By The Editors of GQ. As one of the most famous basketball players, and the only player to score over 100 points in one game, he reportedly had been with over 20,000 women. Terry Moore Actress | Come Back, Little Sheba . The actor is one of the shortest in Hollywood, but also one of the biggest playboys in the same time, having dated beauties like Sarah Jessica Parker, Marisa Tomei, Winona Ryder and so on. He also divorced his fourth wife, Anne of Cleves. Top 10: 21st Century Playboys Dan Bilzerian And 9 Other People You Probably Can't Stand. He also admitted to forcing a peasant girl to sleep with him and beating a prostitute when she refused him. Castro reportedly sent his guards out to the beaches of Havana to recruit beautiful women for him to sleep with. However, some of the most famous men in history were never satisfied with one woman. Or so the saying goes. Many aspiring actors will take any type of role they can get in the industry, regardless of what they are asked to do, including being naked on camera. Casanova Admitted To Raping And Abusing Women, Henry VIII Famously Decapitated His Wives. The supermodel of course. This next list is the perfect example of such individuals who were willing to do it all for fame and well, money of course. The new face of Batman has had quite a past when it comes to his dating history that includes strippers, gambling and a string of hot exes. He finally set his sights on gorgeous Latina beauty Eva Mendes who is only 6 years his senior and they now share a child. Weigh in on the sleaziest playboys in history. She is an actress, known for Playboy: Playmate Profile Video Collection Featuring Miss November 1998, 1995, 1992, 1989 (1998) and Howard Stern (1994). Stars like Jennifer Lopez, Kim Kardashian, and Nicki Minaj know how to sizzle in front of the camera — but it's all about what they have behind! R35, you are correct! 10 – Louis XIV de Bourbon . 3 on their 100 Sexiest Stars of the Twentieth Century list. The ultimate news source for music, celebrity, entertainment, movies, and current events on the web. Like art imitating life he developed a real life relationship with his on-screen love Rachel McAdams but his soulful eyes and smooth lines weren’t enough. They have to travel for work, they endure long hours on set every day and the constant gaze of the paparazzi can keep anyone on their toes. These 25 Photos Of South Florida In The 1970s Will Make You Smile. Louis XIV de Bourbon – Hyacinthe Rigaud [Public domain], via Wikimedia Commons. Some more infamously-nasty than others, it's amazing how successful trashy, moral-free women can be in America. Raquel Welch was among the most iconic sex symbols of the 60s and 70s, which put her on the top of some pretty sexy lists: According to Wikipedia "Welch was chosen by Empire Magazine as one of the 100 Sexiest Stars in Film History. A wise hussy once said “well-behaved women seldom make history” which is true in our hypersexualized culture where scandalous behavior is awarded. 15 Shawn Kemp. Henry VIII executed two of his wives. Even several popes have bragged about their illicit encounters. He was recently married to Miranda Kerr but ended the marriage after only three years. Relationships are hard work and we can only imagine having to try navigating one around the paparazzi and better yet maintain it. Unsurprisingly, many of the biggest playboys in history are also some of the most infamous figures. Check it out…. Top 10 Hollywood Playboy Playmates of All Time | Sexiest Playboy Nude Actress & Models ... often attempt to emulate the best looking women on the list as they are considered to be the great beauties of history. Guess it doesn't hurt being named Sexiest Man Alive by People magazine. The idea of hitting it big in Hollywood has always been a powerful draw, and young innocents from all over America and the world flocked to … The most notorious and prolific womanizer in sports history has to be Wilt Chamberlain. I bring Flay-vuh to being the biggest, cuntiest bitch in Hollywood History. His sixth and final wife, Katherine Parr, outlived Henry. Related to. A fresh take on sports: the biggest news and most entertaining lists. And by that we mean a scholarly examination of them, of course. For now... More often than not John Mayer has been referred to as the “quintessential douchebag” in Hollywood but the singer has no problem feeding the press with ammunition with his recent dating shenanigans. A Lothario came to be known as a ladies' man, a kind of Don Juan who will use his mi The 20 Biggest Age Difference Couples