50 Greatest Modern Day Playboys and Past Casanovas

There’s a certain type of man that doesn’t seek relationships, his quest is sexual in nature, and his interests lie in sexual domination (sexual addiction). Some call him a Casanova, playboy, womanizer, or even a lady-killer. Either way, he represents a select group of men who are (perhaps) unable to be fulfilled through a meaningful relationship, and so he is driven by his conquests.

“There is a range of factors that drive men (and women) to sleep with multiple partners,” explains Jessica O’Reilly Ph.D., host of the Mind-Blowing Oral: Clitoris Edition video course. “Evolutionists would suggest that men have an innate desire to ‘spread their seed’ and ensure the prorogation of offspring—On the sociocultural side, men are socialized (and pressured) to seek out sexual encounters and in many cases, they’re rewarded for these sexual conquests.”

And the kind of reward we’re talking about is both physical and emotional. Becoming a player is an addiction, an adrenaline rush, and a tangible indicator of a man’s worth. To be known as the man who has slept with the most females is an accomplishment that many would admire.

“Men who ‘score’ with many women are held in high regard,” describes Raffi Bilek LCSW-C from the Baltimore Therapy Center. “We get little credit from our buddies for how long we’ve been in a relationship, but lots of high-fives for hooking up with an attractive woman, and the more the better.”

And so we set out to find this man – the ultimate Cassanova, but it became practically impossible to define him based on numbers alone, so we sought out the advice of the experts. According to Richard La Ruina, the founder of PUA Training and author of “The Natural”, the true masters of the pickup should include the likes of five men: Fidel Castro, Wilt Chamberlain, Warren Beatty, and Charlie Sheen.

We tried to think of just one man who embodied the charisma, charm, and success of all the above masters, and we couldn’t think of one. And so we turned to fiction. Who is perhaps one of the greatest fictional representations of the ultimate casanova? David Wygant, a celebrated dating and relationship coach believes it could be Sean Connery from the original 1960s, James Bond.

The original James bond set the standard for not only actors, but men all over the world wanted to be Bond, and women all over the world wanted to sleep with Bond.”

-David Wygant

And now, perhaps, we are finally getting somewhere. We are beginning to understand the attributes that make up a worthy adulterer. But we were curious to learn more about these masters. And so we sorted through the world’s most worthy Casanova’s touting the most impressive conquest numbers, including Hugh Hefner, Gene Simmons, and a Las Vegas hotel porter named Umberto Billo who claims he’s sampled no less than 8,000 women over his luggage-toting career.

But in the end, there were only 50 who deserved recognition. Yeah, that may sound like a lot, but we guarantee each story to be quite unique.

Leonardo Di Caprio

Leanardo DiCaprio

The typical night for Leo is rolling into 1 Oak at Rec Room in South Beach Miami with one beautiful woman (let’s say, Toni Garrn for argument) and then leaves a couple of hours later with 20 sizzling models in tow. No lines are given, or numbers exchanged… just an unspoken Hollywood attitude that seems to pull women into his grasp.

Claimed Conquests: 9,125 models, according to Jimmy Kimmel (not the best source, but we believe him)

Living as a player is the preferred lifestyle of Leo, who is now in his forties and seems to have two requirements for the women he spends his time with. One, they understand that he prefers ‘ordinary girls,’ and two, that his version of the ordinary is best described by a photoshoot for Victoria Secret, Versace, and Calvin Klein. These are the average everyday type of supermodel, including the bikini-perfect body of Bar Refaeli, Helena Christensen, Erin Heatherton, Bridget Hall, and of course, Gisele Bundchen.

George Clooney

When it comes to dating, most top rated players are lucky to have experienced one lady from Hollywood’s A-list. George Clooney has averaged somewhere around one per year since the mid-’90s. But A-listers are not really his thing. He’s been known to hook up with everything from top models to law students and waitresses. One thing we can say about George is that he likes what he likes, and that’s the only thing his lovely exes seem to have in common with each other.

George kicked off 1995 with TV host and MTV VJ, Karen Duffy. He followed her up with Paris waitress/law student, Celine Balitran, which he brought home with him to Los Angeles. The Melrose Place beauty, Brooke Langston, was next on the list, followed by Krista Allen, Lisa Snowdon, Rene Zellweger, and Teri Hatcher. Another waitress (this time the cocktail variety) would capture his attention in 2007, before sampling the likes of Elisabeth Canalis and Stacy Keibler. Amal Alamuddin may have taken him off the market since 2014, but only time will tell if he’s gone for good.

Very few men are Playboys/Casanovas or even cheaters for their entire life. Even George Clooney and Warren Beatty got married and started families. Albeit, George was 53 and Warren was 55.”

Kevin Darné, author of My Can’t Won’t Bark! (A relationship Epiphany)

Cristiano Ronaldo

Cristiano Ronaldo

Cristiano is a great player, both in soccer and picking up women. But if we had to choose between his two skills in order to celebrate his true calling in life, we’d actually be torn as to which game he was better at playing. Over the last decade, he has scored a lot of goals for Portugal and Madrid.

Claimed Conquests: He’s just getting started (we’ll give him 10 more years)

However, the ‘scores’ we remember best include his legendary hookups with Isabel Figueira, Diana Chavez, Soraia Chaves, Gemma Atkinson, Karina Bacchi, Bipasha Basu, Maria Sharapova, Nereida Gallardo, Alice Goodwin, Paris Hilton, Raffaella Fico, Imogen Thomas, Kim Kardashian, Irina Shayk, and Lucia Villalon. And we do have to apologize to quite a few lovely ladies of whom we just didn’t have enough space to mention. But believe us when we say that your sacrifices have not gone unnoticed.

The reality is that there are so many different types of great lovers — and sometimes they’re not obvious.”

April Masini

Adam Levine

adam levine

“There are two kinds of men,” Adam Levine once said. “There are men who are f—ing misogynist pigs, and then there are men who just really love women.” And while it may sometimes be difficult to decipher between the two, Adam has been known to mix some gentlemen conduct in between his player-esque antics.

Claimed Conquests: It’s not always the number – but the quality that counts.

