Notable Partners: Elizabeth McGovern, Madonna, Jewel Kilcher, Robin Wright, Elle Macpherson, Petra Nemcova, Natalie Portman, Jessica White, Scarlett Johansson, Garcelle Beauvais, Charlize Theron

After ending his marriage of almost twenty years to the smoking hot Robin Wright (that's Claire Underwood to all you newbies) at the top of the decade, the acting vet has been playing the field with actresses almost 15 years his junior. Going from a still stunning Robin Wright to the likes of Scarlett Johansson and Charlize Theron is enough to boister anyone to give very few fucks, an attitude that's seeped into Sean's middle-fingers-to-the-rules steez. This guy showed up to a Cannes Film Festival event looking like he was headed to a ranch or, gallery party in Williamsburg or something and completely killed it. Mid-life flourish would be the more appropriate term, no?