The Ladies’ Man Trope, Explained

The Ladies’ Man. He’s charming, he’s slick, and he just might end up breaking your heart. How has he gotten away with this for so long? Are his good looks and magnetic personality worth the pain he might leave you with? Watch this video for our deep dive into The Ladies’ Man.


The ladies’ man: Women want him. Men want to be him. This archetype of the handsome, charming ladykiller has worked his wiles across centuries of literature, film, and television.

Although the ladies’ man may have changed up his game over the years, there are a few things that will always identify him:

He’s almost supernaturally charming, with a charisma that puts his targets at ease. He’s extraordinarily sexual, focused at all times on his next conquest—and confident of his own prowess. He’s unattainable—which only makes him more attractive to women and the envy of every other man. He’s also dangerous. Falling for the ladies’ man often ends with broken hearts and hurt feelings—if not something more sinister. More than anything, the ladies’ man is defined by his relentless drive to pursue women. But in more recent years, pop culture has increasingly asked why he is the way he is, and what he’s really chasing after.

Frank Mackey: “Mommy wouldn’t let me play soccer and daddy hit me. So that’s who I am? That’s why I do what I do? - Magnolia

Here’s our take on what makes the Ladies’ Man, how he’s evolved over time, and whether it’s possible for this most incorrigible of characters to ever change his ways.

The Evolution of the Ladies’ Man

The ladies’ man is as old as storytelling itself. Early civilizations believed in the incubus, a demon who had sex with sleeping women to steal their life force. In ancient Greece, the god Zeus was the ultimate ladies’ man, sleeping with goddesses and mortals alike—sometimes even transforming himself into an animal just to get a little more action.

In the 17th century, the ladies’ man became known by another name: [chyron] Lothario, after the playboy character in Miguel de Cervantes’ 1605 novel, Don Quixote. In 1630, playwright Tirso de Molina gave the world “Don Juan,” a shapeshifter who could change his appearance and language to seduce any woman he wants. And in the 18th century, an Italian libertine named Casanova became so infamous for his liaisons that his name, too, would become synonymous with “womanizer.”

These ladies’ men were often regarded as wicked: Casanova was jailed for blasphemy and affronts to decency. Don Juan was portrayed as a devil—Mozart’s opera version, Don Giovanni, ends with him literally being dragged to hell. But as social mores loosened, the ladies’ man became a more romantic figure, especially in early film.

Rudolph Valentino played a series of dashing, heroic ladykillers in the 1920s, earning him nicknames like the Latin Lover. The passionate, noble “rogue”—as played by Douglas Fairbanks in movies like The Mark of Zorro and The Thief of Baghdad—quickly became Hollywood’s dominant role for leading men. With 1926’s Don Juan, starring John Barrymore, and later 1948’s The Adventures of Don Juan starring Errol Flynn. With Errol Flynn’s The Adventures of Don Juan, even the most famous sinner in literature was transformed into a swashbuckling hero.

For Fairbanks and Flynn, their roles were only enhanced by their actors’ off-screen reputations as womanizers. The same could be said of two of the leading ladies’ men of the 1930s. Clark Gable—described as an “unshaven he-man” by Variety—broke out with his rogue-ish turn in 1932’s Red Dust. Gable’s manly swagger and seductive way with words led directly to his most famous role, Rhett Butler in Gone With the Wind.

Rhett Butler: “You should be kissed, and often, and by someone who knows how.” - Gone With the Wind.

That part was turned down by fellow ladies’ man and one of Gable’s biggest rivals, Gary Cooper, who’d established himself as—in the words of critic Anne Helen Peterson—the kind of man who was “volatile, full of honor, a bit of a secret romantic, yet still and always the hero.” Like Gable, Fairbanks, and Flynn, Cooper only enhanced his reputation by being, as Peterson wrote, “one of the most notorious philanderers in Hollywood.”

In the 1940s, amid the anxiety and alienation of World War II, this romantic ideal of the ladies’ man retreated into the shadows of film noir, eclipsed by a different kind of masculine icon — Humphrey Bogart’s world-weary cynic who nevertheless proves irresistible.