Levine publicly apologized to all the women he’d played (wronged) before his wedding day in 2014, including apologies to Jessica Simpson, Jessica Biel, Maria Sharapova, Angela Bellotte, Arielle Vandenberg, Cameron Diaz, and many others. But can a former player ever be reformed?

Often called ‘players,’ [womanizers are] often associated with a category of mental health disorders called personality disorders. Inherent in the disorder, both emotionally and neurologically, are deficits in the brain regions responsible for attachment and bonding, and empathy and emotional intimacy. Chronic womanizers who are never reformed by ‘the love of a good woman’ are often the possessors of the disorders whose brain wiring prevents bonding and intimacy.”

Sandra L. Brown, author of ‘How to Spot a Dangerous Man Before You Get Involved’ and ‘Women Who Love Psychopaths’

Alex Rodriguez

At the age of 18, Alex Rodriguez (“A-Rod”) debuted as a major league player for the Seattle Mariners. Fourteen years later he would become the youngest player to successfully hit 500 career home runs. However, those 500 grand slams were nothing compared to the bases he was rounding with the likes of countless escorts, strippers, C-list models/actresses, B-list models/actresses, and also an impressive number of Hollywood A-listers. A few of A-Rods highlights include Cameron Diaz, Kate Hudson, and Madonna. But perhaps the most impressive thing about his list, is many of these women come right after the other, and several even overlapped.

A-Rod was connected to the fitness model Alicia Marie, while also being spotted with a collection of high-profile strippers. He was connected with Hudson while also seeing Elaine Spottswood, and could be said to have been practically dating identical twin sisters when both Cameron Diaz and Ella Magers were sharing his bed. He became the ‘other man’ with such married beauties as Jessica Sekely (married to Jose Conseco at the time) and Madonna (married to Guy Richie), and we know at least one of those hookups he was also married (briefly). In 2017, he married Jennifer Lopez but we are not about to say the rest is history.

Colin Farrel

“Love is – complicated – sex is much easier,” Colin Farrell once told the Irish Mirror. “If I could have interesting conversations after sex, I would be in heaven.” And it doesn’t get any more complicated than the many women that Colin has wooed into bed by his bad-boy image, only to cast them away afterward for being ‘too boring’ (and we might also suggest a few of them to be, ‘too crazy’).

Age has no boundaries to a man like Colin, who has dated women ranging from just barely out of the crib (Amelia Warner) to one foot in the grave (Elizabeth Taylor, who was then 79). A couple of the highlights throughout his career include Rihanna, Carmen Electra, Lindsay Lohan, Rosario Dawson, Nicole Narain (Playboy), Demi Moore, Britney Spears (he denies it, and we don’t blame him), Angelina Jolie, Ashley Scott, and Michelle Rodriguez. He’s slowed down a bit in recent years since his sons have taken the priority in his life, but he’ll be back.

Men that are womanizers are not incapable of having real relationships but rather they haven’t found the woman that challenges them enough to want to change their lifestyle – They think the game is more rewarding than the risk of emotional vulnerability.”

Chloé Miller, Relationship Expert and Founder of And, Swipe Right

John Cusack

Only one of the two things you likely think about when you hear the name, John Cusack, is likely true. He’s that sappy nerd who always gets the girl in the end, right? Yeah, he does get the girl, but he is much blunter in real life. He is rumored to have shown up at Jennifer Love Hewitt’s front door for a first date and propositioned her for sex immediately because he had an early morning the next day.

Needless to say, Miss Hewitt did not fall for John’s notion of first date etiquette. But plenty of other women have, including Minnie Driver, Neve Campbell, and Claire Forlani. These days John still brings in the hot young women, but says he is continuously disappointed when he hears the phrase, “You’re my mom’s favorite actor.”

Russell Brand

If you’ve ever doubted the power of a comic versus a rockstar, read this quote from Russell Brand: “I’d do a gig and four or five women would come back [to my room].” And according to the comic, these women were down for sharing. So Brand would always indulge in overlapping these women on top of one another into a sloppy-second goulash he has referred to as “Blissful.”

And while many of these women will remain unnamed as far as the tabloids are concerned, the ones we will remember include Kate Moss, Moss’s best friend (Sadie Frost – also the mother of Jude Law’s three kids), Imogen Thomas, Holly Madison, Courtney love, and ex-wife, Katy Perry. 

According to an interview with GQ, Brand’s six points to success include: 

  1. Be adventurous. 
  2. Know your brand. 
  3. Avoid singles bars and clubs. 
  4. Never be blunt (Cusack, are you reading this?) 
  5. Speak postmodern 
  6. Stay confident.

Wilmer Valderrama

There are certain rules that the ladies man live by beyond the obvious one, to seduce women. These include living their life and allowing the women they play to tell their story (both the good and bad). This rule has been carried out by many legends, including Frank Sinatra, Warren Beatty, and Jack Nicholson. But for Valderrama, he officially broke that rule during a session with Howard Stern by describing his sex sessions with various Hollywood stars like he was reading from a bullet-point list.

And while Valderrama will never be a legend, we can’t deny his conquests with Jennifer Love Hewitt, Mandy Moore, Ashlee Simpson, and Lindsay Lohan. We’d love to share the technique that has brought him such good fortune over the last couple of decades, but the truth is, his most effective tool is the above-average manhood he’s been rumored to be endowed with.

Stephen Dorff

A swinger occasionally has no idea he fits the definition of a pickup artist. Stephen Dorff has repeatedly denied being the kind of man who prefers to love and leave. He also denies having dated any true Hollywood hotties since he was young.

However, the numbers don’t lie. Stephen has been connected with such women as Pamela Anderson, Angelina Jolie, Alicia Silverstone, Bridget Hall, Alicia Silverstone, Rachel Stevens, Reece Witherspoon, Michael Stipe, Kayla Jones, and Dakota Johnson. And his method of seduction is rumored to be very aggressive, which fits his onscreen bad boy image.

Josh Hartnett

Josh Hartnett

When a man feels like he can do “whatever the hell he [wants],” his confidence can become an unstoppable force. In the case of Josh Hartnett, he may be confident, but his style of attracting women is a careful balance of both confidence and vulnerability. The confidence attracts women initially, and his underlined vulnerability holds their interest.

