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Hollywood’s Biggest Playboys

28 Aug

by Rodimus Dunn


George Clooney- This consummate lady’s man divorced in 1993 and stated he’d never get married again.  So far he’s been a man of his word, and has been linked to such beauties as Kelly Preston, Renee Zellweger, Lisa Snowden, Sara Larson, and Elisabetta Canalis.


Charlie Sheen- The man with Adonis DNA has been “winning” with different beauties since the 90s.  In addition to his throng of adult film actresses, Sheen has Kelly Preston, Donna Peele, Denise Richards, and Brooke Mueller as former bedroom buddies.


Adam Levine- Maroon 5’s lead man has had no problems getting quality women.  He’s allegedly been close with Kirsten Dunst, Paris Hilton, Jessica Simpson, Jessica Biel, and currently Russian model Anne Vyalitsyna.


He traded Baywatch models for baby carriages and strollers

Scott Baio- He’s famous for his roles in “Happy Days” and “Charles in Charge,” but he should be famous for the list of women in his black book.  Chaci’s former dates include Brooke Shields, Pamela Anderson, Heather Locklear, Denise Richards, Nicollette Sheridan, Erika Eleniak, and Nicole Eggert.  He messed all of this up when he married in 2007 and soon started a family.


Exclusive beach … check; Norwegian model … check; grabbing the derriere … checkmate

Josh Hartnett- PETA’s 2003 winner of sexiest vegetarian alive doesn’t have the sheer quantity of famous trysts as some of the other playboys, but the quality of these women is quite high.  Hartnett has been romantically linked to Scarlett Johansson, Gisele Bundchen, Rihanna, and Kirsten Dunst.


Justin Timberlake- He’s not the classic playboy as he’s gotten dumped a few times and dates his women for a rather long time, but JT has made the Hollywood rounds.  He’s famously dated Brittney Spears, Fergie, Jenna Dewan, Cameron Diaz, Alyssa Milano, and Jessica Biel.


First you take grandma out to lunch, then…


you take a supermodel to a Lakers game.  A day in the life of Leo

Leonardo DiCaprio- All Leo does is date supermodels … what a horrible life.  His list includes Kristen Zang, Emma Miller, Gisele Bundchen, and Bar Refaeli.



Are all of their bodies wonderlands?

John Mayer- Everyone knows all about this singer’s vast conquests because he just loves to kiss and tell.  His very impressive list of alleged conquests includes Jennifer Aniston, Jessica Simpson, Taylor Swift, Jennifer Love Hewitt, Cameron Diaz, and Minka Kelly.




Colin Farrell- The luck of the Irish is apparently very powerful.  Farrell’s large list of hotties in his rolodex has such names as Angelina Jolie, Lindsay Lohan, Brittney Spears, Paris Hilton, Rosario Dawson, Nicole Narain, Michelle Rodriguez, Denise Richards, and Rihanna.


Lifetime Achievement Award


Jack Nicholson- He is the epitome of playboy.  Jack has been linked to several models and actresses over the years including Michelle Phillips, Bebe Buell, Anjelica Huston, Rebecca Broussard, and Lara Flynn Boyle.  Even though he’s now 74, it’s rare to see this icon not flanked by a gorgeous lady, or two, 50 years his junior.


One Response to “Hollywood’s Biggest Playboys”

  1. Anonymous November 5, 2012 at 10:54 PM #

    Wow. Your site is off the chain!

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