Sean and Robin continued to raise their kids in northern California, where they moved after Robin was carjacked in L.A. in 1996, and work together as he launched a directing career, first with 1995's The Crossing Guard, then 2001's The Pledge. Sean won his first Academy Award for his role in Clint Eastwood's Mystic River in 2004, and emotionally thanked Robin in his speech. They were together in Cannes later that year (pictured), seeming happy, but the family hit a rough patch when Sean's younger brother, Chris, also an actor, died in January 2006.
Sean and Robin separated again in 2007, then reconciled four months later. Milk, the biopic about San Francisco councilman Harvey Milk that would win Sean his second Oscar, came out in 2008. Shortly after winning the Academy Award and this time failing to thank Robin, Sean filed for legal separation in 2009. That year Robin spoke to More magazine about her conflicting feelings about the relationship. "I hit that crossroad a while ago—for Robin [jabbing her hand at herself], the 'I know what I don't want' was flashing neon lights," she said. "I have no regrets. I, we, have two amazing children we raised together." The Truth About Robin Wright & Sean Penn's Split
This year Sean threw himself into relief work for victims of the January earthquake in Haiti, and reportedly began dating model Jessica White. Sean, who turns 50 this month, told Vanity Fair in July that Robin "is a ghost to me now." Robin is in the midst of a career renaissance, earning good reviews for her part in Rebecca Miller's The Private Life of Pippa Lee last year, and scoring roles in Robert Redford's The Conspirator and David Fincher's Moneyball.
One of our favorite people, Dan Savage, often says that we as a society tend to see a successful relationship as one where someone dies. Call us a bit nuts, but Robin and Sean's 20-year partnership seems to have been a pretty successful one, as neither of their kids grew up to be Tila Tequila, they produced a number of great films together, and they seem to have come out of it with a mutual respect, if not a warm friendship. Still, we're anxious to see who Robin will rebound with, because she seems awesome.
Photo via Bauer-Griffin.