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Let's face it: Hugh Hefner is a freak, in the most enviable way possible. We may never see someone quite like Hugh Hefner again, but that doesn't mean cradle-robbing isn't a popular practice for men.
And seeking mates with that father-figure quality (evolution makes them want reliable providers, y'know) continues to occur in the female of the species.
Many of Hollywood's leading men have married much younger women.
Hugh Hefner married Crystal Harris on December 31, 2012 when he was 86 and she was 26. Other famous men who have married much younger women include Frank Sinatra, Kevin Costner and Woody Allen.Age: 71 Birthplace: Waco, Texas, United States of America Profession: Comedian, Television producer, Musician, Film Producer, Screenwriter, more Credits: The Jerk, ¡Three Amigos! This was Ruiz's first marriage, and Eastwood had been married once before., Bowfinger, Shopgirl Also Ranked #20 on The Most Trustworthy Celebrities in the World #7 on The Funniest People of All Time #97 on Celebrities Who Should Run for President #8 on The Funniest Stand Up Comedians of All Time Clint Eastwood married Dina Ruiz on March 31, 1996, when he was 66 years old and she was 31. List of Famous Women Who Married Older Men ranked by fame and popularity.It is quite common for women to marry older men, and several of Hollywood's most famous actresses have done just that.