Though most people remember Hugh Hefner as the face of Playboy, the fact is, he was also a dad. Hugh was the father of four children, whose mothers (two each) were ex-wife Mildred Williams and Kimberley Conrad.
Hef's youngest son, Cooper, was born in 1991 to mom Kimberley, but as fans already know, the family-man lifestyle didn't seem to last long. The couple was separated as early as 1998, though their divorce wasn't finalized until much later.
In fact, Hefner filed for divorce the same year that Cooper turned 18, noted Reuters. The publication recapped that Kimberley and the boys lived next door to the Playboy mansion for all the years in between, while Hefner remained married to Conrad.
At the time, Hefner talked about how happy he was to no longer be married, elaborating that he only stayed married to her "for the sake of the children, at her request." But what happened to Hugh's two sons, and specifically, the younger child whose 18th birthday triggered the apparent breakdown of his parents' 'arrangement'?
While it seemed that Crystal Hefner, Hugh's wife at the time of his passing in 2017, struggled with her "identity" after Hef was gone, his children are doing pretty well for themselves.
The 29-year-old may have grown up next door to the Playboy Mansion, but his time with the company wasn't as smooth as fans may have expected from the Hef's youngest boy. Cooper left the company after college, because of disagreements with the then-CEO, but he returned as the chief creative officer later.
As the NY Times reported, Cooper Hefner was the creative mind behind Playboy's inclusion of a transgender Playmate on the cover in 2017. It was the first issue after Hef's passing, noted NY Times, and Cooper's statement at the time was that "It’s the right thing to do. We’re at a moment where gender roles are evolving."
But at the same time, Cooper and his dad seem more aligned in their desires for the company's branding than onlookers may expect. NY Times confirmed that the cover model for that particular magazine issue had been in Playboy's pages before, and she was selected as the cover model months before Hugh passed away.
At the same time, Cooper is different from his father in many ways. For one thing, his life isn't the picture of opulence (remember Hef's car collection?). After that pivotal moment at Playboy, Hefner stepped down as chief of global partnerships. He was married in 2019 and has a child who was born in 2020. At the time of his resignation, Cooper announced he had plans to launch a media company.
But then he enlisted in the United States Air Force, noted Fox News, in a vastly different life path than the one his father traversed, or what he had planned for.