10 Greatest Womanizers in History

By Richard on December 14, 2020 Comments: 30

While some men are happy to find ‘the one’ and settle down with a life of monogamy
stretching out before them, others remain resolute bachelors and delight in the thrill of
the chase. Some men take playing the field to a whole new level. The confidence and
magnetism of the men in this list has helped them seduce thousands of women into sharing
their bed. Of course, fame, power and riches can help things along quite a bit, too.

The following list is comprised of men who, if they kept track of their nocturnal conquests
with the traditional notches carved into their bed posts, would soon be sleeping amongst
matchwood.

Every fisherman exaggerates his catch, but even if these gents were dividing their tally by
five their scores would still be enviably substantial. They must be drinking a hell of a lot of
energy drinks.

10. Jack Nicholson

Sexploits: 2,000 easy rides

Kim Basinger said of Nicholson: “He is crazy! I haven`t met anyone so obsessed with sex like
him!” The veteran actor would agree that that’s a fair summing up of his sexual proficiency.
When asked how many children he has fathered, he responded to the interviewer: “There
could be 9,000 for all I know – I used to live so freely. Women are never enough for me.
There were days when I used to go to bed with four or more. But none of them can take
away my freedom. Until the end of my days I’ll remain a bachelor!”

Nicholson’s youthful excesses are well documented. “I’ve slept with all women, I’ve tried
every single drug and all kinds of liquor!” he has said. The womanizing never got in the way
of his stellar Hollywood career, though, as he’s won 3 Oscars and been nominated 12 times.

The 73 year-old has admitted that he is starting to wind down now and feels a little
conspicuous hitting on young women. He also apparently only uses Viagra when he’s
with more than one lucky lady. And there are still quite a number of women queuing
up for Nicholson’s attentions: “Happily, when it comes to girls hitting on me, I’m not
undernourished.”

9. Hugh Hefner

Sexploits: 2,000–5,000 bunnies bedded

Surely the most famous of today’s lady-killers, Playboy entrepreneur Hugh Hefner is
probably the most unsurprising entry in this list. An accurate figure for the number of his
sexual conquests is difficult to nail down, but estimates range from 2,000 to as much as
5,000, and not just women either – Hefner freely admits to having bisexual liaisons.

Hugh Hefner opened his account at an unexpectedly late age of 22, but since he launched
the first issue of Playboy in 1953, with Marilyn Monroe’s image gracing the front cover, he
hasn’t looked back.

Even today and well into his 80s, he is rumored to keep a bowl of Viagra next to his (well-
used) bed and even provide them for his guests. He still has orgies twice a week with various
playmates, too: “I have slept with thousands of women, and they all still like me.”

8. Julio Iglesias

Sexploits: 3,000 señoritas serenaded and then some

Spanish crooner Julio Iglesias is known for his love of the ladies almost as much as his
romantic music. It is oft-reported that Iglesias has made sweet, sweet love to more than
3,000 swooning women, a figure that the singer himself doesn’t contradict: “That probably
was until 1976,” he said, “so they didn’t count the other women.”

The Iberian Romeo started early, too: “I love the girls like crazy, really, like crazy, since I was
4 years old.” Well, his dad was a gynecologist so it must run in family.

For Iglesias, sex is just as natural and commonplace as the red wine he loves: “I am intensely erotic.

For me, sex is as vital as sleep. I do it through desire, through necessity, but always
with joy. I am a lover for sure. I love to be loved.”

7. Ron Jeremy

Sexploits: 4,000-5,000 porn partners poked

Over an amazingly successful career that has spanned decades, porn star Ron Jeremy has
sexed his way through thousands upon thousands of partners. The ‘hedgehog’ has starred
in more than 2,000 skin flicks and is quite possibly the most famous male porn star ever
to have thrust himself into the limelight. If there was ever to be a king of porn it would be
Jeremy, and if accounts of encounters with him are to be believed, he’s a rather nice fellow
to boot.

He makes up for his short stature, chubby physique and hirsute frame with a penis that
measures almost 10 inches long and a legendary sexual stamina (he once had sex with
fourteen different women in four hours). When asked about his and Gene Simmons’ (entry
number 6) conquests he said:

“We both say between four and five thousand, which is true. But he’s a rock star – they’re
doing him because they like him. They’re doing me because it’s a paycheck. Or, the other
line is, he gets girls that look like his Playboy playmate wife, and when I’m not making
movies, I get girls that look like Gene Simmons.”

6. Gene Simmons

Sexploits: 4,600 crazy, crazy nights

He’s sold over 100 million records, never been married, and counts Cher and Diana Ross
among his tally. He claims that none of his partners have ever complained, even when he
tells them he wants to bed their friends or relatives.

“I have not heard a complaint. That’s because I am straight with them. I don’t lie, like most
men do. I will tell a girl I want her and desire her, but I’ll tell her straight, ‘I want your sister
and your mommy as well’.”

It must be his famously prehensile tongue: “It’s ironic that I’m mostly known for my tongue
which is a hideous thing. But it’s every girl’s best friend – no batteries required.”

