Before we begin, let’s all take a moment of silence to remember the Greatness that is Hugh Hefner.
On Sept 27, 2017 one of the most iconic men in history passed away at the age of 91. Hugh Hefner, the man that brought us Playboy, lived a life that most men could only dream of.
His legacy started after quitting his job as a copywriter for Esquire. From there, he ventured out on his own and procured enough investment to launch Playboy. At that time, it was called Stag Party.
Credits NY Daily News
The very first issue was published in December 1953 and featured Marilyn Monroe in a nude calendar shoot. It sold over 50,000 copies. With the release of Stag Party, Hugh Hefner had disrupted social norms with his controversial idea.
On June 4, 1963, Hefner was arrested for promoting obscene literature after an issue of Playboy that featured nude shots of Jayne Mansfield was published. The case went to trial and resulted in a hung jury. I know what you are probably thinking, this man is a bad ass.
Hugh Hefner’s ventures also included Playboy’s Penthouse and Playboy After Dark. His glorious lifestyle was promoted through his magazines as well as his T.V. shows, but in 1985 at the age of 59, Hugh suffered a minor stroke which led him to re-evaluate his life. Afterwards, in 1988, his daughter Christie took over Playboy, however Hugh Hefner would remain the face of the empire.
Credits Daily Mail
1971, Hefner purchased a second residence in Los Angeles known as Playboy Mansion West for $1.1 million and in 1975, he moved there permanently from Chicago.
The Mansion is known for its extravagant and wild parties. The Playboy mansion is purely a man’s fantasy materialized. With bare naked women everywhere and plenty of celebrity faces, one could only dream of what it must be like to be a part of it all.
In 2016, the Playboy Mansion was sold to Daren Metropoulos, a principal at private equity firm Metropoulos & Company, for $100 million.
Crystal Harris – Hugh Hefner dated Crystal Harris on-and-off since 2008. The couple tied the knot in 2012.
Anna Sophia Berglund – Hugh Hefner was involved with Anna Sophia Berglund in 2011.
Jenna Bentley – Hugh Hefner was reportedly hooking up with Jenna Bentley in 2009.
Kristina Shannon – Hugh Hefner was romantically involved with Kristina Shannon from 2008 – 2010.
Holly Madison – Holly Madison was one of Hugh Hefner’s girlfriends from 2001 – 2008.
Kendra Wilkinson – Kendra Wilkinson was in a relationship with Hugh Hefner from 2004 – 2008.
Bridget Marquardt – Hugh Hefner counted Bridget Marquardt as one of his girlfriends from 2002 – 2008.
Brande Roderick – Hugh Hefner hooked-up with Brande Roderick from 1999 – 2000.
Kimberley Conrad – Hugh Hefner was married to Kimberley Conrad from 1989 – 2010.
Shannon Tweed – Shannon Tweed was reportedly one of Hugh Hefner’s girlfriends from 1981 – 1983.
Sheila Levell – Shelia Levell was one rumored to be one of Hugh Hefner’s regular hook-ups from 2003 – 2004.
Melissa Dawn Taylor – Hugh Hefner was romantically involved with Melissa Dawn Taylor from 2008 – 2009.
Dasha Astafieva – Hugh Hefner was rumored to be romantically involved with Dasha Astafieva around 2008.
Izabella St. James – Hugh Hefner was reportedly hooking-up with Izabella St. James from 2002 – 2004.
Lana Kinnear – Hugh Hefner reportedly hooked-up with Lana Kinnear from 2002 – 2004.
Zoe Paul – Hugh Hefner was reportedly romantically involved with Zoe Paul from 2002 – 2004.
Janine Habeck – Janine Habeck was rumored to have hooked-up with Hugh Hefner in 2006.
Stacy Burke – Hugh Hefner reportedly had a fling with Stacy Burke in 2002.
Teri Harrison – Teri Harrison also reportedly hooked-up with Hugh Hefner in 2002.
Cristal Camden – Hugh Hefner was rumored to be romantically involved with Cristal Camden from 2001 – 2003.
Tiffany Holiday – Hugh Hefner was reportedly hooking up with Tiffany Holiday from 2001 – 2003.
*As I write this article and note how many women Hugh Hefner has been with… I came to the crazy realization that this list could go on for a few days… So I’m just going to leave it at 21 girls… If you guys are really interested, here’s a good start:
Hugh Hefner’s girls