A few of the women who have been drawn to Josh’s sensitive side include Amanda Seyfried, Scarlett Johansson, Sienna Miller, Gisele Bündchen, Julia Stiles, Tamsin Egerton, Penelope Cruz, Mischa Barton, and Helena Christensen. But the Black Hawk Down also admits that attracting Hollywood’s finest can be a bit of a downer. This is because, according to Josh, they can be just as incompatible as any other woman, but your friends will not be there to console you when you complain. Sounds like the best kind of problem to have.

Jude Law

Jude Law

A true gentleman is how Jude Law sees himself. He believes in being kind and considerate to everyone, including half the world’s women – one at a time. But one man can only have so much bad (and good) luck, so let’s see if we can’t sort out where Jude’s life has gone both right and wrong.

Jude met Sadie Frost in the ’90s. She was married with a child, and just a year later she was divorced and re-married to Jude. Some years past and news spread that he had knocked up a Chicago lap dancer. Sadie went her own way, leaving Sienna Miller ripe at 22-years-old, and Jude was more than willing to do the ‘picking’. They met during the filming of Alfie, and everything looked pretty good. They had kids, which lead to a nanny, which in turn lead to Jude sleeping with the nanny, which was not good.

From here, Jude began working on his black book, which would include underwear model, Susan Hoecke, and then Kimberly Stewart (Rod Stewart’s daughter), and a New York hotty by the name of Samantha Burke, who would end up pregnant with his fifth child. Then there was Ellen Crenshaw, a wardrobe assistant, Victoria’s Secret model, Alicia Rountree, and a Playboy model by the name of Linda. He then knocked up Catherine Harding, dated a French woman named Rachel Bourlier, and settled in with a 30-year old named Phillipa Coan.

We could go on… but there really isn’t much point.

The desire to have sex with multiple partners isn’t normal and healthy. You don’t have to be monogamous to have a happy, meaningful relationship; you need to negotiate your specific arrangements and rules with your partner and be mindful and open to their shifting emotions and needs.”

Jessica O’Reilly (Sexologist PhD)

Ryan Phillippe

Ryan Phillippe

Ryan Phillippe is said to prefer his women to be independent and strong, and we’d imagine that’s because that variety tends to get dumped with much less drama. Ryan was married to Reese Witherspoon until actress Abbie Cornish caught his eye in 2006. Cornish was followed by model Alexis Knapp, actress Amanda Seyfried, singer Rihanna, and model Paulina Slagter.

There have been several notable hookups worth mentioning, including Nikki Reed, Lindsay Lohan, Ashley Greene, and countless other nameless, beautiful women leaving a nightclub wrapped around his arm. Let us know if we’ve forgotten anybody.

Kevin Connolly

Kevin Connolly

Some philanderers have superb technique, and others simply take advantage of their media status to meet women. In the case of Mr. Connolly (the character, Eric, from the successful series and film, Entourage), it is the ladder that allows him to make this list.

And while we would not consider him to be worthy as a teacher to the art, we’d accept his invitation as a wingman any day – with the likes of such women as Chloe Sevigny and Hayden Panettiere under his belt. 

Tommy Lee

Tommy Lee

As a three-time loser in the game of marriage, we suspect Tommy knows very little about keeping up a relationship. But what he does understand is seduction. Tommy knows how to entice a beautiful, high profile, (and often slightly crazy) woman to invite him into her boudoir. And we are talking about some very big names, including Carmen Electra, Pamela Anderson (married), Pink, Jenna Jameson, Jesse Jane, Heather Locklear (married), Kimberley Stewart, and Elaine Bergen (married).

How does he do it? Well, he once offered some advice in Men’s Health stating: “Dudes, mow the front lawn. Trust me, the right woman – fu** that, any woman – will appreciate it. So keep your pubes under control… and if you have back hair that your girl can knit a sweater up your spine, do something about it!”

Gerard Butler

Gerard Butler

If you’d sit down with Gerard (“Gerry” to any American who can’t pronounce his name correctly) and strike up a conversation about women, he’d likely tell you his secret to success has always been his handsome looks and lovable personality. And unlike Valderrama, he’d be quick to discount any rumors about the women he’s been with. In short, he admits to nothing, apologizes to no one, and lives by a motto similar to Popeye “I am who I am… I’m just Gerry”.

And while you’d likely never get his full resume of women just by asking, we’ve done the legwork for you. Gerry has hooked up with the likes of Ashley Greene, Jessica Biel, Laurie Cholewa, Jennifer Aniston, Cameron Diaz, Naomi Campbell, and Rosario Dawson. And he can’t even sit outside of a restaurant for 30 minutes without catching the attention of at least a dozen sexy nameless women. And if we were to get scientific about his tendency to lose interest in women quickly, we think that is best explained by this quote he shared to the Star several years ago: “You have to give up the good for the better.”

Female hypergamy results in a tendency for around 80 percent of a population’s females to mate with around the top 20 percent of available males. If the top 20 percent of males were prudes – say, only sleeping with one women throughout their life, the majority of women would have no satisfactory mating options. So, attractive male womanizers are actually doing a great service to women.”

-Reuben Rosado, Life Coach

John Mayer

John Mayer

“No, absolutely not,” replied Mr. Mayer when asked if he was a womanizer by Ronan Farrow of the Today show. However, Mayer would also tell anyone straight up, “I do all right,” when asked about his success margin at a singles bar. He also hates to be the ‘heartbreaker’ according to an interview in Playboy Magazine back in 2010. What does a dating resume look like from a man like this, you may be wondering?

His dating resume kicked off back in 2002 with Vanessa Carlton, followed by Jennifer Love Hewitt, whose ‘body’ was behind the lyrics, “Your Body is a Wonderland.” He began hooking up with Jessica Simpson in 2006, describing her sex as addictive as “crack cocaine.” Mayer moved to Minka Kelly in 2008 and then dated Jennifer Aniston for about a year before hooking up with Taylor Swift. Katy Perry spent some considerable time with him before rumors surfaced he was hitting it up with Demi Lovato.

He’s since had quite a falling out with Lady Alcohol, but he’ll be back.

