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 💔."
— Bridget Marquardt (@Bridget) September 28, 2017
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.
Goodbye #Hef Mr Hefner I have so many thoughts, I have no brain n right now to edit 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. You gave me my life... People tell me all the time That I was your favorite... I'm in such deep shock. But you were old, your back hurt you so much. Last time I saw you You were using a walker. You didn't want me to see. You couldn't hear. You had a piece of paper in your pocket you showed me - with my name Pamela with a heart around it. Now, I'm falling apart. This feeling is so crazy. It's raining in Paris now. I'm by the window. Everything anyone loves about me is because you understood me. Accepted me and encouraged me to be myself. Love like no one else. Live recklessly With unfiltered abandon. You said the magazine was about a girl like me. That I embody the spirit you fantasized about. I was the one. You said. I can hear you say - Be brave. There are no rules. Live your life I'm proud of you. There are no mistakes. And with men - Enjoy ... (Your wonderful laugh) You have the world by the tail You are a good girl And you are so loved - You are not crazy. You are wild and free Stay strong, Stay vulnerable. ... "It's movie time" You loved my boys ... You were always, always there for us. With your love Your crazy wisdom. I will miss your everything. Thank you for making the world a better place. A freeer and sexier place. You were a gentleman charming, elegant, chivalrous And so much fun. Goodbye Hef ... Your Pamela 💋
"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:
RIP to the legendary Hugh Hefner! I'm so honored to have been a part of the Playboy team! You will be greatly missed! Love you Hef! Xoxo— Kim Kardashian West (@KimKardashian) September 28, 2017
Family friend Paris Hilton shared her sadness over his death on Facebook:
Others followed suit, including former Playboy model Carmen Electra:
R.I.P. Hugh Hefner 😥 The American Icon who in 1953 introduced the world 2 Playboy mag and built the company into one of the most recognizable American Global brands in history , I am so grateful I had the opportunity to shoot many Playboy celebrity pictorials with u Hef❤️ thank u for picking me and Bringing me into the magical world of Playboy ! I just can't stop crying and I can't imagine how many bunnies are crying for u too. U are a class act and I will always have gratitude for your kindness 🙏🏼love u Hef #hughhefner #playboy #icon @playboy
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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