmaking. Instead he claimed that his creative energies would be dominated by writing for the “foreseeable future.” That year he published his first book, Bob Honey Who Just Do Stuff.
Penn has also been involved in various charity and philanthropy endeavors over the years. In 2005 he helped to rescue people caught up in the devastating Hurricane Katrina in New Orleans. Five years later he set up a relief organization to aid those affected by the Haiti earthquake. And in 2010 he lent his support to various flooded villages in Pakistan.
As you’d expect from such an outspoken star, Penn hasn’t been afraid to voice his political opinions, either. In 2010 he argued that anyone describing his friend Hugo Chavez, the president of Venezuela, as a dictator should be arrested. Following Chavez’s death three years later, Penn said, according to CNN, “Today the United States lost a friend it never knew it had. And poor people around the world lost a champion.”
In 2012 Penn caused controversy when he appeared to offer his support to Argentina in the dispute over the Falkland Islands with the United Kingdom. Simon Weston, a veteran of the 1982 Falklands War, subsequently blasted the actor. He told the BBC, “Sean Penn does not know what he is talking about and, frankly, he should shut up. His views are irrelevant and it only serves to fuel the fire of the Argentinians and get them more pumped up.”
Penn’s eventful life story took another bizarre twist in 2016 when it was revealed he’d conducted an interview with notorious drug lord El Chapo. Alongside actress Kate del Castillo, Penn had spoken to the Mexican criminal just before he’d been captured. The White House described the meeting as “maddening,” while the Attorney General of Mexico also launched an investigation into it.
In 2002 he wrote an open letter to George W. Bush imploring him to reconsider his plans to attack Iraq. The plea, for its part, was published in the Washington Post at a cost of $56,000. And later that same year, he actually traveled to the Middle East nation in protest of the military strike planned by the Bush administration.
Penn was supported in this particular endeavour by a seemingly unlikely ally, his first ex-wife. Referring to the actor’s comments about Bush, Madonna told Q magazine, “Sean is one of the few. Good for him. Most celebrities are keeping their heads down. Nobody wants to be unpopular. But then Americans, by and large, are pretty ignorant of what’s going on in the world.”
And this wasn’t the last time that Madonna would leap to her ex-husband’s defence, either. In 2015 she refuted the age-old rumors that Penn had physically assaulted her during their four-year marriage. The singer signed an affidavit from the actor’s lawyers in which she stated that the reports were “completely outrageous, malicious, reckless, and false.”
Madonna had made the comments in court documents following a lawsuit worth $10 million which Penn filed against Lee Daniels. The co-creator of Empire had referred to the allegations about Penn and spousal abuse during a chat with The Hollywood Reporter. Madonna also added, “While we certainly had more than one heated argument during our marriage, Sean has never struck me, ‘tied me up,’ or physically assaulted me.”
A year later, Madonna and Penn appeared to prove that they’d truly patched up any differences once and for all at a charity fundraiser organized by the Queen of Pop. Staged in aid of her Raising Malawi initiative, the event saw Penn bid for a dress covered in Swarovski crystals. During the auction, Madonna told Penn, “I’m still in love with you.” She also joked she’d wed him again as long as he paid $150,000 for the item.
In fact, Penn did much better than that; he paid $160,000 for the extravagant dress, much to Madonna’s delight. He later joined his ex-wife on stage while photos of their 1985 nuptials were being put up for auction. After using a pair of handcuffs to restrain her, Madonna joked, “For once, he’s not the one being arrested.”
Later that same year Madonna once again made it apparent that she still has strong feelings for her first ex-husband. At another charity gala, the singer said, “I want to say, Sean, that I [loved] 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.”
Perhaps inevitably, speculation that the pair were actually in the process of getting back together continued to grow. In fact, Page Six even quoted an unnamed source who claimed that “everyone knows that Sean Penn is back with Madonna.” However, these rumors so far appear to have been completely unfounded.
However, Penn did continue the love-in two years later during an appearance on The Late Show with Stephen Colbert. In a bit titled “Sean Penn-y For Your Thoughts,” the actor was asked by the host who his favorite was out of Britney Spears and Madonna. Penn replied, “Ah, I love my first wife very much.”
“There’s no [comparison]… you don’t compare those things,” Penn added to further clarify his obvious answer. Colbert then explained why he’d asked the question in the first place, saying, “People compare them all the time! So you’re going to go with Madonna?” A smiling Penn then simply responded, “Sure!”
Despite his divorces from Madonna and Robin Wright and failed relationships with Elizabeth McGovern, Jewel Kilcher and Charlize Theron, Penn admitted he’s still open to the idea of romance. He told Colbert, “I’m never going to take a position that I’m closed off to love. People falling in love with each other is a great, great thing.”
Penn’s Madonna comments were in stark contrast to those he made during an interview with Esquire in 2012. He said, “There is no shame in saying that we all want to be loved by someone. As I look back over my life in romance, I don’t feel I’ve ever had that. I have been the only one that was unaware of the fraud in a few of these circumstances blindly.”
Sticking the knife in even further, Penn added, “When you get divorced, all the truths come out, you sit there and go, ‘What the f*** was I doing? What was I doing believing that this person was invested in this way?’ Which is a fantastically strong humiliation in the best sense. It can make somebody very bitter and very hard and closed off, but I find it does the opposite to me.”
“You say I’ve been married twice before but I’ve been married under circumstances where I was less informed than I am today,” Penn continued. “So I wouldn’t even consider a third marriage, I’d consider it a first marriage on its own terms if I got married again. I mean, I like the tradition.”
In 2018 Madonna and Penn’s relationship was explored in a Reelz documentary subtitled Irreconcilable Differences. And Rob Shuter, the founder of the Naughtygossip.com website, claimed in the show that the pair’s high profile worked against them. Referring to the constant press intrusion, Shuter said, “They were not following him because he won an Oscar, they were not following him because he’d made a great movie, they were following him because he was now Mr. Madonna.”
“I think the press and the celebrities have a difficult relationship, but they need each other,” Shuter went on to add. “The celebrities need us, we need them, and often we can find a way to co-exist together. With Sean Penn this never happened.” Indeed, Penn had built a reputation for refusing to play the fame game.
And any hopes for a romantic reconciliation appeared to have been dashed when Penn began stepping out with a much younger woman in 2016. Leila George, whose actor father Vincent D’Onofrio is only a year older than Penn, is still in the picture several years on. And in 2019 the pair were pictured sharing a romantic getaway in Italy.