Reported affairs: 1
Restraining orders: 0
Sean Penn slowly shed his bad-boy image throughout the 1990s, and his marriage following a long courtship to actress Robin Wright in 1996 solidified his toned-down attitude. Despite having two children together and a period of apparent calm for roughly a decade, the couple grew apart in the late 2000s—fueled in part by
rampant rumors of an affair between Penn and Natalie Portman—and finally split for good this past summer.