Top 10 Celebrity Womanizers
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#10 – John Mayer
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In song, he’s a sensitive romantic with a sweet voice. In interviews, he’s an over-sharer who kisses and tells with the best of ‘em. Relationships with Jennifer Love Hewitt, Jessica Simpson, Jennifer Aniston, Taylor Swift, and Katy Perry line his résumé, so the female Hollywood elite had better watch out for this bad-boy. We guess that “your body is a wonderland” line works.
#9 – George Clooney
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Though he was married once, Clooney now represents the perennial bachelor – y’know, one of those guys who says he’ll never tie the knot again. But that doesn’t stop the ladies from fantasizing about getting this smart and suave single guy to settle down: the silver fox has played doctor with dozens of leading ladies, and always shows up to award shows with a different beauty on his arm.
#8 – John F. Kennedy
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A young and vibrant Commander-in-Chief, JFK used his good looks, charm and bags of money to land Jackie – but that didn’t stop his philandering. Acting on his father’s advice that he should “get laid as often as possible,” Kennedy allegedly bedded White House staffers, socialites, and actresses, claiming to get headaches if he went without sex for three-days-straight. How he had time left to be President, we’ll never know.
#7 – Tiger Woods
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Tiger was one of the most clean-cut, successful and high-earning athletes in the world. But that reputation unraveled quickly when scores of women admitted to “transgressions” with the famous golfer. He blamed money and fame for his easy access to beautiful ladies. Whatever the case, sexting scandals, kinky behind-the-scenes details, lost endorsements and a very public divorce ensued – all because too many women took a swing with Tiger’s wood.
#6 – Hugh Hefner
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He is the playboy: after waiting till age-22 to lose his virginity, Hef didn’t look back and started bedding anything with a bunny tail. Playboy Mansion parties of yore were legendary, and even though today his version of a business suit is a smoking jacket and silk pajamas, we’ll allow it: even into his 80s, he’s still juggling multiple Playmates at once – all of whom are decades his junior.
#5 – Jack Nicholson
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When compared to the others on this list, Jack’s exploits seem tame – we mean, he “only” claims to’ve had 2,000 partners. But his excesses when it comes to women, drugs and booze are well-documented, and Nicholson was once considered one of Hollywood’s bad boys, having broken the hearts of Anjelica Huston, Michelle Phillips and Lara Flynn Boyle, among others. Talk about an “Easy Rider…”
#4 – Gene Simmons
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Today, he’s a married father of two. But for decades, Simmons trash-talked marriage while living fulltime with Playboy Playmate Shannon Tweed. KISS’s Demon is known for his inhumanly long tongue and his reputation as a lothario, leading to claims he hooked up with over 4,600 women throughout his career. If he’s rock n’ rolling all night and partying every day, when exactly does he have time to chase tail?
#3 – Charlie Sheen
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This musta been what he meant by “winning:” Charlie ranked second on Maxim’s list of Ten Living Sex Legends. But not necessarily because of quality – here it’s the quantity that counts: about five-thousand to be exact. Sheen’s counted porn stars and famous actresses among his goddesses; but even with a “Platoon”’s-worth of beautiful women at his disposal, Sheen was still named as a client of high-profile madam Heidi Fleiss.
#2 – Warren Beatty
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He’s been married to Annette Bening since 1992, but somehow this Hollywood heartthrob still managed to sleep with over 12-thousand women – at least according to his biography. Included in the throngs are Madonna, Diane Keaton and many other big names. Folk singer Carly Simon was supposedly so bitter after her affair with him, she wrote a song – but on the plus side, Elizabeth Taylor gave his performance a 15/10.
#1 – Wilt Chamberlain
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This shy and gangly teen grew up into one of the most famous basketball players ever, becoming the only player in history to score 100-points in one game. But that’s not the only place he scored: Chamberlain was also one of the most infamous womanizers around, bedding an estimated 20-thousand ladies – but somehow avoiding diseases and illegitimate kids. We call that a slam-dunk. Do you agree with our list? Who do you think are the most notorious celebrity womanizers? For more top 10s about your favorite celebs, be sure to subscribe to WatchMojo.com.