The trailblazing media icon wed three times and fathered four children — the most prominent of which, currently, is his youngest: 26-year-old son Cooper, the chief creative officer of Playboy Enterprises

It’s been almost three months since Hugh Hefner, the founder of Playboy magazine and star of E! reality show The Girls Next Door, died at 91.

Both lauded and criticized over the span of his revolutionary career, the trailblazing media icon wed three times and fathered four children — the most prominent of which, currently, is 26-year-old son Cooper, the chief creative officer of Playboy Enterprises.

In newly uncovered trust documents, Hefner clearly outlined the beneficiaries to his estate: widow Crystal Hefner and his children Christie A. Hefner, David Hefner, Marston Hefner and Cooper — but he insisted that if any of them frequently use illegal substances or become dependent upon alcohol or any legal drugs, they will be suspended from it.

Read on for the full picture of Hefner’s family tree.

Cooper Hefner

“My father lived an exceptional and impactful life as a media and cultural pioneer and a leading voice behind some of the most significant social and cultural movements of our time in advocating free speech, civil rights and sexual freedom,” Cooper said in a statement after his father’s death. “He defined a lifestyle and ethos that lie at the heart of the Playboy brand, one of the most recognizable and enduring in history. He will be greatly missed by many, including his wife Crystal, my sister Christie and my brothers David and Marston, and all of us at Playboy Enterprises.”

Cooper joined the family business at the age of 21. In 2015, he left the company for 18 months, a decision precipitated by boardroom battles over the company’s direction. He returned in June 2016 and was recently named chief creative officer, with plans to rebrand Playboy for his own generation.

“Yes, there are lifestyle components to Playboy, but it’s really a philosophy about freedom,” he told The Hollywood Reporter in August. “And right now, as history is repeating itself in real time, I want Playboy to be central to that conversation.”

60th Anniversary Playboy Party
Cooper Hefner
| Credit: Taylor Hill/FilmMagic

“I suit up in my dad’s pajamas for our Midsummer Night’s Dream party; it’s a nice note to the past,” he continued. “It would be a major mistake — ridiculous — to wear them to the office. I think about the Playboy philosophy constantly, but I have my own point of view. It’s what will have to carry me through.”

Parents Grace & Glenn Hefner

Born in Chicago in 1926, Hugh was the older of two siblings, with an accountant father and a stay-at-home mother, who were both conservative Protestants from Nebraska.

He has attributed his rebellion to his parents’ emotional restraint, telling THR in 2011, “My folks were raised pure prohibitionist. They were very good people, with high moral standards — but very repressed. There was no hugging and kissing in my home.”

Grace and Glenn Hefner
| Credit: Hugh Hefner/Instagram

Brother Keith Hefner

Hugh’s younger brother Keith was a longtime executive at Playboy, handling the training of Playboy Bunnies as well as model recruiting.

Keith died at 87 on April 8, 2016 — one day before Hugh’s 90th birthday. Hugh confirmed the news on Twitter, sharing a photo of the pair and writing, “This morning, my dear brother and best friend passed away. I love you, Keith. Rest in peace.”

First Wife Millie Williams

In 1949, Hugh married his first wife, Northwestern University classmate Millie Williams. The two met while Hugh was taking a semester of graduate courses in sociology. Though prior to tying the knot Williams admitted to having an affair during Hugh’s time in the Army, their marriage lasted for 10 years and they had two children, daughter Christie and son David.

Millie Williams and Hugh Hefner in 1994
| Credit: Hugh Hefner/Instagram

In a 2007 interview with the Daily Mail, Hugh said he lost his virginity to Millie.

“I think the relationship was probably held together by two years of foreplay,” he said. “That wasn’t unusual for our time. In fact, most of my immediate friends didn’t have sex until they married. Millie and I had it just before.”

