But one area in Hef's wheelhouse that's often overlooked is the mark he left on reality television, specifically, the E! series "The Girls Next Door."
The TV series originally aired from 2005 until 2010, and was co-created by the Playboy founder.
The first five seasons starred Hef's three main girlfriends, Holly Madison, Kendra Wilkinson, and Bridget Marquardt, while the sixth and final season focused on Hef's new girlfriends, twins Kristina and Karissa Shannon, and a then-23-year-old Crystal Harris, who would eventually become his third wife.
On Thursday, both Wilkinson and Marquardt posted reactions to their ex-boyfriend's death.
Via Twitter, Marquardt posted a picture of her and Hef in better times, writing, "So sad but forever grateful for all the wonderful memories and amazing experiences #RIPHef #Playboy 💔."
In a statement, Wilkinson said: "Hef changed my life. 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."
As of press time, Madison has yet to post a reaction on her social media channels or through a statement, however, in her 2015 memoir Down the Rabbit Hole, the "Holly's World" star criticized Hefner's treatment towards her and his other girlfriends, claiming that all the girlfriends were expected to sleep with the Playboy founder and that he would pit them against each other.
Despite these allegations, many of Hef's ex-girlfriends, friends, and Playmates shared their condolences on social media.
Pamela Anderson, who made the cover of Playboy a whopping 14 times, shared her grief on Instagram, posting a video of her crying and whispering, "Goodbye, Hef," along with a poem about her love and respect for her friend.
"Outside of my family, you were the most important person in my life. You gave me my life... People tell me all the time that I was your favourite," Anderson wrote.
"Everything anyone loves about me is because you understood me. Accepted me and encouraged me to be myself," she added.
Kim Kardashian, who appeared on the cover of Playboy in 2007, also spoke out on Hefner's death, writing on Twitter:
Family friend Paris Hilton shared her sadness over his death on Facebook:
Others followed suit, including former Playboy model Carmen Electra:
And Jenny McCarthy:
As of press time, Hefner's wife, Crystal Hefner, has yet to make a statement about her husband's death.
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