Robin Wright and Sean Penn – 14 Years Together

Hollywood loves a dramatic couple, and Robin Wright and Sean Penn delivered for two whole decades. They met in the late 1980s, back when shoulder pads were big and so, apparently, was their love. Their relationship was a rollercoaster—together, then apart, then back together again like a boomerang that couldn’t quite make its mind up. In between breaks, they managed to squeeze in a wedding in 1996 and even had two children together.

They finally called it quits in 2010, though rumors of reconciliation swirled around them. Maybe they’re just the ultimate Hollywood exes—proving sometimes family bonds are stronger than romantic ones.