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Divorce Court: Who Won Sean Penn and Robin Wright’s Breakup?

Thanks to new, flashy relationships and the return of ‘House of Cards’ today, there has never been a better time to assess who’s won this celebrity divorce.

When a celebrity couple breaks up, there’s an initial deluge. The “he said, she said,” the list of alleged side pieces, the ensuing legal battle. If it’s a good couple, the breakup is enough to sustain a few weeks of tabloid covers, but then we’re all just expected to move on. Well, what if I haven’t? Some celebrity couples need to be revisited. Welcome to Divorce Court, a necessary forum to decide the winners and losers of the most high-profile and most interesting celebrity divorces.

“Robin Wright Penn” has a nice ring to it. Unfortunately for fans of that three-word consonance, it’s no longer a relevant name. Robin Wright and Sean Penn divorced in 2010 after 20 years of marriage, a rocky decade in the aughts, and several separations. Both Wright and Penn have been omnipresent in Hollywood for over 25 years, but thanks to new, flashy relationships and the return of House of Cards today, there has never been a better time to assess who’s won this celebrity divorce.

The Background

Sean and Robin first met while he was married to Madonna in the late ’80s. Their romantic relationship began, though, on the set of State of Grace in 1989, and they married the following year. They settled in Marin County in Northern California with their two kids: daughter Dylan, born in 1991, and son Hopper, born in 1993. And from that point, this marriage was turbulent, including many separations, subsequent reconciliations, and a couple of side relationships. During various hiatuses, Penn reportedly dated Jewel (1995) and Petra Nemcova (2008); further suspected philandering dogged him as well. (Remember that Sean Penn and Lindsay Lohan rumor?) Meanwhile, Robin, who had been an actor since she was a teenager, developed a reputation as cold, laconic, and selective with her projects.

I personally like to believe that the 1997 movie She’s So Lovely, in which they play a married couple plagued by the husband’s mental instability (as well as drug habits and low income), is an exaggerated depiction of their actual marriage. The fictional couple from the movie breaks up when Penn’s character goes to a mental institution, and Wright’s character moves on to marry a stable guy, played by John Travolta. Penn comes back 10 years later much more sane, and a love triangle ensues. In real life they were not (publicly) suffering from addiction and mental health issues, but they were not short on the drama. They first filed for divorce in December 2007, only to withdraw the petition five months later. They filed for a second time in April 2009, followed by a second withdrawal in May 2009. Ultimately, the third and final petition was filed on August 12, 2009, and the divorce was finalized in August 2010. (Note to People: There must be more photos of them to choose from.)

Current Estimated Net Worth

Robin: $60 million
Sean: $150 million
Winner: Sean. Numbers don’t lie, and thanks to for providing these figures. For context, Sean is richer than Nicole Kidman ($130 million), but way poorer than Tom Cruise ($250 million), the previous subjects of Grantland’s Divorce Court. Despite his reputation as a world-class actor, Sean has no sweeping epics or Baz Luhrmann spectacles to his name, so I’m surprised he bests Kidman. Robin is not even on the radar of riches with her paltry $60 million.

Worldwide Box-Office Gross Since Divorce

Sean: $346,906,247 over four movies. Even if you don’t know anyone who saw The Secret Life of Walter Mitty, it certainly helped pull up Sean’s numbers.
Robin: $343,796,158 over three movies. Robin’s return to film after the divorce may have been fairly slow, but Girl With the Dragon Tattoo and Moneyball made this race surprisingly tight.
Winner: Sean, by less than $4 million, though Robin’s per-film average is higher and there’s no financial accounting for the success of House of Cards. Sean actually has another victory over Robin. She doesn’t even have a dedicated page on, though he does.

Subsequent Relationships

This is where the story of Sean and Robin gets particularly interesting. For the last quarter-century, these two have been omnipresent, like the dull hum in a fluorescently lit room. Sean has been one of the best actors of his generation, involved in some capacity in a string of awards-bait movies (more on that below) for long enough that he is a fact of pop culture life.

Though she may not garner the same heightened praise, Wright is an icon thanks to playing Princess Buttercup in The Princess Bride and Jenny in Forrest Gump. And yet, their respective, dueling new relationships have made them both tabloid fodder for the last few months.


Kevin Mazur/Getty Images

Sean Penn is dating Charlize Theron. He’s 15 years older. This delicious scoop was initially confirmed by Piers Morgan and the Daily Mail, and photos of the new couple have been popping up all over. She is not his first post-Robin blonde. In 2011, Penn had a short relationship with Scarlett Johansson. He then dated PR gal Shannon Costello, who worked on his Haiti relief fund, and model Jessica White. As was not the case with those two women, Penn and Theron seem decidedly domestic. They go to the grocery store. They hang with her son. They make out in cars. They’re just like us!


