Hugh Hefner Dead at 91: Relive the Legendary Playboy Founder’s Life in Pictures

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Hugh Hefner Dead at 91: Relive the Legendary Playboy Founder's Life in Pictures

The world lost a pop culture icon when Hugh Hefner, the iconic founder of Playboy, died on Wednesday, September 27. The legendary magazine publisher was 91, and left behind quite a legacy.

He was born Hugh Marston Hefner on April 9, 1926, in Chicago, and was the oldest of two boys born to Grace and Glenn Hefner. The publisher graduated high school in 1944 and founded Playboy in 1953, which he turned it into a world-renowned brand and empire. The businessman is survived by his wife, Crystal Harris, sons Cooper, 26, Marston, 27, and David, 62, and daughter Christie, 64.

Scroll down to take a look back at Hugh Hefner’s iconic life and career in photos.

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Hugh Hefner Dead at 91: Relive the Legendary Playboy Founder's Life in Pictures

The world lost a pop culture icon when Hugh Hefner, the iconic founder of Playboy, died on Wednesday, September 27. The legendary magazine publisher was 91, and left behind quite a legacy.

He was born Hugh Marston Hefner on April 9, 1926, in Chicago, and was the oldest of two boys born to Grace and Glenn Hefner. The publisher graduated high school in 1944 and founded Playboy in 1953, which he turned it into a world-renowned brand and empire. The businessman is survived by his wife, Crystal Harris, sons Cooper, 26, Marston, 27, and David, 62, and daughter Christie, 64.

Scroll down to take a look back at Hugh Hefner’s iconic life and career in photos.

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First Love

Hefner married his childhood sweetheart, Mildred "Millie" Williams in 1949 after his time in the army. They welcomed daughter Christie in 1952 and son David in 1955. The couple divorced after 10 years of marriage, and his famous bachelor life began.

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The Magazine

Hefner helped revolutionize publishing and welcomed a new era of sexual revolution in magazines when he started Playboy in 1953. The magazine became one of the most controversial magazines in history for its risqué content and frequent use of nudity.

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Playboy Bunnies

After his split from his first wife, Millie Williams, the magazine editor had a relationship with girlfriend Barbi Benton and also dated several other Playboy models throughout the majority of his life. 

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The Mansion

In 1971, Hefner purchased the now-iconic Playboy Mansion in Los Angeles. The notorious 22-room house became widely known for the massive parties he used to throw there in the 1970s. 

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Wedding Bells

The reality star married his second wife, Kimberley Conrad, in 1989, and they had sons Marston and Cooper. The couple separated in 1998 and the Playmate of the Year 1989 moved into a home next to the Playboy Mansion. They didn’t officially divorce until 11 years later in 2010.

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Dance With My Father

Hefner danced with his firstborn, Christie, who is also the former chairperson and chief executive officer of Playboy Enterprises, at her wedding to lawyer Bill Marovitz in 1995.  

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Hollywood Star

Hefner was a staple in pop culture, often making cameo appearances on TV shows and in movies. He guest-starred in projects such as The Fresh Prince of Bel-Air, The House Bunny and The Apprentice.  

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His Favorite

Hefner often remained close to his past girlfriends and the models who’ve appeared in the pages of Playboy, including Pamela Anderson. After his passing, the actress posted a tearful video on Instagram, on Thursday, September 28: “I am me because of you. You taught me everything important about freedom and respect. Outside of my family, you were the most important person in my life.”

She added: "You gave me my life. People tell me all the time that I was your favorite. I'm in such deep shock."

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The Girls Next Door

Holly Madison, Kendra Wilkinson and Bridget Marquardt moved into the mansion in 2004, and in 2005 they started filming their E! reality show, The Girls Next Door, about their lives as Hefner’s girlfriends. 

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No. 1 Girlfriend

Madison and Hefner split in 2008 after five years together, and all three girls from The Girls Next Door left the mansion. Madison went on to star in her own spinoff series, Holly's World. She also wrote a tell-all memoir, titled Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny, about her life with the Playboy mogul.

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Kendra on Top

Wilkinson maintained a tight bond with Hefner after leaving the mansion and even married Hank Baskett in 2009 at the house, which was featured on her own spinoff show, Kendra on Top. "Hef changed my life," the Playboy model, 32, told Us Weekly in a statement after his passing. "He made me the person I am today. I couldn't be more thankful for our friendship and our time together. I will miss him so much but he will be in my heart forever." 

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Casablanca

Hefner had a timeless birthday tradition through the years. To celebrate his April 9 birthday, the Playboy founder hosted a Casablanca-themed bash for his family and friends every year.

“Casablanca is my all time favorite film and we watch that movie and then gather in the dining room, which we have transformed into Rick's Café Américain and we have Champagne and caviar by candlelight,” Hugh told Us in 2011 of the tradition. “It's a very romantic evening. Everyone dresses up in the style of the 1940s, similar to the movie.”

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Still Present

Hefner continued to make appearances at Playboy events, including the Playboy's 2013 Playmate Of The Year luncheon, with his youngest son, Cooper, in May 2013. 

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Forever Love

The Playboy mogul proposed to girlfriend Crystal Harris on Christmas Eve 2010, and the pair went on to tie the knot on New Year’s Eve 2012. Their nuptials came after Harris’ controversial decision to call off their wedding in June 2011, just five days prior to their big day.

“I tried marriage twice before but there's no comparison,” Hugh told Us Weekly in 2014 of his marriage to Harris, who was 60 years younger. “This is the real deal. And to find true love at this age? It's remarkable.”

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A Legacy

Not only did Hefner create an empire with Playboy, but he also used his fame and fortune for the good of the community. He was known for his humanitarian and charity work through the years, helping restore the iconic Hollywood sign twice, and donated millions of dollars to the UCLA Film & Television Archive and the USC School of Cinematic Arts.