Sean Penn and Leila George (32 Years)
In his lengthy career in Hollywood, 62-year-old Sean Penn has made the rounds with the ladies. From his often publicized, tumultuous relationship with Madonna, to his marriage and divorce from Robin Wright Penn, Sean has done just fine. And Penn has kept the streak going with Leila George, the beautiful, 30-year-old Australian actress. Unfortunately, George surprised Penn with divorce papers a year into their nuptials, with Penn admitting that the combination of alcohol, drugs, and his obsession with politics ruined their union.