This is the family Hugh Hefner leaves behind

The robes, the captain’s hat, the bevy of busty blondes — Hugh Hefner certainly was a recognizable character, whether he was on TV, magazine covers, or the red carpet. Following his death on Wednesday, which came as he was surrounded by loved ones at the Playboy Mansion, Yahoo Lifestyle takes a look at the family he left behind.

Hugh Hefner and his son, Cooper Hefner, at the 2014 Midsummer Night’s Dream Party at the Playboy Mansion. (Photo: Christopher Polk/Getty Images for Playboy)

Wife No. 1
Hefner’s first love was his high school sweetheart, Mildred “Millie” Williams. Williams is who he lost his virginity to, and their relationship ultimately served as a foundation for what would become his Playboy empire.

“I think the relationship was probably held together by two years of foreplay. That wasn’t unusual for our time. In fact, most of my immediate friends didn’t have sex until they married. Mill[ie] and I had it just before,” Hefner recalled to the Daily Mail in 2007.  “I had literally saved myself for my wife, but after we had sex, she told me that she’d had an affair. 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.”

Millie and Hugh on their wedding day. (Photo: Twitter)

Still, the pair got married and had two children before divorcing in 1959. But it’s doubtful Hef had hard feelings toward his ex-wife, as he was known to post various throwback pics of her on social media.

The Hefner Children, Part 1
Hefner’s oldest children from his marriage to Williams are Christie, 64, and David, 62. Christie was very involved in the family business, working at Playboy for more than 30 years and serving as CEO for 20. In 2009, she stepped down and got involved in various charities, working to advocate for the empowerment of women in the workplace. She credited the election of President Obama as her inspiration. “Just as this country is embracing change in the form of new leadership, I have decided that now is the time to make changes in my own life as well,” she said at the time.

Christie Hefner and her dad. (Photo: Jamie McCarthy/WireImage)

As for David, he has chosen to stay out of the limelight and the family business. There is not much known about him or what he does, and very few photographs. In 2012, Hefner tweeted a photo with David, but deleted it.

Hugh Hefner and estranged wife Kimberley Conrad Hefner in 2003. (Photo: Frazer Harrison/Getty Images)

Wife No. 2
After a minor stroke in 1985, Hef decided to tone down his wild parties (a bit) and even settled down. The following year, he married Playmate of the Year Kimberley Conrad, who was 36 years his junior. They had two sons, Marston, 27, and Cooper, 26. The couple split in 1998.

Hefner alleged to the New York Times that while he was faithful, Conrad was not. But they remained friends, and when Conrad moved out, she just moved next door. It wasn’t even until nearly a decade later, in 2009, that the Playboy founder filed for divorce.

The Hefner Children, Part 2
Both boys grew up at the Playboy Mansion; however, Cooper is much more involved with the brand. While he’s really become the face of Playboy Enterprises, his official title is chief creative officer. He’s also the founder and former CEO of the upstart media company Hop and is a member of the California State Military Reserve. Cooper issued a statement about his father’s passing and has also been an unofficial media liaison ever since Hefner first faded from the spotlight.

Marston Hefner and his father in 2011. (Photo: Ethan Miller/WireImage)

Marston also has had a media presence, but for the wrong reasons. In 2012, he was arrested after allegedly attacking his girlfriend, Playmate of the Year Claire Sinclair, and was sentenced to a domestic violence program for one year. In 2016, he was also busted for DUI.

All four of Hef’s kids appear to be close. Last month, Marston shared a photo with his father, Christie, and, we assume, David.

Wife No. 3
As they say, third time’s the charm, and Hefner believed he’d found his perfect partner in wife Crystal Harris. However, their relationship wasn’t without its ups and downs.

Hef and Harris — who is 60 years his junior — announced their engagement in December 2010. Just days before the ceremony in June 2011, the Playboy model called off the wedding. Shortly after, she did various interviews about their split, including one with Howard Stern during which she insulted his skills in the bedroom. Hef tweeted his disappointment and sadness, saying, “I feel sorry for Crystal. She seems lost.”

Crystal Harris and Hugh Hefner in 2013. (Photo: Charley Gallay/Getty Images for Playboy)

But what’s lost again is found again. Nearly a year later, Hef and Harris got back together, marrying on New Years Eve 2012. “I think the center of her life is us, and you can’t ask for more than that,” Hefner told Us Weekly in 2014. “With the age disparity, I’m a very lucky cat. I’m very, very happy.”

He added, “It’s wonderful. It’s better than anything I could possibly imagine. You know, I tried marriage twice before, but there’s no comparison. This is the real deal. And to find true love at this age? It’s remarkable. She’s very special.”

Hugh Hefner died on Wednesday from natural causes. He was 91.

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