Dan Bilzerian

playboy lifestyle

Not many men have a story about how they provoked their own heart attack using around 200 milligrams of Viagra (50 milligrams is the normal dose, in case you were curious). But he was in Las Vegas and he’d just met this really hot stripper, so why not, right? And everything ended happily, other than the lingering erection that had him on the line with the late, Michael Jackson’s, doctor – and well, there was also that second heart attack about 12 hours later. But this is just a typical day in the life of Dan Bilzerian.

Conquests: 16 girls in 12 days.

A life that also includes occasional film roles, exotic supercars, yachts, planes, automatic weapons, self-made bombs, professional poker status, training as a Navy Seal (he never made it due to his “bad attitude”), and an incredible beard. A beard that is so important to his charisma that he once turned down $100,000 (chump change) to shave it off. As to our best estimation, Dan’s greatest attribute as to being a worthy ladies’ man is also the $100 million he is currently estimated to be worth.

Gene Simmons

What is one of the best kinds of problems that a player can have? Answer: Forgetting just how many groupies he’s scored with. Was it 4,600? Or maybe more like 4,800 or 5,000, ponders Kiss frontman, Gene Simmons (father to Sophie Simmons). But don’t be fooled, he could have counted the exact number, as he used to take polaroid pictures to document each session. Unfortunately, rumor has it that his current wife, Shannon Tweed, made him burn most of his collection in a massive bonfire, so now he has only his memories – plus a few favorites we suspect he spared from incineration.

Claimed Conquests: 4,600 (and he says that number is probably a little low)

In Gene’s case, the quantity may have been a little higher on his priority list than quality, but that doesn’t mean he hasn’t had his fair share of Hollywood’s hottest women. We’re talking about such highlights as Bonnie Large, Liv Ullmann, Jessica Hahn, Linda Johansen, Diana Ross, Cher, and Katey Sagal. Depending on when you were born, this list may not impress you much, but allow us to remove any doubt – yes, these women were incredibly hot in Gene’s prime.

Simon Cowell

Here is a man who hijacked a bus with a literal ‘peashooter’ at the age of 12. He dropped out of school at age 16, partied with Playboy Playmates at age 50, and knocked up the wife of a good friend not long after. He owes some of his success to the over $250 Million (US) he has built up throughout his producing career.

The rest of Simon’s success as a Philanderer comes from his brass, honest, and direct approach to life. The kind of directness that can get a man fired from polishing Jack Nicholson’s ax on the set of Stanley Kubrick’s The Shining. But Cowell is not really the kind of guy to stay happy polishing trinkets unless it happens to be his teeth, his reflection on his Bugatti Veyron, or the tush of some young Playboy Playmate.

James Hunt

If you have never heard of James Hunt, just ask the 33 BA stewardesses he was rumored to have bedded before his world championship crowning at the 1976 Formula One race in Tokyo. They probably didn’t know much about him either, other than he was handsome, successful, one hell of a driver, and incredibly bold and confident. Wheaties may be coined the breakfast of champions, but in Hunt’s day, it was alcohol, cocaine, and sex – just not necessarily in that order (especially in Hunt’s case).

Claimed Conquests: 5,000 women

Hunt was discovered in a pit garage on the morning of the 1976 Formula One race with his overalls around his ankles with an unnamed Japanese girl. Sex on the “the go” was exactly how Hunt preferred it and is also the tool he used to sober himself up after a night of drinking and drugs. He usually followed this up with a good vomit and casual urination in front of the crowd of spectators, who’d cheer him on after he was finished.

Jack Nicholson

Jack Nicholson

When asked if he had any regrets to his life, Jack Nicholson casually explained, “You rarely regret anything—you did, but you might regret things that you didn’t do.” And when it comes to women and drugs, there are likely very few he didn’t do. “Jack”, as he liked to be called by the ladies, has described his interest in sex starting alone in the bathtub before the age of 8. He would later become known as “the most highly sexed [man],” to Kim Basinger, earning the nickname “Hot Pole” by Anjelica Huston.

Claimed Conquests: 2,000

Jack’s long list of Hollywood’s finest women, includes Candice Bergen, Kelly LeBrock, Diane Keaton, Margaret Trudeau, Janice Dickenson, Michele Phillips, and Rebecca Broussard. And while you might imagine that Jack had the last word at the end of each of these relationships, he would say, “In my long-term relationships, I’m always the one that gets left.” And to say that Jack is a womanizer, he would never deny it – but if you celebrated his life as a ladies man as a victory, he’d gladly remind you, as he told People Magazine in 1975, “The life of a gigolo always ends badly.”

John Holmes

A man of many legends, Mr. Holmes was said to have a manhood that reached 12.58-inches long, according to SCREW Magazine. According to the man himself in an interview with Hustler Magazine, he’d had sex with over 14,000 women and men before his death in 1988 (he was only 43 years old).

Claimed Conquests: 14,000 (2,000-plus from roles in porn film)

But as all legends go, these numbers often dwindle once some of their legends wear off. His ex-wife claimed his manhood to be more along the lines of 10-inches, and that was from the night she witnessed him measure it for the first time. The conversation with himself went something like this: “It goes from five inches all the way to ten. Ten inches long! Four inches around!” An expert porn historian (we didn’t know there was such a thing), has since foiled his legendary 14,000 lays, claiming his sex count was more likely 3,000-plus.

Scott Baio

Scott Baio

Scott has eluded to sleeping with one-thousand women, but truth told, he probably lost count somewhere back in his Joanie Loves Chachi days. He made his big-screen debut in Bugsy Malone when he was only 15-years-old. This success would eventually lead him to a popular role of Charles “Chachi” Arcola in the late 70’s and 80’s television classic, Happy Days. It was here that Scott would make his first enemy of the female nation, Miss Erin Moran, also known by her character, Joanie Cunningham. Erin was Scott’s first temptation, and she claimed in later interviews that Scott’s equipment was rather ‘petite’. While obviously meant to tarnish his legendary philanderer status, it never seemed to affect his ability to pick up new women.