Ilsa Lund: “What about us?”

Rick Blaine: “We’ll always have Paris.” - Casablanca

In the ‘50s, it was the soulful, wounded men played by Marlon Brando and James Dean who captured hearts, not the “wealthy playboys” portrayed by Cary Grant or Rock Hudson. For a moment, the “ladies’ man” seemed out of fashion. But then came film’s most famous ladies’ man. Introduced in 1962’s Dr. No, the secret agent 007, first played by Sean Connery, was handsome, debonair, deadly with a gun, and with a quip…

Honey Rider “Looking for shells?

James Bond “No. I’m just looking.”- Dr. No

… and of course, never misses with women. The New York Times described James Bond as wish-fulfillment—a man “doing everything (and everybody) that an idle day-dreamer might like to do.” With his liberated lifestyle and charged libido, Bond came to embody the spirit of the swinging ’60s.

With the rise of blaxploitation, African-Americans finally got their own ladies’ men—and films like 1971’s Sweet Sweetback’s Baadasssss Song quickly made up for years spent neglecting black sexuality. The liberated ladies’ men of blaxploitation were highly sexualized and almost superhuman in their prowess.

But amid the sexual liberation and second-wave feminism of the ‘60s and the ‘70s, we also started to see the dark, empty side of the ladies’ man. Michael Cain’s Alfie’s philandering ways leave him utterly alone.

Alfie: “What’s it all about? You know what I mean.” - Alfie

In Saturday Night Fever’s Tony Manero may be a strutting disco king, but the women in his life see right through him. Warren Beatty’s hairdresser in Shampoo can have any woman, but not what he really wants. Increasingly, the ladies’ man seemed less sexy than sleazy—and a little bit sad.

By the ‘80s, pop culture seemed to be actively punishing ladies’ men like Richard Gere’s hustler in American Gigolo, whose lack of human connection makes it easy to frame him for murder or St. Elsewhere’s promiscuous Dr. Bobby Caldwell, who has his face slashed by one of many one-night stands before he contracts HIV.

The ‘90s ladies’ man often hid behind a veil of hipness, or brooding disaffection.

Troy Dyer: “I may do mean things, and I may hurt you, and I may run away without your permission, and you may hate me forever.” - Reality Bites

But he was also a joke—like Austin Powers’ James Bond spoof or, of course, Saturday Night Live’s “The Ladies Man.”

The “ladies man” had become a cliche. He was a parody—a postmodern construct to be analyzed or imitated. But by the turn of the millennium, the joke wasn’t funny anymore. Increasingly, the ladies’ men that we met seemed joyless and lost. His sexual pursuits were now seen as a cover for emotional immaturity. The ladies’ man might appear confident on the outside—but what was happening on the inside?

I Know Your Type: The Psychology of The Ladies’ Man

While the ladies’ man would seem to have only one thing on his mind, his motivations aren’t always the same. As author Betsy Prioleau details in her book, Swoon: Great Seducers and Why Women Love Them, there are several different types of ladies’ man, each with unique personas, techniques, and psychologies. The most common is what Prioleau calls the “Darwinian Alpha Male”. Handsome, physically strong, and typically wealthy, these evolutionary studs represent a primal form of attractiveness that the anthropologist Edgar Gregersen says is “bound up with social status, or skills, strength, bravery, prowess, and similar qualities.”

Vesper Lynd: “I just want you to know that if all that was left of you was your smile and your little finger, you’d still be more of a man than anyone I’ve ever met.” - Casino Royale

James Bond is the quintessential alpha, although he has plenty of company, from the billionaire playboys Bruce Wayne and Tony Stark to Ryan Gosling’s master pick-up artist in Crazy Stupid Love. Gosling’s character is also an example of type 2 of the Ladies’ Man: the “Player Seducer”. He hunts women like a soldier, using “bravado, flak, and precision strikes”—often in the form of a good line.

Jack Jericho: “Did anyone ever tell you that you have the face of a Botticelli and the body of a Degas?” - The Pick-Up Artist

His methods are deliberate and pre-scripted. How I Met Your Mother’s Barney Stinson has even compiled a Playbook of all his schemes to land women—hacky lines, complex ruses, even elaborate costumes.

