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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