Hollywood Odd Couples: Past & Present
Cher & Tom Cruise
This relationship was kept secret for years and when this May/December romance was finally revealed it was quite the shocker! In 2008, Cher told Oprah while a guest on The Oprah Winfrey Show that she dated the much younger Tom Cruise when he was just a "shy boy." The singing icon said of Cruise, "He was so wonderful. And I was so crazy about him." Cher told Oprah, "And he was so, like, different. He was a shy boy. He didn't have any money." The former couple has a 14-year age difference.