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Heirs To The Hefner Crown: Hollywood Stars Who Have Lived The Playboy Dream

October 10th, 2008 10:54am EDT
Hugh HefnerA dark cloud loomed over the Playboy Mansion. Hugh Hefner was dumped by not one but three babes simultaneously. Before you drown your all-my-heroes-are-geezers sorrows in Chivas and Cuban cigars, remember: You should never doubt Hef. He’s already frolicking with three new blondes (two of them twins) in the grotto. But it does make us wonder. Is it time for Hef to pass on his proverbial baton to some other stud? (Check out a video HERE!)

People who only know him as the 82-year-old guy on The Girls Next Door must find it hard to believe that he set the standard for all of the commitment-phobe celebrities who would follow in his footsteps. But these guys owe it all to Hef.


WARREN BEATTY

In his day Warren was the hottest guy around. He dated everyone from Jackie Kennedy to Madonna. Then he met Annette Bening and settled down. It’s hard to believe this consummate ladies' man has been off the market for 16 years.

WARREN BEATTY



JACK NICHOLSON

Jack proved it wasn’t about looks; it was about style. He was married once, from 1962 to 1968, and spent 17 years with Anjelica Huston. But that doesn’t make him any less of a dog. And even though he’s no longer a young stud, the 71-year-old holds his own. Let’s not forget he was going out with the much younger and hotter 29-year-old Lara Flynn Boyle when he was 62.

JACK NICHOLSON



BRAD PITT

Sure, Brad might be the world’s ideal husband and dad these days, but before that he went through a long list of starlets, including Robin Givens, Juliette Lewis, and Gwyneth Paltrow, showing he had a wide range of tastes in Hollywood babes.

BRAD PITT



GEORGE CLOONEY

Unlike his buddy, Brad, the once-married Clooney has vowed to stay single from here on out. And he’s good at it, mixing it up in celebrity flings with Lucy Liu and Teri Hatcher between long-term stints with up-and-comers like Krista Allen and Sarah Lawson. Plus, he spends most of the time in his Italian villa, so he can kind of keep it all to himself.

GEORGE CLOONEY



SCOTT BAIO

Before he was "46…And Pregnant," Baio was almost as big a playboy as Hef. The serial dater had to have a life coach and a reality show to help him figure out that jumping from girl to girl isn't necessarily the way to go. But, in fairness, it must be a hard choice to make when your exes include Denise Richards, Nicollette Sheridan, Heather Locklear, and Brooke Shields.

SCOTT BAIO



OWEN WILSON

Owen is known for his relationships with singer Sheryl Crow and actress Kate Hudson. But the funny Romeo has also gone out with Demi Moore, Gina Gershon, and Rachel McAdams. And, since a rekindled romance with Hudson fizzled out, we’ll keep our eyes on Owen to see who he falls for next.

OWEN WILSON



LANCE ARMSTRONG

Even though Lance has only been divorced since 2003 and spent two years with his almost-second wife, Sheryl Crow, he’s managed to squeeze in flings with Sandra Bullock, Tory Burch, Ashley Olsen, and Kate Hudson. Crow and Hudson? He and Wilson seem to have a few things in common.

LANCE ARMSTRONG



DAVID SPADE

The most unlikely of ladies' men, Spade has dated many of Hollywood’s loveliest stars, including Pamela Anderson, Lara Flynn Boyle, Julie Bowen, and Heather Locklear. When recently asked his secret, he chalked it up to being normal, consistent, and reliable. Sounds good to us.

DAVID SPADE



JOHN MAYER

Come on, girls, really? We get the falling-for-a-musician thing. Really, we do. But we only get it if you fall for a musician who’s got some talent. We do not understand why this guy's been getting so many girls…Jennifer Love Hewitt, Jessica Simpson, Kimberly Stewart, Cameron Diaz, Jennifer Aniston? Maybe they’re all pretty but tone deaf.

JOHN MAYER



CRISS ANGEL

The magic here is that any girl would fall for the over-the-top Angel, and yet he has allegedly dated Paris Hilton, Pamela Anderson, Minnie Driver, Lindsay Lohan, Cindy Margolis, Cameron Diaz, Britney Spears, and, most recently, Hef’s #1 girl, Holly Madison. Sure, some of them were reportedly business meetings, but still this mind-freak is conjuring up a lot of babes.

CRISS ANGEL



BRODY JENNER

Brody’s becoming the stud of the new millennium. The 23-year-old reality TV star and son of Olympic decathlete Bruce Jenner has been on a dating spree these last few years, hooking up with Haylie Duff, Tila Tequila, Kristin Cavallari, Paris Hilton, Nicole Richie, Lindsay Lohan, and Lauren Conrad. And even though Brody’s in development on a new reality show called Bromance, where he’ll be “dating” a bunch of guys to pick a new pal for his entourage, odds are he’ll go through many more B-list starlets and celebutantes before he settles down.

BRODY JENNER



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By Amy & Nancy Harrington, GetBack.com


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