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Hugh Hefner Again Set to Marry 'Number One Girl': Sexiest Playboy Cohort?

SodaHead Slideshows 2012/12/03 18:20:53

SLIDESHOW: Sexiest Playboy Cohort?

Kristina and Karissa Shannon
4 of 8

Kristina and Karissa Shannon

Who else but Hef could handle two 20-year-old twins at the same time?
  1. Crystal Harris

    Crystal Harris

    Hef’s former Number One Girl is coming back to the mansion!

  2. Brande Roderick

    Brande Roderick

    Brande has been both a Playboy centerfold and a Baywatch babe.

  3. Kimberley Conrad

    Kimberley Conrad

    Conrad was Playmate of the Year in 1989 – maybe marrying Hef was the prize?

  4. Kristina and Karissa Shannon

    Kristina and Karissa Shannon

    Who else but Hef could handle two 20-year-old twins at the same time?

  5. Izabella St. James

    Izabella St. James

    Izabella is best known for documenting her experiences at the Playboy Mansion in her memoir, titled “Bunny Tales: Behind Closed Doors at the Playboy Mansion.”

  6. Tina Marie Jordan

    Tina Marie Jordan

    When she wasn't busy keeping Hef happy, Tina has co-hosted the radio show “Two Chicks and a Bunny.”

  7. Holly Madison

    Holly Madison

    Madison starred in “The Girls Next Door,” a reality show depicting the lives of three girls at the playboy mansion.

  8. Bridget Marquardt

    Bridget Marquardt

    Along with Kendra Wilkinson, Bridget completed the trio of “The Girls Next Door” stars.

Hugh Hefner Again Set to Marry 'Number One Girl': Sexiest Playboy Cohort?
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Hugh Hefner and his so-called "Number One Girl," Crystal Harris, have announced that they're getting hitched again after she called off a wedding last summer just five days prior.

She may be his "Number One Girl," but does that make the 29-year-old blonde bombshell the sexiest of Hef's extensive list of former paramours? The list includes a plethora of beauties -- in fact, he has been involved with up to seven women at one time.

There's Baywatch alumni Brande Roderick, Playmate of the Year 1989 Kimberley Conrad, and "Two Chicks and a Bunny" radio host Tina Marie Jordan.

We also got up-close-and-personal with Holly Madison and Bridget Marquardt in the series "The Girls Next Door," which later featured twins Kristina and Karissa Shannon, who were just turning twenty years old when they hooked up with the octogenarian and began appearing on the program.

Then there's Izabella St. James, who shared her experiences at the mansion with the world in her memoir, “Bunny Tales: Behind Closed Doors at the Playboy Mansion.”

Click through our slideshow and decide: Who do you think has been the sexiest Playboy love interest?
Add a comment above

Top Opinion

  • .: LiVi :. 2012/12/04 11:07:49
    Holly Madison
    .: LiVi :.
    +9
    Maybe I'm just not shallow enough to understand what is sexy about a bunch of fake, cloned, attention-money-seeking shallow, moronic, self-obsessed whores selling themselves to a creepy, narcissistic, womanising, shallow ugly old man. I cannot find any of them sexy, if they degrade themselves so thoroughly in media and have no self respect or value and security in themselves and have no integrity or individuality. The list could go on forever. I feel sorry for them and wish they could find money and happiness in a different way, that is not a happy or meaningful life.

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Opinions

  • delores.powell.52 2013/01/02 18:01:31
    Holly Madison
    delores.powell.52
    Holly Madison hands down. She is very elegant, not plastic or rubber lol
  • Leslie Goudy 2012/12/13 05:49:31
    Holly Madison
    Leslie Goudy
    Holly has a cute personality
  • Dave 007 2012/12/09 16:25:35
    Bridget Marquardt
    Dave 007
    What happened to the bimbo's from the 60's & 70's? Why aren't any of them on the list?
  • Noor 2012/12/06 17:40:43
    Bridget Marquardt
    Noor
    +1
    They all look like cheap whores to me. I just chose any old name to say that. Who gives a damn what that sick old buzztard is up to any more anyhow? He did amazing damage to the sexuality of America... just put him in a box and hide him from public view with whatever floozy he wants.
  • Black_Rose 2012/12/06 15:02:36
    Holly Madison
    Black_Rose
    I remember when that show 'The GIrls Next Door' was on, and it mostly starred Holly, Bridget, and Kendra. Those three were my favorites. It looked like Holly really did love Hef.