Claimed Conquests: 1,000

Scott was quoted on the Howard Stern Show as “going ugly” on occasion, or in other words going home with the less attractive women when he was too tired. He told Howard that this was his way of “giving back” to those less fortunate. Scott was particularly fond of Playboy playmates and was informally banned from the Playboy Mansion when discovered by Hugh Heffner as having bedded an entire year’s worth of Playmates. And not just individuals mind you, but each consecutive Playmate of the month for that entire year, one after the other. Nobody disrespects “The Heff” like that!

Hugh Hefner

Hugh Hefner

Hugh Hefner started his infamous magazine over 60 years ago, but before then, he had remained a virgin until the age of 21. But Playboy became much more than just a paycheck – it was a lifestyle. He has indulged in almost every sexual experience possible, including one woman, multiple women, celebrities, a threesome with his own brother and sister-in-law, and even had another man (‘just to see what it was like’). Hefner claims he’s bedded just about every woman who’s graced Playboy’s cover. It wasn’t uncommon for him to have slept with at least 11 out of the 12 playmates of each month. That kind of mojo gained him his own subspecies of rabbit, the Sylvilagus Palustris Hefneri.

Claimed Conquests: “Over a thousand,” and that number may seem low, but he explains it is because he was always ‘faithful’ to his occasional marriage.

One urban legend states that from 1955 to 1979, Hefner would use a certain number of stars around the “P” in his magazine. This was his inside rating system of the featured playmate which either described her attractiveness, the number of times he bedded her, or how good she was in bed. During Hefner’s glory years, he hooked up with such prominent bombshells as Donna Mitchelle, Marilyn Cole, Shannon Tweed, Lillian Muller, Patti McGuire, Brande Roderick, Barbi Benton, Karen Christy, Sondra Theodore, and Carrie Leigh.

Mick Jagger

Mick Jagger

Out of all the women Jagger has had, the one who he could never quite land, no matter how hard he tried–was Angelina Jolie, according to his biography. But he was also handicapped at the time, being married to model, Jerry Hall, and with kids. And we mean that quite literally, in that Hall was standing nearby with their two children as he was putting the moves on her. But that kind of behavior was normal for Jagger, who even tried to ‘jump’ one of his wife’s friends on their wedding night.

But Jagger never let marriage stop him from racking up conquests. While married to Bianca Jagger from 1971 to 1979, Jagger was also linked to encounters with Carly Simon, Linda Ronstadt, and Mackenzie Phillips. While married to Jerry Hall, from 1990 to 1999, he enjoyed the temptation of Carla Bruni, Valerie Perrine, Uma Thurman, Nicole Kruk, Daryl Hannah, and Miranda Guinness. Now in his 70’s (or is it 80s), Jagger has had over 80 ‘documented relationships,’ but has, unfortunately (and most likely, conveniently) lost count of the one-nighters.

Bill Wyman

Bill Wyman

Over the course of three months, the Rolling Stones Bassist, Bill Wyman, could notch off 265 women. That’s somewhere around two per night, not including the couple nights upwards of four were on the menu. “They helped me get over the boring times,” Wyman would tell the media. “It was better than drugs because you couldn’t OD on it.”

Claimed Conquests: 1,000

Unlike many other skirt chasers on this list, Wyman did not rely entirely on his fame and fortune to get women. As a matter of fact, a big part of his later ‘fame’ was his amazing success rate with women. And when asked what was his secret, Wyman has simply said, “A friend said if you ever want to be successful with women treat them all like ladies–whether you think they are ladies or not, treat them all very respectfully and nicely.”

David Lee Roth

“I slept with every pretty girl with two legs in her pants,” said David Lee Roth (a.k.a. Diamond Dave) as he attempted to sum up his love life in as few words as possible. Beyond being apparently impartial to one-legged women, this philosophy aided him and “little Elvis” (every Casanova should have a name for his penis) to amass hundreds if not thousands of notches to his bedpost over his touring years. But Dave did get a little help from his road crew, also known as “Diamond Dave’s Bonus Program”.

Claimed Conquest: 5 girls at the same time.

Rather than an extra dollop of whip cream on your yogurt sundae, Dave’s program revolved around finding him the best groupie from each show. At every concert, Dave would hand out five backstage passes to every crew member (let’s call them ‘unsung wingmen’) who would pass them out to eligible bachelorettes. The hottest groupie who found her way into Dave’s arms for the night would land that crew member an easy $100.

Steven Tyler

Steven Tyler has summed up his legacy as a philanderer in eight words: “Don’t get f*ckin’ married – Lie till you die.” His first bit of advice comes from the countless divorces he dished out, and the second probably helped him through the backlash of each of them. Steven claims to have never been turned down by a single woman throughout his playing years, noting his success to being a combination of persistence, rhythm, sensual presentation, and memorizing poetry.

Claimed Conquests: Tyler claims he was too high at the time to count.

Here is a classic pro tip from Steven to the budding Don Juan. When on the road and cheating, always give yourself 10 days of faithful time before you get back home. This accomplishes two things. It minimizes the chance of spreading venereal disease to your committed partner, and two, it ensures you will have a “full cup of chowder” when you do get together (suggesting you’ve been faithful, in theory (Tyler’s theory, to be clear).

Rick Flair

“Do you want to ride Space Mountain?” Ric Flair would ask women, referring to the roller coaster residing within his tight underpants. And starting from the age of 15, Ric claims to have been shoveling through about 3.6 women per week (pardon the half-woman).

Claimed Conquests: 10,000 women

But that’s not all. Ric also claims to have been servicing himself somewhere around twice a day (rain or shine). So, allow us to punch out the numbers for you. That adds up to around 10,000 women and 22,000 knuckle sessions.

Lemmy Kilmister

Lemmy

Kilmister is already a legend among seduction masters, having been crowned among the top 10 “Living Sex Legends” by Maxim magazine. “I’ve been screwing since I was 15,” Kilmister told Maxim in an interview. “[1,000 women] That’s pretty reasonable after that many years.”

Claimed Conquests: 1,000

And after we sat down and did the math, we figured that he’s been sleeping with roughly one and a half women per month, which is something that any man could strive for. “I could’ve done more if I’d tried, I guess,” Kilmister pondered during an interview with Spin. And suddenly, 1.5 women sounds more impressive now that we know he wasn’t even trying.

