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Our list of Hollywood's most famous male serial daters.
By Jenna Birch — Written on Nov 13, 2020
Hollywood is practically known for the dating and mating habits of its stars. The celebrity hook-ups and shake-ups happen on a pretty regular basis, making headlines across the country for their many flings.
Many men, once they reach celebrity status, get swept away by the waves of women thrown at them. They can't seem to resist, especially these boys.
Of course, there are a handful of men who've been linked to crazy numbers of ladies.
Top 10 Most Notorious Celebrity Womanizers
These select few have risen above the rest to take a spot on our list of the most notorious celebrity womanizers. Pretty big honor, right? Let's count them down.
1. Wilt Chamberlain
Chamberlain has had his own fair share of women. 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.
2. Warren Beatty
Before he put a ring on Annette Bening, the acting legend bedded a jaw-dropping 12,775 women, according to his biography. We have one word to describe our response: Insanity!
3. Charlie Sheen
We don't know if Charlie Sheen's exactly "winning" anymore since CBS terminated his role on Two and a Half Men, but he's always seemed to score with the ladies. He notched a place on Maxim's list of "10 Living Sex Legends," and his tally of women is reportedly well over 5,000.
At the ripe old age of 55, he could still have years of womanizing ahead of him, despite the rape accusations against him. Unless he settles down with a goddess for good, that is.
4. Gene Simmons
Simmons lived with Shannon Tweed, a Playboy Playmate, for decades, and married in 2011. He allegedly fell in love with Tweed while dating Cher, and reportedly slep with over 4,800 women during his nights of rock n'rolling and partying.
5. Jack Nicholson
This silver-screen icon has six children with five different women, and his number is somewhere around 2,000. But as he's gotten older and wiser, it turns out The Jack is a secret softie looking for some real lovin'. He recently revealed he would be up for one last great romance.
6. Hugh Hefner
Hefner was the brains behind Playboy. He's famous for his Playboy Mansion and the parties he threw there, as well as the thousands of women who passed in and out of his home. There was a reality show that followed his life with three live-in girlfriends, and he claims to have slept with 1,000 women.
7. Tiger Woods
Well, 2010 was the Year of the Tiger — quite literally. In late 2009, 13 women came forward claiming they'd had extramarital affairs with professional golf's golden boy.
He spent the next year dealing with the overwhelming fallout of his mistakes and finalizing that very-public divorce from his wife, Elin. Tiger's womanizing was probably the most shocking to date.
8. John F. Kennedy
Even though he was married, that didn't stop JFK from being a womanizer. His father told him that he should "get laid as often as possible."
Kennedy allegedly slept with many people on the White House staff, actresses, and socialites. If he didn't have sex for three days straight, he would claim that he would have headaches.
9. George Clooney
After his three-year marriage to Talia Balsam ended, Clooney said he would never tie the knot again — and the man kept his word... until he married Amal Alamuddin in 2014. Before settling down, he had numerous girlfriends including Kelly Preston, Teri Hatcher, Krista Allen, Lucy Liu, and Elisabetta Canalis.
10. John Mayer
If you're a talented and successful Hollywood beauty, you should probably watch out. Mayer is no doubt about to charm you... unless he already has.
The soulful singer managed to hook up with a good portion of the entertainment elite. Jennifer Aniston, Jessica Simpson, Jennifer Love Hewitt, Mandy Moore, Minka Kelly, and Taylor Swift are among his conquests, and we don't exactly hear any of those gals singing his praises.
In fact, it's the opposite. Swift told us all we needed to know about Mayer's ways on her track, "Dear John": "All the girls that you've run dry have tired, lifeless eyes 'cause you've burnt them out." Ouch. And Jessica Simpson opened up about their relationship in her memoir.
Jenna Birch is a freelance journalist for women’s magazines and national websites, strategist, and author of 'The Love Gap: A Radical Plan to Win in Life and Love'. Visit her website for more of her work.