In Hollywood. Photos. So far the crooner has dated a string of Hollywood hotties including Jennifer Aniston, Taylor Swift, Minka Kelly, Vanessa Carlton, Jennifer Love Hewitt, Jessica Simpson, Taylor Swift and most recently Katy Perry. Sara Jean Underwood was last year’s Playmate of the Year and is soon to star in Spike’s new digital series “Ask a Playmate.” The petite 24-year-old with a 32B bust was born and raised in Oregon and has the distinction of being both a Playboy Playmate and being all natural…a rare and impressive feat. Bottoms up! When Fidel Castro wasn't palling around with Che Guevara, he was scouring the beaches of Havana for his next “meal.” Pablo Picasso drove two of his lovers to end their own lives. 16 of 59. Here are the ten greatest bussits, floozies and scuzzbuckets ever. While many fans focus on the scantily clad women of pro-wrestling (with a group of them gracing Playboy covers of the past), it’s time to run down the list of the hottest playboys in wrestling history. Behind every great man, there’s a great woman. He famously made the leap from Jennifer Lopez to Jennifer Garner but alas their marriage is now ending in divorce. It's no secret that when it comes to dating, Bradley Cooper is never lacking female attention. Hope Dworaczyk Smith is an American Playboy model, TV host and reality television personality. Who knew he knew how to wine and dine the ladies? But don’t let that fool you. After leaving the seminary, Casanova devoted himself to seducing women. Orlando’s been linked to the likes of Kate Bosworth, Nina Dobrev and Selena Gomez. By James Tennent. From Lord Byron to Hugh Hefner, these lotharios were not the greatest male lovers in history - they were historical womanizers who are only now being exposed for their exploits. From famous off screen love to sneaky celebrity hook ups to quickie marriages, we reveal some of the biggest moments in celebrity dating history and discover which Hollywood males have scooped the bes. Giacomo Casanova nearly became a priest before he was expelled for sleeping with another student. He may be an American actor, singer, producer and television personality but Wilmer will always be best known for his role as Fez in the sitcom That '70s Show and for the ridiculously hot list of exes he has managed to leave behind. A Hollywood Player may not always have a distinct taste, personality or even a particular type of women unless it comes to Leo Di Caprio when the order of the day is A-List actresses and hot supermodels. He also most likely spread gonorrhea and syphilis to his many partners. Making it in Hollywood is no easy feat. 11 Hollywood Stars Who Stripped Down for Playboy, From Kim Basinger to Lindsay Lohan (Photos) Kim Basinger, Jenny McCarthy and Sharon Stone are just a … Share Tweet Flip. 2. Henry VIII executed two of his wives. We reveal the Top 10 male celebs in Hollywood with the best dating track record from Leo DicCaprio to George Clooney, Bradley Cooper and more. It's pop culture on steroids. December 9, 2014 . The Hollywood actor has come a long way since his days on The Lord of the Rings and Pirates of the Caribbean. From Victoria's Secret Angels to A-list actresses, Leo has dated the likes of Bar Refaeli, Blake Lively, Gisele Bundchen, Kelly Rohrbach and even Rihanna. The King of France and Navarre ascended to the throne at the age of four and reigned 72 years, longer than any other European king in history. From famous off screen love to sneaky celebrity hook ups to quickie marriages, we reveal some of the biggest moments in celebrity dating history and discover which Hollywood males have scooped the best dating track records. Because he can, making him one of Hollywood’s biggest playboys to date. Ray J. He’s come a long way since he was Brandy’s little brother. Vote up the “charismatic” and “charming” historical figures who were, in fact, cheap manipulators obsessed with sexual conquest. Her older brother has been her biggest influence in life, teaching her snowboarding and soccer at a young age, sports she continues to enjoy to this day. Warren Beatty. Playboy model Jenna Bentley has upset her army of fans by announcing she might get a breast reduction. In the 1970s, the Environmental Protection Agency sent photographers all over the country as part of the DOCUMERICA project. 11 Hollywood Stars Who Stripped Down for Playboy, From Kim Basinger to Lindsay Lohan (Photos) Kim Basinger, Jenny McCarthy and Sharon Stone are just a … The 50 Most Unforgettable Breasts in Movie History. 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