Julio Iglesias

Julio Iglesias

“Me, I don’t have numbers,” says Iglesias when asked about his rumored 3,000 conquests over his lifetime. “[But] you cannot go from door to door saying, look it’s not true.” Especially when you are a bit proud of your legacy. And why shouldn’t he be? He knows exactly what to say to the ladies. Like father, like son–Julio is also the son of a well-known gynecologist who fathered his last child at the age of 90, so it’s in his genes. 

Claimed Conquests: 3,000 (but he’s not counting)

During his first marriage to Isabel Preysler, Iglesias is rumored to have stepped out with Diana Ross, Priscilla Presley, and Bianca Jagger. He now has eight kids with Dutch model, Miranda Rijnsburger, and since he is nowhere near the age of 90–we can assume he’s far from getting out of the baby-making business.

Willie Nelson

Willie Nelson

“A hard d*** has no conscience,” Nelson has offered up as the excuse for why his first marriage was doomed from the moment he learned that he could sleep with beautiful women without even working to get them. But that’s the life of a successful musical artist. Willie’s legend climaxed in 1991 when he told Rolling Stone magazine that the only true story he ever read about himself was that he once had sex with a woman for nine hours, and accomplished a backward somersault in mid-action. 

Nelson later admitted that he didn’t actually remember any portion of that nine-hour sex marathon. But considering that he couldn’t remember, he also figured, “it might’ve [happened].” For all Willie’s success with women (both imaginary and real), we wouldn’t classify him as a true Casanova. And this is because, despite all the women he’s bedded, it is ‘Marie Jane’ that has consistently proven to be his true obsession.

Magic Johnson

A lot of magic happened both on the court and in between the sheets when Magic Johnson was in town. But as good as this Casanova was, most sessions did not come completely free, as it isn’t uncommon for NBA players to ‘pay’ for these nights with a pair of autographed sneakers or similar. Some of the most beautiful NBA roadies own closets full of sneakers to which they covet as trophies for their hard work.

Conquests: 1,000

Magics lifestyle changed drastically in 1991 when he found out that he had contracted AIDS from one of these evenings. And the timing couldn’t have been worse, having just been hitched to his new wife, Cookie, and was within months of being a first-time father. After telling his wife the grim news, his next step was to lock himself in the bathroom and proceed to call as many of the previous flings he could remember. It was a long, dark night, but the real magic to this story is that Johnson is still married to Cookie, and continues to flourish with good health.

While womanizers may come across many women, it only takes one to inhibit them from moving on to the next target. These women are able to appeal to playboys by offering the adventure, excitement, and temptation of many women.

– Caleb Backe, Health and Wellness Expert for Maple Holistics.

Ilie Nastase

Ilie Nastase

You don’t earn a name like Ilie “Nasty” Nastase by singing love songs in a girl’s backyard while holding a ghetto blaster up to the stars. You earn it by winning 100 professional tennis titles (women like titles). You earn it by acting like a jackass on the court, (women like a charming jackass). You earn it by wearing a military uniform (Ilie has several in almost every color you could imagine). And you earn it by being bestowed by Maxim magazine as one of the Top Ten Legends of Sex in the world. Not to mention, Nasty also boasts some pretty large hands just in case anyone had any question about the size of his manhood. 

Claimed Conquests: 2,500 based on his autobiography, although he has since dumbed the number down to 300 to 400.

For his 69th birthday, Ilie teased to Daily Mail: “I have to have a fun birthday invitation: girls only, no partners. It will be fun. I like fun.” Yes, we know that you do, Nasty. He has been married four times, including his fourth wife, Brigitte, who Ilie noticed on television (she is a famed Romanian model). And Ilie’s best advice for the up-and-coming adulterer: “The rooster should attack the chicken. But when you play and win all the time, it’s difficult to chase.”

Engelbert Humperdinck

Engelbert Humperdinck

“I’ve had more paternity suits than casual suits,” casually claims the 80-plus-year-old singer. And in case you don’t know much about Mr. Humperdinck, he has lived the majority of his life in casual suits, and he openly admits that his wife of 50 years has always known about his affairs. But it’s okay because he plans on spending his remaining years making up for it.

Conquests: 3,000 by ‘casual’ estimation

And what was his secret to getting away with running around on his wife, you might be wondering? For one, he calls her a “wonderful lady” these days and also “very intelligent”. Two, he now calls her several times a day to talk (just because), and three, because, “[She] knew deep down that, whatever I did, it wasn’t serious.” She sounds like a keeper.

Warren Beatty

Warren Beatty

Warren is unquestionably one of the greatest womanizers of all-time. He is not only known for his quantity of women but also the quality. Some of his famous conquests include Joan Collins, Cher, Daryl Hannah, Janice Dickinson, Elle MacPherson, and the “material girl” herself, Madonna (she has appeared a lot on this list). Warren was known to be an insatiable lover. Joan Collins claimed in interviews he would need servicing three or four times per day. It was so frequent, she recalled moments where he conducted business over the phone while having sex with her. Not long after these interviews hit mainstream, his own sister, Shirley MacLaine, teased that she’d like to have sex with him just to see what all the hub-bub was about.

Claimed Conquests: Over 13,000, according to his biographer, Peter Binkind.

Unfortunately, his sexual prowess was also tied to a sexual ADD, which left him always looking to mount a new expedition over unchartered territory. In his prime (1970’s), Warren had sex with approximately 12.7 women per day. Flashing these sorts of numbers, you’d think he must have been taking appointments. In fact, it’s been eluded that is indeed how he conducted his personal affairs. If he was at a party and saw a woman he liked, he’d walk boldly up to her, blurt out, “What’s Shaking Babycakes,” make a few suggestive comments, drop his room key in her hand, and saunter off. When asked later in life why he’d never married (prior to his 1992 marriage to Annette Bening), he said, “Just because you need a quart of milk doesn’t mean you have to go out and buy a whole cow.”

A womanizer is capable of being in a relationship as long as that is what he wants. No matter a man’s reasoning for treating women like throwaways, whether because it’s fun for him or it’s the result of some deeply rooted issue, a man can choose to change his ways if he longs for a relationship bad enough. It probably won’t be easy and he might mess it up at first, but there’s light at the end of the tunnel if he stays committed to being a better man.”