    Bridget and Kendra were my favorites though.

    Girls Next Door
  • Heisenberg 2012/12/05 21:47:51
    Crystal Harris
    Heisenberg
    +1
    Hugh Hefner is just trying to stroke his ego because he's afraid of dying alone.
  • Guest Heisenberg 2012/12/06 12:42:25
    Guest
    +3
    He has surpassed the average life span of your everyday American. Seems he feeds up youth. A forty something woman is way to old for him. Some people froze at the age of 18 and never grow up and with enough money they can still relive their high school sex binges over and over again.
  • Guest Guest 2012/12/06 12:44:34
    Guest
    +2
    meant to say feeds on youth, it's comparable to a vampire but no oldies need apply to have their youth drained out of them.
  • Heisenberg Guest 2012/12/06 18:14:08
    Heisenberg
    He can try to relive his glory days, but nobody can actually buy back his/her youth.
  • Marek 2012/12/05 20:41:51
    Kristina and Karissa Shannon
    Marek
    +2
    I wonder if those whores get enough money for their stint as halfner's bunny.
  • chas 2012/12/05 19:27:08
    Kimberley Conrad
    chas
    One strange octogenarian.
  • dru dixon 2012/12/05 17:45:20
    Crystal Harris
    dru dixon
    +4
    I had to choose one to comment that none of those women with their bleach hair silicone could hold a candle to the playmates of yesteryear! God they all look a like! What happen to redheads and brunetts?
  • Torchy dru dixon 2012/12/06 02:01:35
    Torchy
    Agreed. He throws a brunette in every once in a while, but one can definitely tell that Hef has a type. I like the old Playboy's where the women looked like they wanted to be in the magazine because they felt beautiful, instead of where the women had a ton of plastic surgery and dye jobs to feel beautiful. To each their own, I guess...it's just skin. But the parade of silicone blondes is annoying, and I am a blonde (natural).
  • dru dixon Torchy 2012/12/06 02:03:10
    dru dixon
    +2
    Dorthy Stratton comes to mind. The real innocence and softness of the playmate is gone. These women look hard as nails!
  • Torchy dru dixon 2012/12/06 02:04:57
    Torchy
    +1
    And as tanned as a leather purse!
  • dru dixon Torchy 2012/12/06 02:06:32
    dru dixon
    +2
    LOL! I wondered what was missing! Can we see the girl next door again!
  • Guest dru dixon 2012/12/06 12:46:11
    Guest
    Hefner prefers blonds cause he still does a lot of living in yesterdays.
  • dru dixon Guest 2012/12/06 22:58:03
    dru dixon
    Blondes are fine but can we find some sweet looking young girls like Benton or Stratton? Playboy has really gone down!
  • wow-really 2012/12/05 17:38:13 (edited)
    Holly Madison
    wow-really
    Holly's the only one I've seen, besides Barbie Benton, (who was disqualified by Hef cuz she got too old) who really loved him. Sad they broke up. (Maybe Holly, like Barbie, got too old)
    Sad because she was willing to marry his old, ugly, dried up, egotistical ass, and now to see him so elderly and fragile of mind and body, is just plain sad, really.
    It's also so ironic too.
    Here's a sad,sorry, shallow man who has based his entire love-life according to the age of the woman, (boardering on pedophilia age standards-lol) how they look, and who must be dumb as dirt. Now he is an old man, who seeks to marry a gold-digging whore, (who broke up with him once before cuz HE was "too old", took the ring, and made fool of him in public afterwards) cuz he's so old and desperate, and obviuosly afraid he'll die ALONE, that he is willing to take her back, knowing full well she's an opportunistic, money-hungry beast of burden. And because she had a taste of the real world, and couldn't cut it, wants back to the good life and is willing to kiss his ass until his dying day, which I'm sure she's hoping happens sooner than later..
    Sounds like a match made in heaven.
    They both deserve each other.
    Holly is better off.
  • Guest wow-really 2012/12/06 12:49:10
    Guest
    +1
    He needs youth like a vampire needs blood. Once you are over 40 you are history!
  • Matt 2012/12/05 17:03:16
    Kimberley Conrad
    Matt
  • bill.fleming.77 2012/12/05 15:29:50
    Kimberley Conrad
    bill.fleming.77
    Holly Madison is leading because that is probably the only one most these people on SH know of. It does not even list Barbi Benton his girl friend of 7 years. So I am not sure what else they could be basing this on. She was a bit plastic in personality and did not appear to be to o bright.. Kimberly Conrad is not only beautiful with a beautiful body but she is also the mother of Hef's two boys. She still lives on the compound. These simple truths speaks volumes about this woman and more importantly what she means to Mr. Hefner. The only negative thing I can say about her is that she is a supporter of PETA a cause I believe in but an organization I do not have any respect for.
  • Elizabeth Raggett 2012/12/05 15:04:55
    Kimberley Conrad
    Elizabeth Raggett
    +1
    Kimberly Conrad was gorgeous and she married him at the right time, when he wasn't totally ancient and gross!
  • chas Elizabe... 2012/12/05 19:30:03
  • Elizabe... chas 2012/12/05 19:39:18
    Elizabeth Raggett
    +1
    funny!!!!!!!!!
  • Flowers 2012/12/05 14:16:12
    Bridget Marquardt
    Flowers
    I think Bridget is beautiful all around, she has a sweet personality as well.
  • cindy 2012/12/05 13:31:46
    Holly Madison
    cindy
    +2
    What is wrong with this man ? Crazy
  • JessDeCristo 2012/12/05 12:34:52
    Holly Madison
    JessDeCristo
    Heeeey, he's got the dough, let it roll baby!
  • Torchy 2012/12/05 07:01:03
    Holly Madison
    Torchy
    +4
    She wasn't the brightest bulb; but she was a sweetheart and genuinely seemed to love Hef. I think that makes her the sexiest.

