What’s It’s Like Being the Son of One of the Most Famous Sugar Daddies

Famous Sugar DaddiesImag­ine get­ting to spend every day around the Play­boy mansion—now imag­ine grow­ing up in it. That was the real-life expe­ri­ence of Cooper Hefner, the son of infa­mous sugar daddy, wom­an­izer, and Play­boy Enter­prises founder Hugh Hefner. Cooper is the youngest of Hugh’s four chil­dren. His mother is 1989’s Play­boy Play­mate of the Year, Kim­ber­ley Con­rad, who was just one of the famous sugar daddy’s younger lovers—she even­tu­ally became his sec­ond wife.

Con­trary to what many peo­ple think, Cooper says that grow­ing up in the Play­boy man­sion with a famous sugar daddy father wasn’t as out­ra­geous as you’d imagine—in fact, he insists that his life was pretty nor­mal, at least half of the time. When Hugh and Conrad’s mar­riage ended, the cou­ple sep­a­rated and the sugar daddy moved his wife out of the man­sion and into the house next door. “My brother and I had a room in each house. When my dad had par­ties, we stayed at our mom’s,” Cooper revealed in a recent inter­view. “As my brother and I got a bit older, around 14 or 15, we’d try to sneak into the par­ties but often we’d end up being chased by security,”—it turns out they really don’t let just any­one in to a Play­boy party.

When an older man has kids with a younger woman, many peo­ple ques­tion how the father’s age would affect his abil­ity to raise them. When Cooper was born, Hugh was about 65 years old, and it def­i­nitely affected their rela­tion­ship. “There were times where maybe I’d want to play base­ball with him and he wouldn’t want to do those things,” said Cooper. But that being said, Hugh knew how to make up for it. “I had the oppor­tu­nity to inter­act with peo­ple of all ages from all walks of life, which has given me the abil­ity to get on with anyone.”

So, how does Cooper feel know­ing that his father used to be one of the biggest sugar dad­dies around? He acknowl­edges it, but chooses to look past it. “We may be going through a time where it’s not very cool to have mul­ti­ple girl­friends but that is a part of our his­tory because of my father. My dad was a show­man, sure, but he was also involved with Jesse Jack­son and Mar­tin Luther King, pulling together in the strug­gle for the human rights move­ment in Chicago.”

Cooper, now 21, is fol­low­ing in his father’s foot­steps and is in the process of tak­ing over the Play­boy throne from his father. As alike as the father and son duo are, there are just as many dif­fer­ences between them. Cooper wants to take the com­pany in a dif­fer­ent direc­tion, one that today’s gen­er­a­tion can appre­ci­ate and relate to.

The other big dif­fer­ence? At only 21, Cooper has a long way to go before he can even come close to match­ing the women in sugar daddy Hef’s past. And he’s still got it. Cooper’s stepmother—Hugh’s cur­rent wife, Crys­tal Harris—is only six years older than Cooper.


“Cooper Hefner: My Play­boy dad Hugh and I don’t have the same taste in women,” Metro web site, August 27, 2013; http://goo.gl/6kzti5.

Woods, J., “The busi­ness of sex: Hugh Hefner’s youngest son embraces the Play­boy chal­lenge,” The Van­cou­ver Sun web site, August 27, 2013; http://goo.gl/OZ6pmC.

Photo Credit: Helga Esteb / Shutterstock.com