-Heather Ebert, Relationship expert at WhatsYourPrice.com

Eric Clapton

Eric Clapton

Like many rock legends, Clapton searched for himself at the bottom of countless whiskey glasses, and between the sheets of multiple one-night-stands. “I used to identify my self-esteem with sex,” remembers Clapton. “I’d get drunk first, and then have to be kind of guided through it.” He would eventually find love in glamour model, Pattie Boyd (the girl behind his song, “Layla”). She was spoken for at the time by his close friend and member of The Beatles, George Harrison. One night, Clapton jokingly announced at a party to George, “I have to tell you, man—I’m in love with your wife.”

Claimed Conquests: Presumably over 1,000

George responded characteristically with, “Whatever you like, man. You can have her, and I’ll have your girlfriend (model, Cathy James).” And so the two men swapped women and remained good friends. Unfortunately, Clapton’s marriage to Pattie was constantly on the rocks, ending in 1988 due to infidelity and a long history of drinking and abuse. This left Clapton looking for more esteem builders, from which he’d recruit the likes of Sharon Stone, Michelle Pfeiffer, Naomi Campbell, and Sheryl Crow. Clapton has only one regret in his old age, “Women [don’t] look back anymore when I look at them.”

Wilt Chamberlain

wilt-chamberlain

“Wilt the Stilt” was one of the greatest basketball players the world has ever known. Standing 7′ 1” and 300 lbs, he dominated the NBA in scoring, rebounding, and durability. On March 2, 1962, he scored a record 100 points against the Nicks. Later that evening he would celebrate by adding a few additional notches to his bedpost. In his autobiography, A View From Above, Wilt claimed he’d had sex with an estimated 20,000 women (1.14 women every day, since the age of 15). He later admitted to his on-and-off girlfriend, Lynda Huey, that the number might have been fudged a bit, saying, “What’s a zero between friends?”

Claimed Conquests: 20,000 (maybe an extra zero thrown in for good measure)

Wilt’s personal record was 23 different women over 10 days. As his lawyer Seymour “Sy” Goldberg put it, “Some people collect stamps, Wilt collected women.” His personal life became the source of much criticism, skepticism, and jokes in the early 80s. His million-dollar mansion in Bel-Air, California, was famous for miniature Playboy Mansion-like parties in which he lived out his fantasies of having sex with multiple women. He had a special playroom built with a wall-to-wall waterbed for such occasions. However, some of Wilt’s comments would elude regret later in life. “I have learned in my life,” said Wilt before dying in 1999. “I’ve found—that having one woman a thousand different times is much more satisfying.”

Charlie Sheen

charlie sheen

With links to such beautiful women as Denise Richards, Ashley Dupre, Kelly Preston, Winona Rider, and Jess Impiazzi, Charlie is what you’d call somewhat of a natural-born wolf. This is a man who lives for sex, and will even pay for it if the moment calls for it. But don’t give the word ‘prostitute,’ too much thought, as the actor also claims, “I don’t pay prostitutes for sex – I pay them to leave.”

Conquests: 5,000 (a good portion prostitutes)

Ever since his AIDS diagnosis went social in 2016, Charlie has kept up his positive spirits saying that if sex becomes unavailable due to his predicament, “I’ll spend more time hanging with my parents.” And his parent’s response to that quote was simply, [no comment]. This is not the kind of end a philanderer has in mind for himself, but sh*t happens.

King Juan Carlos of Spain

According to one high-ranking Spanish army officer, the one woman King Juan Carlos spent the least time with was… Sophia, his wife. His online dating profile would have likely read, “Married, but prefers hunting, skiing, boating, and bedding other women.” However, King Carlos was a man who preferred to fly under the radar as a swinger, which was difficult for a man of 6 foot 5 inches and well over 200 pounds.

Claimed Conquests: 5,000 women (4 per week on average)

The first author to call out the King claimed his conquest count to be at 1500, but Carlos was still on the throne (had a higher approval rating), and that author likely preferred his head on top of his shoulders. Author, Martinez Ingles, has since set the stage at 5,000 women and 20 illegitimate children. One of his most public attempts as a Romeo was his effort to swoon, England’s Princess Diana in the late ’80s. But she was in good company with many other high-profile singers and actresses at the time.

Fidel Castro

Castro was a man of many impressive numbers. He lived to the over-ripened age of 90-years-old. He amassed somewhere around $500 million (but claimed none of it to be his own). He survived near 600 assassination attempts and slept with an estimated 35,000 women (2 per day for the majority of his political career).

Claimed Conquests: 35,000 (2-3 women per day for over 40 years)

But we can’t credit Castro for pulling in these women in using his magnetic personality. Instead, his legacy paints a picture of a man blowing smoke in these ladies’ faces, and leaving his boots on during the deed. He relied on his personal bodyguards to scan the beaches of Cuba looking for volunteers to become his next afternoon and evening ‘delights’. But considering the 35,000 women he laid, he also claimed this next impressive number – and that is, he only fathered less than a dozen children. You do the math.

King Fatefehi of Tonga (AKA Pimp Daddy)

It is one thing to have slept with over 35,000 women, and a completely different honor to be able to claim them all as virgins. King Fatefehi was the king of Tonga from 1970 to 1984, and with that honor, he bestowed himself the privilege to deflower every woman upon entering the age of womanhood within his kingdom. 

Conquests: Between the years of 1770 and 1784, King Fatefehi apparently deflowered 37,800 women (that’s 7 virgins per day, for 14 years).

And while we can’t give Fatefehi any credit for the quality of these women, his smooth approach, or how polished his pickup lines must have been. We can say that he has sampled probably the largest amount of virgins in history, especially considering most men are lucky to come across one in their lifetime.

We know from clinical practice that men from warmer countries (i.e. Italy, Mexico) tend to be more sexually open-minded as they are exposed to female beauty more readily than men from colder countries. This explanation might appear ridiculous at first, but from a psychological perspective – warmer weather makes it easier for people to wear less clothing, thereby exposing our bodies to others; men notice that (men are visual beings) and that exposure to the physical bodies of women makes them more receptive to further exploration.”