David Livingston/Getty Images

Robin, refusing to be outdone, is engaged to Ben Foster. He’s not as famous as Theron, though he certainly deserves more acclaim for his turns in the 3:10 to Yuma remake and the ’90s teen adaptation of A Midsummer Night’s Dream, Get Over It. The latter was epic based on its cast alone. Foster has become the default super-intense guy in almost-great and aspirational movies. (His latest, Lone Survivor, is no exception.) Wright’s comments on their relationship only further this perception. In an interview with the U.K. Telegraph, Wright explained that the proposal was shocking but “we felt married anyway. We’ve been together ever since the first date.” They also have matching finger tattoos: She has a B tattooed on her left middle finger, and he has an R in the same spot. Matching tattoos for new couples have never been a bad idea.

Winner: Toss-up. Penn and Theron are the more powerful duo, but Wright and Foster are more surprising and seemingly more committed. After all, they are engaged with the ink to prove it. Wright and Foster are currently benefitting (by this rubric, anyway) from House of Cards’ second-season premiere. Their stock is artificially inflated by her cultural relevance in this exact moment. Penn and Theron, on the other hand, would command the paparazzi attention no matter what.

Awards and Critical Reception



Wright’s value as an actor may be at an all-time high right now. Thanks to her recent Golden Globe win, and flattering profiles in the aforementioned Telegraph and the New York Times, she is reemerging, this time with more ambition. The Times article explains how she aspires to direct, and it paints a portrait of a newly empowered woman. Wright also benefits from her choice to do the Netflix show at all, a decision she admits to being reluctant about initially.

The aughts were very good to Penn — Oscar-winning performances in Milk and Mystic River, plus a few other prestige movies like I Am Sam. (And fun fact: Penn and Theron both won Oscars in 2004.) But his résumé since the turn of the decade has been less impressive. There was last year’s Gangster Squad with Ryan Gosling and Walter Mitty, which came and went quietly and wasn’t even his movie as much as it was Ben Stiller’s. The main exception from a quiet decade so far is Terrence Malick’s Tree of Life. But unlike with Milk or Mystic River, Penn was secondary to the movie’s narrative. His biggest impact since divorcing Wright has been his work in Haiti after the devastating earthquake. His participation initially seemed suspect, a charity project that doubled as vanity project. But to his credit, he stayed committed to the effort even after the cause célèbre factor wore off. Despite his leftist politics, Penn’s work has even won him fans from the more conservative military.

Winner: Robin. She is doing all the right interviews, using the House of Cards press to reinvent her public persona. Wright has returned to the spotlight motivated and ambitious, and it’s hard to find a compelling critique of her right now. Penn, on the other hand, is best when he lets his work speak for him, and he has little to present from the last five years. When he does speak, it’s to disparage his marriage and say things like, “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.” That’s from an Esquire interview in December 2012. Maybe he should just stay in Haiti.

Miscellaneous Relevant Moment

Sean: Remember when he got into a feud with Wyclef Jean?
Robin: In case you missed it, Robin had a wardrobe malfunction at the Golden Globes. Boob tape!
Winner: Sean. Celebrity feuds are way more fun than boob tape in this post–Janet Jackson Nipplegate world.


Sean: Wyclef Jean accused him of abusing cocaine. But Wyclef’s comments were probably motivated by Sean’s extreme opposition to Wyclef’s attempt to run for president of Haiti.
Robin: Around the time the final, lasting divorce proceedings began, the National Enquirer claimed Robin was the one who finally had enough.
Winner: Robin. If the only rumors about you are about the divorce, it’s not so bad. Drug use, true or not, is far more salacious.


On this second-season premiere day of House of Cards, it’s hard to see beyond the show’s haze. Robin Wright seems to be everywhere. She does in fact spend her time all over the continent — in New York where she lives, in Baltimore where she shoots her TV show, in Los Angeles where her kids live, in Vancouver where Foster is filming. She’s used the Season 2 publicity campaign, bolstered by her Golden Globe last month, to reenter the pop culture landscape, and she even acknowledges her own renaissance. But will this be fleeting? Though Sean Penn hasn’t won or been nominated for an Oscar this decade, it seems quite possible he will be again. His sustained success is sufficient reassurance that he’ll rebound from this artistic dry spell. Perhaps Theron will reawaken his artistic interests. But if I am judging solely on the time since divorce, Robin has steadily worked her way into our consciousness. She cannot be denied.

Final Verdict: Thanks to David Fincher, who cast her in Dragon Tattoo and convinced her to do House of Cards, Robin Wright is the winner of this Divorce Court.