Sean Penn and Robin Wright – $215 Million

Sean Penn and Robin Wright started dating in 1989. They have two kids, Dylan and Hopper Jack Penn. Like other couples, they have experienced many struggles when it comes to trying to keep their relationship steady. Even if they tried to save their relationship many times, it just wouldn’t work, so they eventually parted ways. They worked at co-parenting their children as both grew up, but these days? Both Dylan and Hopper are more than capable of looking after themselves.

Considering the investments made by their parents, they have little to worry about in the future. This is timely since Penn has also retired from the entertainment industry and is focusing on his novel. His book, Bob Honey Who Just Do Stuff, is what keeps him busy today. On the other hand, Wright is focusing on her acting and directing career. She is an award-winning actress and continues to work on TV.