“I had literally saved myself for my wife, but after we had sex she told me that she’d had an affair,” he continued. “That was the most devastating moment in my life. My wife was more sexually experienced than I was. After that, I always felt in a sense that the other guy was in bed with us, too.”

Daughter Christie Hefner

Christie, Hugh’s first child — and only daughter — began working for Playboy Enterprises in 1975. She was named company president in 1982, and then chairman and chief executive executive officer in 1988. During her time at the company, she transformed the brand into a global giant, shutting down the original Playboy Clubs — a chain of nightclubs featuring waitresses dressed in Playboy bunny costumes — and helping launch Playboy TV and

In a 1979 interview with The New York Times, Hugh called his daughter “the brightest, most articulate 26-year old lady I have ever met” and addressed speculation that she became the figure-head of the company as a way of defusing feminist criticism of the magazine.

“Well, I have made the comment that [if] Christie hadn’t existed, our promotion department might want to invent her,” he said. “She’s rather ideally suited, both symbolically and actually, for the role that she’s playing in the company and the role that I hope she will play in the future.”

“I think feminist opposition is lessening, tell you the truth,” Christie told the newspaper. “I think they’re finally realizing Playboy is not the enemy, it’s a friend. They’re realizing it’s a men’s magazine. It doesn’t deal with all that it means to be woman. That’s not its mission in life, any more than the women’s magazines deal with the complexities of being man. In fact, part of the problem is that they don’t even deal with the complexities of being a woman. I’m a lot more anxious to change what’s going on in Cosmopolitan and Family Circle magazines than I am in Playboy, as far as roles for women are concerned.”

6th Annual Elly Awards Luncheon
Christie Hefner in June 2016
| Credit: Paul Zimmerman/WireImage

Asked if it would bother him to see Christie as a nude Playboy centerfold, Hugh said no.

“It’s not likely to happen, but it wouldn’t bother me,” he said. “She’s certainly beautiful enough, but she’s found another road that makes me much happier.”

Christie, now 64, stepped down from her position at the company in 2009. She is currently the chairman of Hatch Beauty, a brand and innovation strategy company, and is heavily involved in charity and political organizations.

Cooper regularly seeks counsel from his half-sister, telling THR in August that she “can relate to the situation more than anyone could” and urges him to keep a clear head in business discussions.

“For me as a [26]-year-old, that’s sometimes challenging,” he admitted. “My emotions get the best of me.”

Son David Hefner

Hugh’s oldest son David, 62, is the most private member of the family. He has remained entirely out of the spotlight and away from the Playboy lifestyle. Little is known about his career path, though he reportedly has worked as a computer programmer.

In 1979, Hugh told The New York Times that it didn’t bother him that his son doesn’t use his last name. (Christie and David adopted their stepfather’s name at a young age, though Christie began using Hefner again as a junior in college.)

“In the case of David, no, that doesn’t disturb me,” he said. “Because society’s expectations are so different for men and women, I think it is much more difficult to be my son than my daughter. I don’t think it reflects any separation from me, but rather a need at this particular point in his life to be himself. And that I respect.”

Very few pictures of David are publicly available, though in August, Hugh’s son Marston tweeted a photo of David enjoying a game of backgammon with his father and sister Christie.

Second Wife Kimberley Conrad

A 63-year-old Hugh wed 26-year-old Conrad in July 1989 after they met at a Playboy shoot two years prior. They had two sons, Marston and Cooper.

Hugh and Conrad separated nine years later, and she moved into a $7 million home next door to the Playboy Mansion, bringing the couple’s young sons with her.

Performance of "Phantom of the Opera"
Hugh Hefner and Kimberley Conrad in 1989
| Credit: Ron Galella, Ltd./WireImage

“Kimberley is the love of my life, but there was a growing difference in terms of interest,” Hefner told PEOPLE at the time.

“I love Hef deeply,” she added. “But we’re on different schedules. I like going to bed at 10 [p.m.] and getting up at 6:45 [a.m.] to work out; he likes watching movies [sometimes until 1 a.m.]. Sometimes you want to go downstairs and have quiet, as opposed to running into 50 people. I just wanted a change.”

