Hugh Hefner’s Children Say He Was Very Different To The Man His Image Conveyed

Yes, we know what you’re thinking. “Hugh Hefner had kids?” It came as something of a surprise to us as well! We never really got that impression whenever the Playboy founder appeared in the spotlight. Anyway, he was a dad to four children in total: Christie, David, Marston, and Cooper.

So, what was it like to be the child of such a famous guy? Well, one thing’s for sure — the quartet were able to get remarkable insights into Hugh’s true character. And to them, he wasn’t just the happy-go-lucky entrepreneur rocking stylish dressing gowns. There was far more to him, as is underlined by their fascinating comments.

Hugh’s story began back on April 9, 1926. His parents Glenn and Grace Hefner welcomed him into the world that day, and then had another son, Keith, nearly three years later. From there, the future Playboy pioneer spent his formative years in Chicago, Illinois, showing flashes of his entrepreneurial spirit by starting a newspaper at Steinmetz High School.

A sign of things to come, right? Following his time in high school, Hugh then spent a brief period in America’s armed forces, taking on a “noncombatant” role during World War II. He moved on in 1946, ahead of attending the University of Illinois at Urbana-Champaign. Psychology was his chosen subject.

Hugh went on to bag his degree in 1949 — and this wasn’t the only big moment for him that year. You see, he tied the knot for the first time, too. Yep, the famous entrepreneur exchanged vows with a woman named Mildred Williams. And the milestones didn’t end there.

Some three years into their marriage, Hugh and Mildred added a new face to their family. Yes, Christie Hefner was born in 1952, and Playboy magazine then made its bow a year later. Talk about a life-changing chain of events! Yet that wasn’t all, as we’ll soon discover.

In the summer of 1955 Hugh and Mildred welcomed their second child into the world — David. His arrival coincided with the continuing rise of Playboy, which proved to be a huge hit at the time. To give you an idea of the numbers, even the debut edition boasted sales of over 50,000 when it dropped in 1953.

The adult magazine quickly turned into a juggernaut as the decade progressed, selling roughly one million units each month. The brand was growing at a frantic pace, but it wasn’t all good news for the Hefner family. A wedge started to form between Hugh and his spouse during that period.

The couple eventually split, finalizing their break-up in 1959. Mildred packed her bags for Wilmette, Illinois, along with young David and Christie. As for Hugh, he was now living in the original Playboy Mansion, which could be found in Chicago. So, how did that affect his relationship with the kids?

Well, Christie provided some insight on that front in Playboy’s January/February 2018 edition. This particular issue of the magazine came out just a few months after Hugh’s death in September 2017. She said, “I would see him a handful of times a year. We went for birthdays and Christmas.”

Christie also touched on her memories of the Playboy Mansion, recalling, “It was like a child’s dream because the house had a huge game room. To me it was a game house, with a pool table and a ping-pong table. And you didn’t have to put quarters in the pinball machines.”

“Every game [Hugh] owned had a board next to it where you put up the leading scores,” Christie added. “Everybody competed to get on or move up the board.” Anyway, as she and David grew older, the pair followed a similar path to their dad. Yes, they both went to college.

Christie went to Brandeis University, where she studied English and American literature. She successfully bagged her diploma during 1974. Meanwhile, her younger brother David earned a spot at the University of California Santa Cruz. Unlike his sister, though, he took classes focusing on digital media and film.

While that was going on, Hugh’s image as Playboy’s main man was being firmly established. From the dressing gowns to the ladies he surrounded himself with, the founder had become an iconic figure. He eventually left Chicago for Los Angeles, California, during 1975, moving into the Playboy Mansion West.

But around ten years later, Hugh experienced a pretty sobering health scare — he had a “minor” stroke. As a result of that, he made some important lifestyle changes, ahead of popping the big question to his long-term partner. From there, he and Kimberley Conrad tied the knot in 1989. She was also Playmate of the Year at the time!

Following the wedding, Hugh became a father again in 1990 with the birth of Marston Hefner. Then, just 12 months later, he and Kimberley had another baby boy together when little Cooper Hefner arrived. What a hectic period that must’ve been! How would the coming years compare to the past, though?

Well, unlike Christine and David, Marston and Cooper spent their younger years under their dad’s roof at the Playboy Mansion West. So they weren’t away from Hugh for lengthy periods. Yet the same couldn’t be said for the entrepreneur and his second wife. You see, they split up during the late 1990s.

Hugh and Kimberley’s marriage eventually came to an official end in 2010. As for their two children, Marston and Cooper went on to develop very different interests from each other. The older brother zoned in on writing, while his sibling earned a diploma at Chapman University and set his eyes on the business world.

In fact, Cooper followed a very similar path to his half-sister. He joined Playboy Enterprises and had become the “chief creative officer” by the summer of 2016 — more than 40 years after Christie bagged a job there. She was both the president and CEO at different points of the 1980s, before leaving in 2009.

Due in part to their respective positions at their father’s famous company, both Cooper and Christie have been in the limelight for a while now. That isn’t the case with David or Marston, though. Their chosen careers have veered away from the family business. It’s a pretty intriguing contrast, wouldn’t you agree?

