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Big Love, Big Split for Charlize Theron and Sean Penn

The Daily Beast

June 18, 2015

We don’t know why they broke up yet, but before details of any possible gruesomeness engulf us, a moment of pause for the recently separated Sean Penn and Charlize Theron—a Hollywood coupling of a year-and-a-half’s standing, and one of the “more interesting than most” variety.

In its story breaking the news, US Weekly said the engaged couple had called it quits after this year’s Cannes Film Festival, where they had posed on the red carpet at the premiere of Theron’s much-acclaimed Mad Max: Fury Road.

Who knows if Cannes—a bloated, weird fandango of a film festival, survivable only by consuming gallons of rosé—was partly to blame, but remember that this is the place where women are forced to wear high heels on red carpets. Anyone in flats is made to lick the garbage cans along the Croisette.

A friend wondered at the age difference, but although Penn, 54, may occasionally sport the heavily whiskered face of an ancient mariner (married to the hot body of a 22-year-old CrossFit addict), Theron is 39 herself. She looks a lot younger, for sure, but that’s hardly May to December, more like May to early August.

In a March cover profile, Esquire U.K.’s Alex Bilmes noted of Penn that he was “not tall—maybe 5ft 9in—but he is physically imposing: brawny and with an off-balance buccaneer’s stride that speaks of a life lived not behind glass and under strip lights but somewhere Out There, where the sun beats down on a man’s leathery hide and the wind whips through his thicket of dark hair and the years of exposure to the elements carve deep lines across his brow.”

So, weather-beaten, hard-living Penn versus the beauteous Theron; beauty and a quite sexy beast; two actors whose résumés show they are not beholden to mega-franchise filmmaking but instead are dedicated to standout roles distinguished by their intensity.

Theron won a Best Actress Oscar in 2004 for her astonishing portrayal of serial killer Aileen Wuornos in Monster, while Penn is an acclaimed actor and director, having moved on from his ’80s incarnation of brawling tearaway, who dangled a paparazzo out of a ninth-floor window in China.

In 2010, he reached a plea deal to settle charges that he had attacked another paparazzo in Los Angeles.

Penn can still glower at the flashbulbs, even on the red carpets he frequently inhabits. He won his first Best Actor Oscar the same year as Theron for his role in Clint Eastwood’s brooding abuse drama Mystic River; the second for his brilliant and moving portrayal of the assassinated gay civil rights hero Harvey Milk in Gus van Sant’s Milk (2008).

In recent years, matching his artistic endeavors has been Penn’s humanitarian and political efforts—from his work in New Orleans after Hurricane Katrina in 2005 to overseeing a tent camp after the 2010 Haitian earthquake.

There have been more controversial interventions, such as Penn’s calling in 2010 for the arrest of journalists who called then-Venezuelan president Hugo Chávez a dictator.

Tabloid readers will have become used to seeing Theron and Penn looking good together on red carpets and beyond.

In April, they were photographed, very loved-up—doing their own version of Burt Lancaster and Deborah Kerr in From Here to Eternity—on a Malibu beach. Penn also seemed close to Theron’s son Jackson.

US Weekly says the couple had known each other for decades and got engaged on a trip to Paris last December. It was Theron who broke off the relationship, the magazine said, which would sadly concord with what seemed like Penn’s full-hearted endorsement of the relationship in Esquire U.K.

He told the magazine in March that he was “in love” with Theron, that he would get married again: “You say I’ve been married twice before but I’ve been married under circumstances where I was less informed than I am today, so I wouldn’t even consider it a third marriage, I’d consider it a first marriage on its own terms if I got married again.”

After failed marriages to Madonna (which was famously tempestuous) and Robin Wright (with whom he has two, much-loved children), Penn said he was “surprised to be in love. Lot of reasons. I’m self-proclaimed bad at mathematics but I can do two plus two: 53 years old plus finally beginning to figure out why you haven’t been happy in a single relationship? It could seem too late. But to run into somebody now who you care about is a much more passionate, deeper, truer and—God!—a much happier feeling. It’s a lot more romantic and a lot more fulfilling to be in a relationship and to think you’re a good person within it.”

Then, in May’s Esquire, Theron—a cover star like her then-partner—said their friendship of many years had stemmed from respect; much from her as she didn’t have an equivalent body of work to his.

Love and a passion for making films had been their bond, Theron said, but also Penn’s well-known humanitarian work.

“A lot of people want to tell you the answer to solving all of Africa’s problems from what they’ve seen on CNN. Sean is not that guy. When he started working in Haiti and I started working on the AIDS front in South Africa, we spent a lot of time talking about those worlds,” Theron said.

The possibility of a relationship had never struck either of them, she added: “Just when you think you know how things are supposed to go down, life just kicks you in the ass and guess what? You don’t have a clue.”

The fact that friendship predated the romantic relationship was nice, and gave the latter “weight” and a “foundation,” she said.

The couple was living in the moment, which was “just really good. It’s really good, really nice. The marriage thing is always so strange to me anyway. I love the possibility of anything, but I’m really enjoying myself and the everyday moment and how that coincides with my son and my life and my friends. I’m a very, very, very lucky girl. Very lucky.”

The writer then ventured that Penn was looking “craggy,” although it is unclear whether the writer said that to Theron.

She said, apparently enthusiastically: “He’s hot. He is hot. How do you say that in an interview?”

Theron likened the relationship to “when somebody walks into your life and makes you see something that you really never thought you’d be able to see. If somebody had said to me, ‘This is what it will be,’ I would’ve said, ‘Fuck off.’ As you can see, it makes me smile.”

So, safe and sad to say (unless their words in both interviews were carefully crafted spin—which seems highly unlikely), whatever has happened between Theron and Penn must be fairly major and traumatic.

Perhaps a hint came in a June interview Theron gave to Elle, in which she talked about Penn alongside such matters as the Hollywood gender pay gap—which she recently successfully confronted by insisting on an equal (reportedly $10 million) fee to her male co-star Chris Hemsworth on The Huntsman.