Here are the 5 hottest Hugh Hefner girlfriends. Many of Hef’s girlfriends look quite a bit a like, but some stand out and the crème rises to the top! From the girl-next-door, to the brunette stunner, to the law school grad, to the one put a ring on, Hef’s babes have been impressive to say the least! They’re all special in their own way, but it takes a special girl to be one of the hottest Hugh Hefner girlfriends!
- Holly Madison. One of the "Girls Next Door" on Bravo’s popular series, Holly Madison was Hef's girlfriend for seven years and the number one girl in Hef’s life for six of them. One of Hef’s most ambitious ladies, Holly produced "Playboy" pictorials in the last several years of her relationship with Hef and began carving out a career for herself. Holly’s girl-next-door personality, ambition and devotion to Hef make her one of the hottest Hugh Hefner girlfriends.
- Barbi Benton. As Hugh Hefner’s first girlfriend, Barbi makes the list as one of the hottest Hugh Hefner girlfriends. Known as one of the quintessential "Playboy" models, Barbi is in the minority of girlfriends as being one of the only brunettes in the bunch.
- Brande Roderick. Both a "Baywatch" babe and a "Playboy" centerfold, Brande’s list of credentials lands her as one of the hottest Hugh Hefner girlfriends. Brande’s signature blonde locks, sparkly baby blues and sweet disposition make her a classic Hefner lady.
- Kimberly Conrad. No one can argue this lady’s pedigree from Playmate to Playmate of the Year to girlfriend to wife in a year and a half flat! It’s Kimberly’s determination, as well as her all-American good looks, that make her one of the hottest Hugh Hefner girlfriends.
- Izabella St. James. This is no dumb blonde here. As a law school grad, Izabella is not only one of the hottest Hugh Hefner girlfriends, she’s also one of the brainiest!
What Others Are Reading Right Now.
15 Shirts Women Simply Can’t Resist—and Why
From Ts to button-downs and beyond, these must-haves will get her everlovin’ attention.
As Boogie Nights Turns 20, Here’s What You Didn’t Kno...
Fun facts about Paul Thomas Anderson, Dirk Diggler, Rollergirl and more.
19 Men’s Grooming Gaffes That Totally Turn Women Off
And what to do about them.