Anyway, Cooper, who’s the spitting image of his late dad, found himself back under the microscope in January 2022. Why’s that? Well, Hugh’s youngest son took to social media at that time to defend the Playboy founder’s character against recent criticism. It made for fascinating reading, as you’re about to see.

“Some may not approve of the life my dad chose, but my father was not a liar,” Cooper wrote on Twitter. “However unconventional, he was sincere in his approach and lived honestly. He was generous in nature and cared deeply for people. These salacious stories are a case study of regret becoming revenge.”

While Cooper didn’t go any further regarding the “salacious stories,” the main body of his tweet might come as something of a surprise to you. Did you ever get those vibes when looking at Hugh’s happy-go-lucky public image? It seems significantly different, right? And Cooper isn’t the only one of Hugh’s kids to have discussed their dad’s character.

Going back to the Playboy interview from earlier, Christie also provided some eye-opening tidbits about Hugh. She shone a light on the type of parent he was to her, as well as his personality behind closed doors. It’s a proper deep-dive, folks, so we hope you’re ready!

Speaking about Hugh as a dad, Christie said, “[He was] kind of like a favorite uncle. Someone I knew absolutely loved me and would be there for me, but not someone who knew who my friends were or what I was interested in.” Something tells us their time apart might’ve played a role in that.

Regarding her face-to-face spells with Hugh, Christie referred back to the games room at the Playboy Mansion. She continued, “He would get the newest games, so that was the first time I saw Pong, Pac-Man, Frogger, and Donkey Kong. We’d have a lovely dinner and conversation, and then we’d play games. He was highly competitive with me and I with him.”

That “favorite uncle” tag’s starting to make a bit more sense, right? But away from the fun and games, we’re curious. How did Christie feel about the time they had together? Did she yearn to see more of Hugh? Well, that question was posed to her by Playboy, yet she focused on something else.

Yes, Christie zoned in on Hugh’s “shortcomings” as a person. She readily admitted to the magazine that her dad was far from perfect, but the former CEO apparently tried to roll with the punches in that respect. She found that age made it easier for her to “forgive” his personal faults.

“I’ve had this conversation with friends who have had challenging relationships with one or another parent,” Christie told Playboy. “The only thing I can say is what I feel. The other person isn’t going to change. That is who they are. With someone who’s genuinely abusive or a bad person, you should just get out of town.”

“But if they’re being the best person they know how to be, then you have to decide if there isn’t much there you can love,” Christie added. “And [you should] not become consumed with what they’re not able to give you.” Interesting stuff, right? It shows how complex parent-child relations can become!

At the same time, though, Christie did see slight alterations in Hugh’s behavior as he aged. And it’s fair to say they were pretty positive. For one thing, the famed entrepreneur wasn’t as close-guarded when it came to his feelings, leading his daughter to reiterate some of Cooper’s earlier words.

“How [Hugh] definitely changed was he found it much easier to express how important people were to him and how much he loved them,” Christie explained. “[That was] not just with family, but with other people he was close to. He was always a romantic, but that mostly manifested in his personal romantic relationships, as it would normally.”

“That softer side didn’t manifest itself so much in [Hugh’s] professional relationships,” Christie revealed. “He was always fundamentally a kind person, and I don’t want to say he became kinder or gentler, because he was never not those things. But as he got older, he became a softer version of himself. Maybe he came to realize how fundamental and essential human relationships are.”

Hey, we did say it was a deep-dive! Speaking of relationships, though, that brings us back to Hugh’s love life. Following his official split with Kimberely in 2010, the Playboy founder didn’t have to wait long for his next romance. Yep, he popped the big question to Crystal Harris that winter.

Mind you, it wasn’t plain-sailing. Going into the summer of 2011 Hugh’s partner apparently walked out on him, which suggested a third wedding was off the cards. Yet by 2012 the pair were back together again. They eventually exchanged their vows on New Year’s Eve. Talk about ending the year with a bang!

Hugh remained with Crystal up to his passing in September 2017. He was 91 years old. Unsurprisingly, it proved to be a tough time for all concerned, not least his four kids. But Christie raised a heartwarming point to Playboy about being part of a large clan when things get rough.

“We’re fortunate in my family because we really have three families,” Christie told the magazine. “My brother, David, and [I], the two boys, Cooper and Marston, from my dad’s second marriage, and my dad’s wife, Crystal. There’s huge mutual respect and love among all of us, so that’s a kind of funny support system, even though everybody has a different kind of grief.”

“I feel for the boys, because they had their dad for far fewer years than David and I did,” Christie continued. “And of course Crystal lost a husband. It’s not the same, but underlying it all we lost the same person whom we loved. The fact that we’re close and care so much about each other is a huge plus, and it’s something [Hugh] knew when he was alive.”

That must’ve been a nice feeling for Hugh, right? And the Hefner clan has expanded in the time since. Cooper and his wife Scarlett Byrne became parents during the summer of 2020, before having twins in March 2022. Given everything we’ve learned about the man behind the public image, we think he’d no doubt be bursting with pride.