#7: Hugh and Crystal Hefner

Playboy creator and overall household name, Hugh Hefner was notorious for dating women almost half his age. It always seemed like the older he got, the younger the women he dated would be. Throughout his entire life, especially during his time in the Playboy mansion, Hefner always had women much younger than him around.

Crystal Hefner was Hugh’s most recent wife, to whom he was married right before he died. You might want to hold onto your seat for this one because Crystal was 60 years younger than Hugh. Again, it should come as no surprise but it certainly raises questions about the balance of power that existed in his many relationships with women who were half his age.