Hugh Hefner and his girlfriends, 2009
Hugh Hefner and Barbi Benton, 1973
Sondra Theodore and Hugh Hefner, 1977
Shannon Tweed and Hugh Hefner, 1983
Hugh Hefner and Carrie Leigh, mid-'80s
Kimberly Conrad, Hugh Hefner, and their sons, 1998
Brande Roderick and Hugh Hefner, 2001
Tina Jordan and Hugh Hefner, 2002 
Hugh Hefner and the Girls Next Door, 2007
Hef's Girlfriends | 1 of 9
Michael Bezjian/WireImage
Crystal Harris, Hugh Hefner, Karissa Shannon, and Kristina Shannon, May 16, 2009
Think you can do better? Respond with your own gallery now!Hef's Girlfriends
Hugh Hefner and his girlfriends
We get that they're twins, but we were still a little bummed out to hear that Hugh Hefner can't tell two of his three girlfriends apart. Honestly, if you look quickly at a photo of Hef's latest batch of ladies, it's even a bit hard to distinguish 22-year-old Crystal Harris from the 19-year-old Shannon sisters. But luckily for Hef, either Karissa or Kristina has a small mark on her neck that helps him crack the bombshell code.
Do they really look that much alike? Or is the world's most legendary bachelor just getting that old? Maybe it's the age difference; we know we can't always tell friends' babies apart, and there's a much shorter time span between us and newborns and Hef and his babes.
Then again, maybe Hef's still pining away for his former steadies, "The Girls Next Door": Holly Madison, Bridget Marquardt, and Kendra Wilkinson. The trio left the Playboy Mansion last year. But at age 83, Hef has shown us time and time again that he's good at loving the ladies and then moving on. Take a look at some of the women he's wooed over the years.
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Comments
kanata
October 26, 2009 - 09:37 PM GMT
You know what is even funnier and more pathetic than the ones talking about him going to hell? Is all of you on here, judging, and running down others for doing just THAT, judging and running people down.
Never ceases to amaze me how many people will get on their horse and rant and complain committing the very same act of wrong you are yelling at the others for. Which in turn makes you not only as much or MORE of a hypocrite than they are, but also makes ya look rather ignorant and stupid.
If you honestly want someone to take what you say seriously, or even so much as bother to read any of your posts after seeing such ignorance, you might want to approach the subject with a little more tact and class, and NOT stoop to the very level of the ones you are pointing at. Just remember for every finger you point, there are always going to be three more pointing back at you.
So either you are young, immature, and don't really belong on boards that hold adult content, or you are single minded and silly to think anyone would not see that you are committing the very crime you are accusing others of.
And considering you can't seem to make your point without using unintelligent, foul mouthed, disgusting language, I suspect no one DOES take anything you have to say seriously, and skips over ever other post you have because they don't want to waste their time on such imbecilic behavior.
And for those of you who do not agree with this mans lifestyle, and sit here writing about how he is going to hell? If you don't like it? DON'T READ IT!!! Go find a site you can handle looking at, or skip to the content you DO approve of. If you seriously think anyone is going to take what you say to heart, or think that Mr Hefner even BOTHERS to read these boards and commentaries, let alone take anything your opinionated righteous drivel says to be any kind of truth, and suddenly rush to the nearest church to confess his 80+ yrs of fun and leisure to be unholy, you too are sadly misdirected. Even if you stood outside his door with a bullhorn, that life of fun has made him millions, and allowed him a lifestyle no one else on earth can say they have, he'd laugh you all the way to the pearly gates and tell you not to let them hit you in the ass on the way in! He doesn't care! You are wasting your time, and really need to go elsewhere if you truly think you are going to make any kind of difference in someones life, because I can re assure you, that anyone who comes to read these pages, has NO interest in what you have to say and you are actually doing more of a dis service to God than spread his word. People see you do that kind of thing on places like this just makes them harder and colder towards EVER being capable of opening their hearts to hear it.
Why not work on those around you first, I am positive you know plenty who could use it. And if you are a TRUE believer? You are not so naive to think you are truly any better than any of these people. Any true man of God, always will admit that they themselves need just as much if not more work than the people you attempt to judge. And second it is not your place to judge, something else you should know as a believer. There is only ONE person allowed to do so in most religions, and any one of us on earth are NOT it.
So mind your own house of cards before they crumble beneath you, and should that actually happen? Maybe think back to all this spewing and judging you are doing, it should give you a good clue as to why.
I don't remember the exact quote but I do know there is reference in the bible about the person who has the gall to judge another, is more sinful than the sinner they accuse.
manda22
July 21, 2009 - 08:28 AM GMT
By the way Hugh is such sweet guy. and for real though You people who say " if he doesn't change is ways he's going to hell" YOU REALLY ARE PATHETIC!
lilblackkitten
July 13, 2009 - 04:31 AM GMT
I hate to say it but, for you boys out there if, it wasn't for Hef most of you wouldn't even know what the difference is between real and fake anything.
This man gave us the first centerfold and taught lots of MEN what a real woman wants in a man.
MR G
July 12, 2009 - 06:35 PM GMT
he gets more a$$ than a toilet seat
MR G.
Somechick
July 12, 2009 - 06:07 PM GMT
PhilipLQ: She wants your money. Plain and simple.
redhotmodel
July 12, 2009 - 05:39 PM GMT
OMG!! What is wrong with you people? Hef has the best life that anyone can imagine. I love Playboy! The articles are great. He can have any woman he wants. I would love to see more red heads though! I think red heads are very beautiful, unique, sensual, seductive and erotic.
Desmond V Crotty Jr
July 12, 2009 - 04:02 PM GMT
For JoGolf there, I ask you this;
WHO BUYS PLAYBOY TO READ THE ARTICLES???????
manda22
July 05, 2009 - 04:49 AM GMT
Hugh Hefner is a great guy and for you all to judge him is f***ing pathetic. and for mlynch481 to say that it's a real shame about the sin and fornication Hugh has committed over the years and that if he doesn't change his ways he's going to hell. WTF gives you the right to say shit like that and judge somebody like that? Your PATHETIC! why don't you worry about your on life and stop saying rude shit about other people
sagerat
June 30, 2009 - 04:12 PM GMT
i find it amusing that holly madison who only wanted "marrige and children" is showing herself to be a golddigging tabloid queen when "wild" kendra wilkensen is married and pregnant mr hefner is for sure better off without the woman he thought was the love of his life if her actions now speak true about her
tony123456123
June 30, 2009 - 02:29 PM GMT
I don't believe that girls are everything in the world. Although it is tempting. True love maybe he has known it or not we should not be the ones to judge.