10 – Louis XIV de Bourbon . Alas, the actor and singer is now happily married to fellow actress Jessica Biel and they share a wonderful son together. Shares. Because he can, making him one of Hollywood’s biggest playboys to date. 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. The Cuban dictator Fidel Castro supposedly slept with 35,000 women in his lifetime. Self | Playboy: Playmate Profile Video Collection Featuring Miss November 1998, 1995, 1992, 1989 Tiffany Taylor was born on July 17, 1977 in Leesburg, Virginia, USA as Summer Hanson. Does he even have a dating type? Who knew he knew how to wine and dine the ladies? The 20 Biggest Age Difference Couples In Hollywood. Hope Dworaczyk Smith is an American Playboy model, TV host and reality television personality. August 27, 2012. carnal-knowledge.jpeg. Henry VIII executed two of his wives. Louis XIV de Bourbon – Hyacinthe Rigaud [Public domain], via Wikimedia Commons. George Clooney’s dating type seems to be beautiful brunettes but then again blondes aren’t out of the question… His list of girlfriends over the years include Kelly Preston before she became Mrs. John Travolta of course, British model Lisa Snowdon, Parisian waitress Celine Balitran, Las Vegas cocktail waitress Sarah Larson, Michelle Pfeiffer's sister Dedee Pfeiffer, Italian beauty and TV personality Elisabetta Canalis and most recently former WWE Diva Stacy Keibler. Playboy: 10 biggest moments in the magazine's history Following Hugh Hefner's death, we count down the most shocking covers in his iconic magazine's history. Photos. Castro reportedly sent his guards out to the beaches of Havana to recruit beautiful women for him to sleep with. Or even two, or three or four. Check it out…. 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. This next list is the perfect example of such individuals who were willing to do it all for fame and well, money of course. In some circles, sleeping with thousands of women is ostensibly a badge of accomplishment. Even several popes have bragged about their illicit encounters. Weigh in on the sleaziest playboys in history. Let’s face it: Ryan Gosling was always one of the most sought after men on the planet and after The Notebook aired it was just game over. Making it in Hollywood is no easy feat. Playing Tony Stark in Iron Man has sure helped Downey look like someone taller. 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. He famously made the leap from Jennifer Lopez to Jennifer Garner but alas their marriage is now ending in divorce. Despite being more elf than actor he still managed to accrue a hot list of exes ranging from Victoria's Secret models to Oscar winning actresses. In the 1970s, the Environmental Protection Agency sent photographers all over the country as part of the DOCUMERICA project. 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. Sharon Stone will do down in history as one of the biggest sex symbols in Hollywood history. Soon that fizzled but not before Ryan became an internet meme and viral sensation. 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. But at least one of the men repented shortly before his passing, warning others not to idolize his freewheeling lifestyle. 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. 7 Reasons why Batman is the BEST! Playboy model Jenna Bentley has upset her army of fans by announcing she might get a breast reduction. 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. Here are the ten greatest bussits, floozies and scuzzbuckets ever. 10 Great Womanizers Throughout History. She told my mother that women in the Hollywood crowd wanted to have sex with John because of his size.John Ireland was a major womanizer for this reason. Just like the characters he plays, Clooney is as suave as they come. Well apparently not as he has dated everyone from Oscar nominated actresses to Grammy award winning singers and models. According to Scotty, Tony was incredibly taken by porn star Linda Lovelace after her first and most iconic film, Deep Throat, was released.So taken, in fact, that he wanted Bowers to arrange a … Novarro was Mexican and Valentino was Italian, which quickly led tabloids to … Despite being more elf than actor he still managed to accrue a hot list of exes ranging from Victoria's Secret models to Oscar winning actresses. By GQ Staff 7 February 2017. 8 stars known in the Hollywood realm for their playboy rep. George Clooney. 0. 