At one point in Ben Affleck’s career, he was ‘one bad night away from a big E! True Hollywood Story’, or so he told Details. Wait, are we still talking about the same family man seen toting around his daughters, Violet and Seraphina? Yes, but Ben hasn’t always been so settled down. Bursting onto the Hollywood scene with Oscar-winning Good Will Hunting, an award he won alongside Boston best friend Matt Damon. His love life made tabloid headlines when he dated Gwenyth Paltrow in 1998 and ‘Bennifer’ counterpart Jennifer Lopez in 2002. Since then, Ben has found family and fatherhood with wife Jennifer Garner and has dipped into directing with Gone Baby Gone and most recently, The Town.