Top 5 Hugh Hefner Girlfriends

By Sean Percival on November 5th, 2008

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A man among men, Hugh Hefner is well known for his breakthrough publication, Playboy. Hefner is also well known for something else: his proclivity towards women. In fact, over the years, the objects of Hefner’s affection have become the inspiration for rumors, gossip and even admiration.

While Hefner has only been married twice (and is still technically married), he has had many women who he has claimed as his girlfriends over the years.

Counting his wives, the un-official list of Hefner’s gals numbers around 16 or so, give or take a few depending on what list you go by. Sorting through this group of beauties can be a daunting task, but we accepted the challenge so that we could bring you the following list of Hugh Hefner’s top girlfriends.

#5 Lillian Muller

Muller is a Norwegian model who made Playmate of the Month in August 1975 and went on to become Playmate of the Year in 1976. No question why Hefner picked this one for his collection and why we’ve picked her for inclusion in our top 5.

#4 Bridget Marquadt

Despite the French name, Marquadt hails from Tillamook, Oregon. She’s one of Hef’s most recent catches, although she just left the mansion for greener pastures. She has starred in the Playboy production “The Girls Next Door” since 2005.

#3 Holly Madison

Holly Madison is another American beauty that comes from Oregon. Hey, maybe there’s something to this trend? In any event, Holly also starred in the “The Girls Next Door”, but also left the love triangle between herself, Hefner and Bridget Marquadt earlier this summer.

#2 Barbi Benton

Benton met Hefner in 1968 when she appeared on his show “Playboy After Dark”. She appeared on several Playboy Magazine covers, although she was never a Playboy Playmate, just an entertainer who ended up as the girlfriend of the boss.

#1 Kimberley Conrad

Kimberley Conrad, Hefner’s second and still current wife, was Playmate of the month in January 1988 and Playmate of the Year in 1989. The couple married in 1989 and were together for 10 years until an amicable separation. She is the mother of Hefner’s two sons. So why did I rank her as the #1 Hefner gal of all time? Not only did she manage to marry him, she is still legally married to him, despite the separation and myriad of other women. Now that is a spectacular achievement!