Rivaling Ron Jeremy, the KISS frontman alleges to have had fornicated with an estimated
4,600 women (many of those while he was with girlfriend Shannon Tweed, who doesn’t
seem to mind). Apart from an insatiable sexual appetite, Simmons has some home-grown
philosophy behind his enthusiasm for the ladies:

“The male species manufactures billions of sperm – it’s our duty to do what the Old
Testament says, which is ‘Spread Thy Seed’.

“The only problem with women is that they think all those sperm we make is just for them.
But the honest truth is it’s not. I would urge all guys to stop lying to women.”

5. Charlie Sheen

Sexploits: 5,000 hot shots

You’d have thought that being an attractive Hollywood movie star with a famous family,
huge properties and a substantial bank balance would be sufficient to bring enough women
to any man’s door to satisfy his loins. But not Charlie Sheen. Sheen was famously named
in the Heidi Fleiss Hollywood prostitution scandal as one of her most regular clients. He
certainly has a soft-spot for the ladies – in fact it seems like he cannot get enough of them,
and his reputation as a serial philanderer seems well deserved. Aside from frequenting
ladies of the night, it is alleged that he heavily indulges in internet porn (according to ex-
wife Denise Richards – they split after he allegedly told her she was among the hottest 1,000
women he had slept with) and still manages to make headlines with his raucous hotel-based
antics.

4. Umberto Billo

Sexploits: 8,000 guests checked out (and more)

“Who is this Umberto Billo?” I hear you cry. Well, he is an Italian so mysterious it’s hard to
even track down a photograph of this elusive Casanova. Uniquely for this list he isn’t rich
or famous but simply a hotel porter at the Venetian Hotel in Las Vegas. Here’s what men’s
magazine Maxim had to say about him: “Despite lacking fame, wealth, and U.S. citizenship,
this Italian hotel porter insists he’s made around 8,000 women happy sometimes
entertaining four tourists a night. Umberto, whose talents came to worldwide attention
when he appeared on the British TV show Eurotrash, claims he inspired tremendous ‘brand
loyalty.’ An American businesswoman commented: “I must have spent thousands in the
hotel because of him!”

The man himself added, “They crossed oceans to see me.” But not everything was rosy
for the permanently-tired porter as he was sacked for being too tired to carry the guests’
luggage. He claimed that he also had ‘an insatiable wife.’ No wonder he was tired!

3. Warren Beatty

Sexploits: 12,000 bonnies banged

He’s bedded some of the most desirable women in Hollywood: Natalie Wood, Brigitte
Bardot, Jane Fonda, Joan Collins, Carly Simon (Beatty is alleged to partly be the subject of
Simon’s song You’re so Vain), Faye Dunaway, Leslie Caron, Candace Bergan, Isabelle Adjani,
Julie Christie and Madonna to name a handful. But that list is, ladies and gentlemen, merely
the tip of the iceberg.

In Peter Biskind’s biography of actor Warren Beatty, the acclaimed Hollywood writer
estimates that the famous lothario has achieved a jaw-dropping 12,775 sexual
conquests: “Using simple arithmetic… 12,775 women, give or take, a figure that does not
include daytime quickies, drive-bys, casual gropings, stolen kisses and so on.”

Elizabeth Taylor commented of Beatty’s performance between the sheets: “Out of 10, I’d
give him 15.” Joan Collins allegedly “stumbled exhausted out of bed after a steamy session
with Beatty exclaiming: “I don’t think I can last much longer. He never stops – it must be all
those vitamins he takes.”

2. Wilt Chamberlain

Sexploits: 20,000 slam dunks

Wilt Chamberlain’s 1991 autobiography, A View from Above, goes some way to revealing
the extent of the basketball star’s sex drive. A cool 20,000 women shared Chamberlain’s
(extra long) bed at one time or another. As Seymour Goldberg puts it: “Some people collect
stamps; Wilt collected women.”

If Chamberlain did indeed bed that many lucky ladies, he certainly had the tool for the job.
Friends of the man asserted that he possessed an 11 inch member that would sometimes
pop out of his shorts during games.

Acknowledged as one of the greatest players in the history of the sport (he once scored 100
points in a single game), Chamberlain defended his astounding sexual statistics, saying that
he never bedded a married woman, and added: “I was just doing what was natural—chasing
good-looking ladies, whoever they were and wherever they were available”

Chamberlain died of congestive heart failure on October 12, 1999 in California.

1. Fidel Castro

Sexploits: 35,000 hot latinas

The ex-Cuban leader’s bedroom habits came to light in a 2008 documentary by Ian
Halperin. In it, a former official close to the Marxist politician claims that he has slept with
a staggering 35,000 women. Apparently, a ‘special security team’ would be assigned to
Havana’s beaches each day to ‘recruit’ the most attractive women.

“He slept with at least two women a day for more than four decades – one for lunch and
one for supper. Sometimes he even ordered one for breakfast.”

Castro had been in power since the 1959 overthrow of dictator Fulgencio Batista’s
government, only retiring in 2010 due to ill-health. Halperin’s source – a man named Ramon
– gives the reason for his longevity: “I don’t think he would have stayed on as long as he
did if not for all the incredible women he had access to as president.” Bedding incredible
women is certainly one of the better job bonuses.

Famously, the US has tried hard to get rid of him, but Castro has outlasted every president
that had him in their sights.

The bottom line is this, fame and fortune is unsurprisingly what a woman looks for in a man.

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