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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On Bitter Celebrity Custody Battles...ddfstop said "Children always suffer when their adults start acting like "children!" Tax Evation?? That woman is a fine role model for her daughter ... not! She should never be allowed to have any custody of their daughter because the daughter will only get bounced back to Jesse and Sandra the next time she decides to mess with the IRS. Even a genius will testify that that is not very smart ... forget being a genious. It ain't nice ta mess wit da IRS!!'Nuff said!"
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On Celebrity Playboy Covers ...bhig bhil said "I was watching Young Frankenstien, when we thought about Terri Garr and then Bernadette Peters, as comedieenes. Then I wondered what happened to Bernadette? Well, I have found out that she is well and is still a hottie at 61. My God The Woman Looks Good! Her and Andie MacDowell have that Hair, that beautiful frizzy wonderful Hair! Go Girl"
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On "Celebrity Apprentice" Applicants' Job Qualifications...judykk334 said " I found a great dating site________ W e a l t h y O n l y. c o m ________. The best dating club for seeking the rich singles, sexy beauties. What's the most important is that you don't have to be a millionaire, but you can meet one. BTW, Charlie Sheen found his true love on that site in 2007."
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Comments
hibye
June 29, 2009 - 06:08 AM GMT
Hugh, I hope you spent more money this time on them and bought some that are of a better class than skanky Kendra.
spacemanjack
June 29, 2009 - 05:45 AM GMT
In the pic with Barbi Benton, anyone else a little creeped out that he looks so much like Bono (Vox) there? http://www.enciclopedia.com.pt/images/bonovox.jpg
Guess we know what Bono's going to look like in 30 years.
PhilipLQ
June 29, 2009 - 05:15 AM GMT
"A man that old doesn't get chicks like that?" Get a life, losers. Guess what, I'm 60 yrs old, not a rich man at all, and I'm dating a beautiful, intelligent and witty 21 yr old woman who wants to marry me. You are as young as you feel, not as old as you look.
linux1g
June 29, 2009 - 03:43 AM GMT
'Big difference between all these negative comments and the man himself - he has 'em, you don't - quit yer bitchin'! Hey Heff, thanks for bringing so much T & A to the average American male for all these years!.
bits
June 28, 2009 - 11:19 PM GMT
Bet he can't get it up.
Flatpik
June 28, 2009 - 11:16 PM GMT
So women like high achieving guys with money -wow, there's a newsflash! Any of you miserable whining losers start a billion dollar enterprise? Hefner is smart and classy. Happy for him he has such nice companionship.
I've found that you can tell a lot about the boss by the way a business treats its vendors. I had the opportunity to business with Playboy Magazine during the 80's and everyone I dealt with at the company was courteous, professional and in all ways a pleasure to do business with. I have no doubt this culture came from Hefner.
desertdog
June 28, 2009 - 10:39 PM GMT
What a bunch of up-tight do-gooder losers these previous comments came from!!!!! Personally,I like brunettes and if I could I'd have a mansion full of naked ones running around as well. GO HEF!!!!! Shakira for President!!!!
Biker at Bad Bobs, Robert, Louisiana
June 28, 2009 - 10:22 PM GMT
He's a pussy...
Biker at Bad Bobs, Robert, Louisiana
June 28, 2009 - 10:21 PM GMT
Yeah, Old Hefner..He buys them, but what plastics they are.. A shallow man and his shallow women... I wouldn't spend my time with someone of no personality. You would never ever see a classy woman with Hugh... Just these things, these things that have no life in them... He must be an extremely dull man too. And what does he stand for anyway ? A man wearing pajamas, hanging out with whores. Real men do not want unreal women. Hugh is just a fucking pussy..
Biker at Bad Bobs Bar, Robert, Louisiana
Biker at Bad Bobs, Robert, Louisiana
June 28, 2009 - 10:17 PM GMT
Yeah, Old Hefner..He buys them, but what plastics they are.. A shallow man and his shallow women... I wouldn't spend my time with someone of no personality. You would never ever see a classy woman with Hugh... Just these things, these things that have no life in them... He must be an extremely dull man too. And what does he stand for anyway ? A man wearing pajamas, hanging out with whores. Real men do not want unreal women. Hugh is just a fucking pussy..
Biker at Bad Bobs Bar, Robert, Louisiana