A darker form of the ladies’ man is the “Satanic Seducer”, whom Prioleau describes as a “cold, calculating sexual profiteer.” Armed with a “sinister leer” and “lethal charm.” These men seduce women as a game, out of arrogance, or even malice.

Sebastian Valmont: “I have no intention of breaking down her prejudices. I want her to believe in God and virtue and the sanctity of marriage, and still not be able to stop herself.”- Dangerous Liaisons

Lastly, there’s thePathologic Woman-Pleaser.” Narcissists, sociopaths, and sex addicts, they are “fixated on women through an array of mental maladies,” lacking empathy and conscience. They can be charming, like Mad Men’s Don Draper, or unsavory, like Charlie Sheen’s character in Two and a Half Men. But they are united by their relentless pursuit of sex, and their inability to form genuine attachment—or to ever be satisfied—because in the end, it’s only about themselves.

Don Jon: “There’s only a few things I really care about in life. My body…my ride… girls…my porn.” - Don Jon

While not every ladies’ man is outright disturbed, there is usually something about the character that’s flawed or damaged —some void they are always trying to fill with women. That void stems from fear: The ladies’ man is afraid of being vulnerable, so he doesn’t allow himself to get too attached. How I Met Your Mother even gives the ladies’ man an origin story, where Barney’s hard-hearted womanizing stems from getting his heart broken as a youth which leads him to conclude that women don’t want sweet, genuine guys; they want cruel, rich suits.

More often than not, the ladies’ man can only find true fulfillment by learning to love himself. But getting to that point might take changing his focus from women plural to woman singular—and finding the right lady.

Taming the Ladies’ Man

Even for the worst of ladies’ men, redemption is never completely out of reach. Most of these characters end up reformed—frequently by uniting with that right woman. In recognizing “The One,” they finally see how their endless pursuit of empty sex has only left them feeling empty. And they realize that what they’ve really been searching for, all along, is someone who makes them feel more than just fleeting, physical pleasure. But even if individuals can grow out of this phase, can there be redemption for the ladies’ man as an archetype? Our culture has shifted dramatically in recent years, moving away from the “boys will be boys” attitude that once regarded the ladies’ man as an amusing, romantic, aspirational character, and excused much of his worst behavior.

In the MeToo era, the tactics of the ladies’ man seem far more creepy than charming, and his objectifying, predatory attitude toward women is difficult to overlook.

Barney Stinson: “The only reason to wait for sex is if she’s 17 years, 11 months old.” How I Met Your Mother 1x14

In 2015, Daniel Craig said of his character—and ladykiller—James Bond, “Let’s not forget that he’s actually a misogynist..” Breaking with tradition, Craig has even refused to call his onscreen love interests “Bond girls,” emphasizing the way recent Bond films have “surrounded him with very strong women who have no problem putting him in his place.”

James Bond: “You don’t think this is a very good plan, do you?”

Vesper Lynd: “So there is a plan?” - Casino Royale

The ladies’ man needs to realize that the game has changed. Still, if even James Bond can mend his ways, maybe, just maybe, there could be hope for all those other lotharios, Don Juans, and Casanovas as well.

Works Cited

Petersen, Anne Helen. “Scandals of Classic Hollywood: That Divine Gary Cooper.” Medium, 6 June 2012.

Crowther, Bosley. “The Screen: ‘Dr. No,’ Mystery Spoof: Film Is First Made of Ian Fleming Novels Sean Connery Stars as Agent James Bond.” The New York Times, 30 May 1963.

Gregersen, Edgar. Sexual Practices: The Story of Human Sexuality. Franklin Watts, 1983.

Prioleau, Betsy, and Elizabeth Stevens Prioleau. Swoon: Great Seducers and Why Women Love Them. WW Norton & Company, 2013.

Sturm, Rüdiger. “Daniel Craig on James Bond.” Red Bull, 11 July 2017.

“Red Dust.” Variety, 31 Dec. 1931.