Hugh Hefner passed away yesterday at 91 years old.

With a lifetime full of accomplishments, fame, friends and success, it's no surprise so many people have expressed their sadness regarding the Playboy mogul's death—especially the women he employed and worked with over the years.

However, while there were plenty of Playboy bunnies, platinum blondes and models who came in and out of Hefner's life (not to mention, the mansion), there were a select few who were just a little extra special to him.

Hefner was married three times, and though you may not agree with it, he also had several long-term partners who he considered very important women to him, even if he was dating other people at the same time.

Scroll below to see which ladies reigned supreme in the late Playboy mogul's life:

Hugh Hefner, Crystal Harris

Ethan Miller/WireImage

Hugh Hefner, Kimberley Conrad

Laura Luongo/

Christie Hefner, Millie Gunn, Kimberley Conrad, Hugh Hefner

Steve Liss/The LIFE Images Collection/Getty Images

Hugh Hefner, Christie Hefner

Ron Galella/WireImage

Marilyn Monroe, Hugh Hefner

Getty Images

Hugh Hefner, Pamela Anderson

Theo Wargo/WireImage

Kendra Wilkinson-Baskett, Hugh Hefner

Denise Truscello/Getty Images

Holly Madison, Hugh Hefner

Ethan Miller/Getty Images for BASE Entertainment

Hugh Hefner, Bridget Marquardt

Jean Baptiste Lacroix/WireImage

Hugh Hefner, Barbi Benton

AP Photo/Bob Dear

Hugh Hefner, Mary OConnor

Denise Truscello/WireImage; E!

Meanwhile, on Wednesday evening, Playboy announced that Hefner had passed away from natural causes at the Playboy Mansion. 

"My father lived an exceptional and impactful life as a media and cultural pioneer and a leading voice behind some of the most significant social and cultural movements of our time in advocating free speech, civil rights and sexual freedom," his youngest son, Cooper Hefner, shared in a statement. "He defined a lifestyle and ethos that lie at the heart of the Playboy brand, one of the most recognizable and enduring in history."

Cooper continued, "He will be greatly missed by many, including his wife Crystal, my sister Christie and my brothers David and Marston, and all of us at Playboy Enterprises."

Information regarding memorial services are not available at this time.

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