Dating: Hugh Hefner
Age difference: 60 years
Hugh Hefner is such a titan of cradle-robbing it's hard to even compare him to the rest of this list. Going back to Kimberley Conrad, the wife he married in 1989, even she was 36 years younger than he. His love life has been a constant cycle of trading in slightly older young ladies for young young ladies, the epitome of Wooderson's observation in the movie Dazed and Confused: "I get older, they stay the same age."