Hugh Hefner and Crystal Harris

Alright, lets get the most extreme couple out of the way first. Most of you probably knew that good ol’ Hugh would be on this list but did you know that Hugh was 60 years older that Crystal Harris when they got married! He was 86 and she was 26. Yikes! She’s more than 30 years younger than his two oldest children and only a few years older than his two youngest ones… talk about awkward.