Top 20 Celebrities Who Had Relationships With Much Younger People

21. Hugh Hefner/Crystal Harris – 60

Hugh Hefner has basically spent his golden years bedding each and every one of his Playboy bunnies. He dates them by the bunch and keeps them living in his mansion. Hugh Hefner and Crystal Harris married when she was just 26 and he was 86. The 60-year age difference does not seem to matter as much as the money and lifestyle that he has to offer.