-Damian Sendler, Sex Doctor

Sultan of Brunei (Hassanal Bolkiah)

If the married adulterer could build his ideal mansion, it would look something like the 1,788 room, 110-car garage palace the Sultan of Brunei currently resides in. It is here that the Sultan can disappear into any wing where he and his brother, Prince Jefri (he instructs the girls to call him “Robin”), take part in frequent underage sex parties. These parties also expand to the waters from time to time on his brother’s 152-foot yacht, appropriately named “Tits”.

And while King Fatefehi was limited to the women of Tonga, the Sultan of Brunei employs a global network of men and women whose job is to procure the most beautiful women around the world and bring them to their parties. It is quite common for Prince Jefri to place ‘orders,’ pointing at a glossy magazine cover and saying, “I want that one.” And then a team of workers is tasked to find that fashion model or Miss Universe winner, dump a pile of money at her feet, and then fly her out to the palace where she is practically given a number, instructed to wait in a room at the palace for weeks/months until she is eventually ‘sampled’ by one (or both) of the brothers.

Lord Byron

As an English (British) poet in the 19th Century, Lord Byron was the narrator of Don Juan and also held a leading role in the Romantic Movement. “She walks in beauty, like the night,” Byron wrote. “Of cloudless climes and starry skies.” And it was this kind of language that gave him high scores among most women.

Conquests: 250 women in one year.

Rumor has it that he once slept with 250 women in a single year, and captured these moments with locks of pubic hair in which he stored in sealed individual envelopes. And he not only a lover of women, but also men, his half-sister, and a couple of distant cousins (for good measure).

Jacobo de Grattis “Don Juan

Don Juan may be a fictional character, but if scholars were to reference his life to an actual person, a nobleman from Modena by the name of Jacobo de Grattis would make the closest comparison. Also known as the “Caballero de Gracia,” Grattis’ had a way with women that led to his reputation as a born seducer and sex addict. Like many of the modern Don Juan’s above, Grattis lived out his final years repentant of his bad behavior, which in the 1500s meant dedicating his life as a priest.

Umberto Billo

Thus far we have proven that you either have to be famous, powerful, influential, or incredibly wealthy to become a notable Casanova. But that is just not true. Umberto Billo is a hotel porter in Venice who is rumored to have bedded a massive number of women throughout his luggage toting career. His secret, as per his own words: “I stood at the hotel entrance and held the door open as they (women) walked in – a glance, a small compliment – that was all it (they) needed.”

Claimed Conquests: 8,000 women

Umberto was fired from the hotel at age 45 because he was proving to be too tired to haul luggage in between his sexual activities. He later settled down (let us call it retired) as a psychiatric nurse, where he reported to have downgraded to only one new woman per night.

Giacomo Casanova

At last, we have come to the man himself, Giacomo Casanova. A brilliant lover and seducer he may have been, but he was also a villain, rapist, and a bit of a peacock. As a sickly child, Casanova writes, “She aroused the most intense emotions in me,” about being bathed by a young girl at the age of nine years old. He would go on to lose his virginity to two sisters with which he was sharing the same bed with. To offer more clarity to this pivotal moment, these were two sisters of the woman he was calling his sworn love at the time. And according to his memoirs, he was never able to tell which sister he finished with first before rolling over to the other one.

Claimed Conquests: 120 by his memoirs

From this point on, Casanova flamed the passions of many flings, including women of nobility, eunuchs, nuns, and even his own daughter during a threesome with her mother. “I have never been able to understand how a father could tenderly love his charming daughter,” recounts Casanova. “Without having slept with her at least once.” Casanova never suggested any guilt or remorse for the acts of sex and seduction he committed, both consenting and forced, writing, “I was born for the sex opposite of mine – I have always loved it and done all that I could to make myself loved by it.”

Men become womanizers for simple reasons: they don’t know the difference between excitement and happiness, and they regard women as underlings or objects instead of relating to them as equal human beings. Often, the womanizing behavior represents a way for a man to compete with other men for status and prestige. The woman’s body is like a football field on which a man can “score” in his competition with other men. These problems reflect a lack of emotional maturity, and they make true intimacy impossible. It is theoretically possible for a man to outgrow this problem. The science fiction movie Cherry 2000 dealt with a man who learned how to appreciate a female human being:”

-Laurie Endicott Thomas, MA, Author of Don’t Feed the Narcissists! The Mythology and Science of Mental Health

There are really only two valuable commodities that a player needs – style and confidence. This is simply because almost all women find handsome men interesting, and confident men sexy. Keep in mind, these are relatively short-lived advantages, considering that women receive very little pleasure from a man’s perceived value and success, outside of bragging rights to their girlfriends.

The ultimate Casanova should possess both a strong short game and long game because, in the end, every man’s goal should be to find happiness with one woman. And the reason that many fail over the long haul is they fail to take interest in what makes a woman happy. What grabs a woman’s attention in the beginning, is not the same as what keeps her true until the end.

Let’s lay this out as plain and simple as it gets. Maintaining a woman’s love and interest requires three simple (but difficult) things: The ability to listen, the sense to encourage her when she needs (asks for) it, and the drive to inspire her to find true happiness.

Read More
How to Pickup Women – With or Without Confidence
Dating Tips From Women – Meeting, Mating, and Mood Music
How to Seduce Women – What Most Dating Coaches Get Wrong
Man’s Guide to Dating – When She’s Not into You
Improve Your Game By Ditching Dating Approval Addiction
Top 4 Traits Women Look for in a Man
How to Get Out of the Friend Zone
9 Tips to Become Instantly Attractive to Women
What You Can Tell By Looking at a Woman’s Legs
12 Ways to Flirt With Women Using Only Your Body Language
20 of the Most Aggressive Pickup Lines Men Should Know
How to Appear Sexier to Women
5 Best Ways to Ask Any Woman for a Date


About Dr. Eric J. Leech

Eric has written for over a decade. Then one day he created Urbasm.com, a site for every guy.



About Dr. Eric J. Leech

Eric has written for over a decade. Then one day he created Urbasm.com, a site for every guy.