    holly madison pinup
  • Nat™ 2012/12/05 03:46:46
    Holly Madison
    Nat™
    +1
    She's hotter, plus from what I see, she seems to be the only one who really loved Heff.
  • El Prez 2012/12/05 03:26:13
    Crystal Harris
    El Prez
    +2
    wHO CAN TELL THEM APART? and wHO CARES?
  • adeenmckenziekennedy 2012/12/05 02:56:59
    Holly Madison
    adeenmckenziekennedy
    I like Holly better.
  • BigD_U.S.M."HD"Vet. 2012/12/05 02:50:28
    Kristina and Karissa Shannon
    BigD_U.S.M."HD"Vet.
    Why?
  • thomas.krovn 2012/12/05 01:33:09
  • nicesteve 2012/12/05 00:33:16
    Bridget Marquardt
    nicesteve
    Not all Playboy Playmates are THAT naughty. Several of them are somewhat nice.
    Just all of the ones listed above are really naughty. And that brat Bridget Marquardt
    is the naughtiest of the lot. Actually, phlebotomists (aka vampires), hair stylists, and
    school teachers are naughtier than a lot of playboy playmates. Come to think it, I
    sure hope that a phlebotomist never makes it into the centerfold of Playboy. Or worse
    still, becomes a Playboy Playmate of the year. She would be as dangerous and as
    terrorfying as she's beautiful.
  • trollatc 2012/12/05 00:11:19
    Holly Madison
    trollatc
    There are others I would vote for. But Holly is near the top of the list.
  • dzzshadz 2012/12/04 21:55:32 (edited)
    Holly Madison
    dzzshadz
    +1
    She is just the best of the choices given. Barbie Benton is sexiest.
  • moiraregis 2012/12/04 21:29:52
    Crystal Harris
    moiraregis
    i wanted to pick them all, but sodahead wouldn't let me; w/o even looking, i have a feeling they're all interchangeably blonde, big-titted, long-legged, gorgeous; i have no idea what kind of person each one is and don't really care. i hope each of them got a nice settlement when hef moved on. if it makes an old man happy, and no one else gets hurt, mazel tov to all--
  • ACT17 2012/12/04 20:29:49
    Holly Madison
    ACT17
    I don't necessarily think she's the sexist, but i loved her and hef.
  • Robert Strobel 2012/12/04 19:54:53
    Kristina and Karissa Shannon
    Robert Strobel
    Two is always better than one.

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