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. Itimes Updated on May 09, 2016, 11:03 IST The world has seen some of the most arrogant and egoistical playboys, who would do anything to make themselves feel like total studs. : https://goo.gl/I2VCGb For more such COOL stuff, SUBSCRIBE! In Don Quixote, the famous adventure story, the name Lothario came to signify the “unscrupulous seducer of women”. 13 Suave Playboys Throughout History Who Are Actually Total ... Top 10 womanizers | Kansas jayhawks basketball, Basketball ... 10 Most Famous Womanizers in History. Rush, the Hollywood depiction of the 1976 title battle between James Hunt, a man who barely followed his own rules, and Niki Lauda, then a two … A bevy of women plus two seasons of ‘For The Love Of Ray J’ a super famous relationship with Kim Kardashian and now another show on VH1 where yet more women are fighting for his affection. Best Celebrity Butts of All Time. For centuries, society has cheered on men who rack up the greatest number of “conquests” - conquests of women, that is. His sixth and final wife, Katherine Parr, outlived Henry. 8. News on all your favorite celebs, reality TV, and movies. Some more infamously-nasty than others, it's amazing how successful trashy, moral-free women can be in America. Her 1990 Playboy cover illustrates why. Women want to date him and men want to be him. In 1943, at age 61, Picasso reportedly told his 21-year-old mistress that “women are machines for suffering.” He added, “for me there are only two kinds of women, goddesses and doormats.”. But don’t let that fool you. A wise hussy once said “well-behaved women seldom make history” which is true in our hypersexualized culture where scandalous behavior is awarded. 2. via slamonline.com. He also admitted to forcing a peasant girl to sleep with him and beating a prostitute when she refused him. It was an interesting week for playboys … The 20 Biggest Playboys in Sports History. Gosling went on to dabble in Cougarville with Sandra Bullock when he was just 21 and she 37 and then again with Famke Janssen enjoying a 16 year age gap. 16 of 59. It looks like the list of celebrity sex tapes is Affleck free. These 25 Photos Of South Florida In The 1970s Will Make You Smile. 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 … Take a look. Just like the characters he plays, Clooney is as suave as they come. People young and old swoon over him. Is it so wrong to want to live in a world where Justin Timberlake and Britney Spears made it? The rock ‘n’ roll icon of the 1960s group Gary Lewis and the Playboys blames his father is in part responsible for the death of his younger brother. December 9, 2014 . Unsurprisingly, many of the biggest playboys in history are also some of the most infamous figures. 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. Orlando’s been linked to the likes of Kate Bosworth, Nina Dobrev and Selena Gomez. He told the Globe, “Joe had problems his entire life and I blame our father. by Anonymous: reply 65: 02/10/2014: "Cultivating whatever gave pleasure to my senses was always the chief business of my life," Casanova wrote in his autobiography. To woo his second wife, Anne Boleyn, Henry VIII sent her a deer he had killed himself and a note that read, “Hoping that when you eat of it you may think of the hunter.” His tune changed, however, when she failed to bear him any male heirs after they were married. The supermodel of course. My mother used to have a friend who was a costume designer in Hollywood. See why it comes as no surprise that John Mayer has made the cut now? Without further ado, here are the top 15 playboys … He has dated everyone from Disney stars to co-stars to Oscar winner actresses to pop divas. 15 Shawn Kemp. Vote up the “charismatic” and “charming” historical figures who were, in fact, cheap manipulators obsessed with sexual conquest. 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. Keep up to date with Chia on Twitter & Instagram @thesocialitesa and visit her website at www.thesocialite.co.za. Casanova Admitted To Raping And Abusing Women, Henry VIII Famously Decapitated His Wives. She first gained fame as Playboy magazine's Playmate of the Month for April 2009 after testing for the 55th Anniversary Playmate search, and later became the 2010 Playmate of the Year. So far Wilmer has been linked to Lindsay Lohan, Jennifer Love Hewitt, Mandy Moore, Minka Kelly, Ashlee Simpson, Rihanna, Avril Lavigne and his on again off again love Demi Lovato. After the boy band era and bad hair days, Justin moved on to become much cooler than he should have. Biggest Male and Female Whores in Hollywood By Terry Shropshire | November 3, 2012 | 8 Some people will do anything to become famous, maintain fame or rise up in the hallowed Hollywood … Bottoms up! 