Conrad and Hugh remained legally wed for nearly 20 years. He finally filed for divorce in 2009 — just weeks after Conrad sued him, claiming he owed her $5 million under their prenuptial agreement and for proceeds from the sale of a home they shared. (The property in question was the home adjacent to the Playboy Mansion, where Conrad previously lived and which sold for $18 million.)

At the time, Hugh denied that he owed Conrad any money, telling PEOPLE he faithfully paid her $250,000 a year as promised in their prenup.

“I would’ve been happy to divorce her when we separated,” he added. “But she wanted to remain married for our boys.”

Their divorce was officially finalized in 2010, according to TMZ, who reported the former couple came to terms on a confidential property settlement.

Son Marston Hefner

Hugh’s first son with Conrad, Marston, now 27, lived in the Playboy Mansion for the first eight years of his life, until he moved in next door with his mother.

“Well, as a 15-year-old kid, seeing naked people occasionally, that’s — it’s just the lifestyle of growing up as Hugh Hefner’s son, in his shadow,” an 18-year-old Marston told GQ in 2008. “It’s not a boo-hoo sob story. But it’s not the same as every other kid. … It’s easy to tell who wants to be your friend for those reasons and who doesn’t. People find out and they’re like, ‘Oh, my God, Hugh Hefner is your father. You’re a god.’ And I’m like, ‘All right, I’m a god. Yeah. I’m a god.’ ”

“My, like, expectancy for what girl I’m going to get is, like, so f—ed up,” he said. “I’ve just been around really hot women my entire life, so the average high school girl won’t do it for me. But instead of making me really care about looks, I look for the personality and a personal connection. Because I’ve been around looks all my life, and it’s like, if I can’t talk to her…”

“The ones I find attractive are [brunette], blue eyes, and that’s about it. An intelligent woman that I can have a conversation with,” he added. “That centerfold in the magazine probably wouldn’t be my girlfriend, because I wouldn’t find her attractive. I don’t care about fake boobs if the girl has a good personality, but most girls with fake boobs I don’t find attractive — because of why they got the fake boobs in the first place.”

Hugh told the magazine that Marston “thinks of himself as Hef junior.”

“First of all, he’s the firstborn, and he’s very much aware of that,” he said. “With Marston, I was there, a hands-on father. As you look at the first version of that documentary on my life that A&E did, called American Playboy, you can see the children’s toys in the great hall. And Marston was a big fan of Batman, so I showed up one afternoon unexpectedly in a Batman costume and tried to convince him I was Batman!”

In 2012, 21-year-old Marston was arrested for allegedly attacking his live-in girlfriend, Playboy Playmate Claire Sinclair. He was later released on $20,000 bail on the misdemeanor offense, according to Pasadena police.

Marston was sentenced to 52 weeks in a domestic violence program, according to TMZ. He was also reportedly ordered him to stay away from Sinclair for three years.

Though he was initially positioned as a co-heir apparent, he’s remained mostly out of the public eye since the incident, and according to THR has recently been teaching English in Japan.

“My dad was public about wanting us to run the organization together,” his younger brother Cooper told the magazine in August. “But it became evident as we got older that it was not something that spoke to him.”

Third Wife Crystal Harris

Hugh’s third wife was Playmate Harris, whom he wed on New Year’s Eve in 2012.

Octogenarian Playboy founder Hugh Hefner poses with his bride Crystal Harris and dog Charlie at their New Year Eve wedding in Beverly Hills
Hugh Hefner and Crystal Harris on their wedding day
| Credit: REUTERS/Elayne Lodge

The two — who had a 60-year age difference — first got engaged in 2010, though Harris called it off four days before their planned June 2011 wedding.

They later reconciled, and set a new date after his divorce from Conrad was finalized.