Hugh Hefner has been in the news a lot lately.  First, it was for rumors that 2 of his “girlfriends” left him for other celebrities - Kendra for Eagles receiver Hank Baskett and Holly for illusionist douche Criss Angel.  This week, the story is that he’s facing bankruptcy.  Regardless of what people are saying, when you’ve lived a life like him, nothing else matters.

For all we know, Hugh rivals Wilt Chamberlain in the gettin-it department.  Below are the ladies that he’s called his girlfriend at one point or another.  They’re usually Playmates of the Year, but sometimes he settles for actresses, hoochies, foreigners, or even wives.

Playmates of the Year

Donna Michelle:

SEE THE REST AFTER THE JUMP…

Marilyn Cole:

Lillian Muller:

Hefner did admit to dabbling in bisexuality, and tranny-like Muller might have inspired it.

Patti McGuire:


Shannon Tweed:

Brande Roderick:

Not sure why Hugh got rid of Brande and her Marissa Miller-like looks

Wives
Mildred Williams:


OK so this isn’t the Mildred Williams that was Hefner’s first wife, but it is the only Mildred Williams I could find.

Kimberley Conrad (also a PMOY and still technically married):

Actresses
Carrie Leigh:

(update) Barbi Benton:

Most people don’t know that Benton was never a Playmate, just an entertainer that happened to be on the cover a few times.

Reality Show Hoochies
Holly Madison:

Bridget Marquadt:

Kendra Wilkinson:

See more recent shots of Kendra here.

The Rumored New Girl
Dasha Astafieva:

Not bad, Hugh.  Not bad.  If you really are bankrupt, just write a memoir and you should be set.

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