44. 1970s: Hugh Hefner with a Catch
Straight men have been envious of the ultimate Playboy Hugh Hefner for as long as he has been around. He has never had to try too hard to get what he wants, and here we see him with the catch of the day and Barbi Benton, who was also a catch, along with friends on a boat having a ball. He was a good-looking devil, wasn’t he?
43. 1960s: Hillary Rodham Clinton Getting Her Face Painted
Before she became the First Lady of the United States and then the 67th Secretary of State, Hillary was just an ambitious college student like most politicians. Today, Hillary Clinton gets in a lot of trouble for not showing enough “emotion” and “candor.” But here you go, this is a candid shot from the ’60s of Hillary Rodham during a face-painting session at Wellesley College.