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. Our dear Mr. Cooper has been romantically linked to the likes of Zoe Saldana, Jennifer Lopez, Cameron Diaz, Jennifer Aniston, Renee Zellweger, and even Jennifer Esposito. Then again he would never limit his dating pool to just supermodels as he’s also been known to having dated Erin Heatherton, Amber Valletta, Helena Christensen and even Bridget Hall. 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 … You would think Hollywood is such a big place but alas, it seems like everybody is dating everybody and some dates are placed on repeat. In the 1930s, Picasso left his first wife, Olga, for his pregnant mistress, but he refused to divorce Olga, preventing her from inheriting any of his wealth. After leaving the seminary, Casanova devoted himself to seducing women. Next on the ranking is Orlando Bloom. It's no secret that when it comes to dating, Bradley Cooper is never lacking female attention. Behind every great man, there’s a great woman. He even paired partners with his meals, aiming for a different “lunch” and “dinner” partner every day. He was recently married to Miranda Kerr but ended the marriage after only three years. And by that we mean a scholarly examination of them, of course. It's safe to say no one will ever have to describe any of Orlando's ex-girlfriends with an awkward pause followed by a "but she has a great personality." Giacomo Casanova nearly became a priest before he was expelled for sleeping with another student. The most notorious and prolific womanizer in sports history has to be Wilt Chamberlain. His guitar skills and smooth voice just fuel his fire as he leaves a string of broken hearts across the Hollywood boulevard. Top 10: 21st Century Playboys Dan Bilzerian And 9 Other People You Probably Can't Stand. 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. He also divorced his fourth wife, Anne of Cleves. First to make it onto the Top 10 list is none other than A list celebrity actor Ben Affleck. Stars from Cameron Diaz to Matt LeBlanc got their start by showing a lot of skin — click through to see which celebs kicked off their careers in porn By Elias Ahmed. Then again in Hollywood standards, 10 years of wedded bliss with three kids isn’t too bad going. Hollywood has always been a highly sexed town full of attractive young people with plenty of money or needing plenty of money. The 50 Most Unforgettable Breasts in Movie History. Some had insatiable appetites, using their fame, wealth, power or even their natural charms to … The 28-year-old is known in part for her large 36E breasts, which are natural — … Both Ramon Novarro and Rudolph Valentino were well-known leading men of the 1920s, famous for their roles as dashing young romantics in films like Mata Hari and The Son of the Sheikh. A fresh take on sports: the biggest news and most entertaining lists. His preferred dating type you ask? Guess it doesn't hurt being named Sexiest Man Alive by People magazine. The ultimate news source for music, celebrity, entertainment, movies, and current events on the web. The biggest womanizers in history. We took a peek through Justin's ex files to see the succession of broken hearts he's left behind and they include the likes of Ashley Olsen, Olivia Wilde, Alyssa Milano, Scarlett Johansson and even Cameron Diaz. Then again, celebs do have access to a great choice in excuses when it comes to breaking up. Number one on the list has to be without a doubt Oscar winner Leo DiCaprio. 10 – Louis XIV de Bourbon . Henry VIII executed two of his wives. The Hollywood actor has come a long way since his days on The Lord of the Rings and Pirates of the Caribbean. One this is for sure, all of these women are stunning but only one of them can be the prettiest woman of all time. 3 Orlando Bloom. Sources: www.radaronline.com, www.celebuzz.com, Chia Kougianos is a TV Presenter as well as the Editor for TheSocialite.co.za You can also catch her on the Trace Sports channel where she guest presents the Top 20 shows. Related to. His third wife and the only one to produce a surviving male heir, Jane Seymour, died of blood poisoning. 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. 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