Losing a cultural icon (not to mention general badass and amazing businessman) is never easy - and it's in times like these we like to reflect on the legacy leftover. Hugh Hefner needs no introduction or biography, so we thought we'd reflect on his wives and a few of the other women in his exciting life that he loved. So let's start at the beginning - first, there was...

Millie Williams

... who Hugh met at Northwestern and fathered his first two children with. Then, 30 years later, came: 

Kimberley Conrad 


Gorgeous mother to Cooper and Marston Hefner. As most of you know, Cooper is now the Chief Creative Officer at Playboy. Last but certainly not least: 

Crystal Harris Hefner  


Movie night with @crystalhefner. Tonight's Mansion movie is "Harvey." #playboymansion #easterweekend

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Crystal was on The Girls Next Door before marrying Hugh, and was with him until he passed. 

He had several notable girlfriends, too, many of which have made our site. Eh hem: 

Barbi Benton


Kristina and Karissa Shannon - not the first twins Hef dated


Kendra Wilkinson, Holly Madison, and Bridget Marquardt


RIP, Hugh Hefner - thank you for your lasting legacy!