In 2016, Cooper, the youngest of Hef's four children and son of his second ex-wife and 1989 Playmate of the Year Kimberley Conrad, replaced his dad to become Chief Creative Officer of Playboy Enterprises. The now 26-year-old oversees all the company's creative divisions, which includes print and digital content—namely Playboy magazine, and events.
"One of the great questions was, 'At 86, what happens after Hef is gone?' And I think we see the answer in my son," Hef told WSJ Live in late 2012.
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In 2011, at age 19, Cooper told CNN that he and his dad talked about him getting involving in the family business.
"We've talked about it and I definitely would love to be involved when I'm older," he said.
In 2012, at age 20 and still a student at Chapman University, the younger Hefner began to get more involved in the business. That year, he represented the brand at the opening of a new Playboy Club in London (he returned there two weeks ago) and the annual Playboy Jazz Festival.
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At the time, Cooper said he was focusing primarily on college but was also learning about how Playboy operates.
"So, sitting down, talking to executives, explaining different fields, ‘cause that's kind of what you need to do with a company this large," he told WSJ Live.
"Well, I let him hang out a lot," Hef said. "And he does that very well."
Cooper soon began participating in board meetings as a nonvoting observer, spurred by anxiety about his father who had started to stay away from the spotlight amid declining health, according to The Hollywood Reporter.
Cooper told the outlet this past summer that Hef initially hoped both he and his brother Marston Hefner, 27, would run Playboy together.
"But it became evident as we got older that it was not something that spoke to him," Cooper said.
Cooper signaled that the Playboy founder did not pressure him into following in his footsteps, saying he has "always been somebody who's advocated, 'Follow your own dreams.'"
"I mean, I'm not here because I have to be, I'm here because I want to be here," Cooper said.
He also said he regularly seeks counsel from his half-sister Christie Hefner, 64, who served as chairman and chief executive of parent company Playboy Enterprises Inc. for more than 20 years until 2009.
"She can relate to the situation more than anyone could," he told The Hollywood Reporter.
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As Chief Creative Officer, Cooper helped bring Playboy back to its roots, to what it's known for. In 2017, the company announced that the magazine will being back nude pictorials after axing them about a year prior.
"I'll be the first to admit that the way in which the magazine portrayed nudity was dated, but nudity was never the problem because nudity isn't a problem," Cooper said in a statement at the time. "Today we're taking our identity back and reclaiming who we are."
"That was our April Fool's joke for the last year," Cooper joked to E! News' Carissa Culiner this past April. "We were just playing a really, really sick joke. We thought, 'Hey, let's take the nudity out for a year and then bring it back around April. It was funny, right?"
Cooper has also worked for Playboy as a writer, contributing articles (yes, the joke is timeless; Playboy does have articles) and video reports, delving into topics of masculinity, religious and even politics and becoming a voice for his Millennial generation. Like his father, he is an outspoken supporter of LGBTQ rights.
Such articles include "Trump's Transgender Remarks Prove Again How Unpresidential He Really Is," "Religion Needs a Re-Brand for Millennials" and "The Story of a Millennial Who's Undocumented: Illegal in the U.S."
"Yes, there are lifestyle components to Playboy, but it's really a philosophy about freedom," he told The Hollywood Reporter. "And right now, as history is repeating itself in real time, I want Playboy to be central to that conversation."
As for his personal life, Cooper isn't following in dad's footsteps entirely, for now. No multiple girlfriends for him.
"I think that's entirely up to him," Hef told WSJ Live.
Since 2015, Cooper has been engaged to actress Scarlett Byrne, who played Nora Hildegard on The Vampire Diaries and Pansy Parkinson in the Harry Potter films. Earlier this year, she posed nude for Playboy.