10 Most Notorious Womanizers in History

Don Juan may be the original lady-killer, whose breeches no woman could resist, but he was a fictional lothario whose exploits were bound to the stage, or the libretto, or the page; or, perhaps, if we can find ourselves once again in this post-feminist, enlightened age, to the reveries of women desirous of a little… action. And though he has lent his name to any man who too keenly makes the fairer sex his prey, his adventures have been long outdone by the living.

Genghis Khan (1162-1227)


In fact, centuries before Don Juan first set hearts aflutter in Tirso de Molina’s 1630′s play El burlador de Sevilla y convidado de piedra, Mongolian warlord and disreputable dictator, Genghis Khan, was lending an unsettling gravitas to the term ‘lady-killer’. Though he is remembered today for conquering a people and founding an empire, his sexual conquests were no less devastating. The tyrant’s fondness for a fertile female has led Russian scientists to predict he has 16 million male descendants living today: the most loathsome of lotharios.

Exploits: all of Mongolia

Giacomo Casanova (1725 – 1798)


Venetian adventurer and author, Giacomo Casanova, has long sparred with Don Juan (in Italian, Don Giovanni) for the name most synonymous with the art of seduction. Perhaps he was inspired by the exploits of his fictional progenitor, for he was apparently present at the first performance of Mozart’s opera Don Giovanni in 1787. Regardless, Casanova proved many times over to be an adept, unscrupulous lover, who believed he was born for the opposite sex. His first sexual liaison was with two sisters, Nanetta and Maria Savorgnan, a precocious introduction to carnal pleasures and a taste of things to come.

Exploits: 120 with women and girls mentioned in his memoirs, as well as many veiled references to male lovers.

Pablo Picasso (1881 – 1973)


Fernande, Eva, Olga, Marie-Therese, Dora, Francoise, Jacqueline: these are the names of the important woman in the life of seminal Spanish artist, Pablo Picasso. Though each of these women played a crucial role in the painter’s life and art, each was replaced by another, with all but one suffering some sort of mental breakdown in his wake. Post-Picasso, Fernande Olivier lived in sorrow until her death; Olga Koklova became his fitful stalker; Marie-Therese Walter hanged herself; Dora Maar became a recluse; Jacqueline Roque shot herself when he died; only Francoise Gilot, who began her affair with the sixty-something Picasso when she was 23, avoided an unhappy fate.

Exploits: quite a lot; often fatal

John F. Kennedy (1917 -1963)


A beautiful wife (Jackie Onassis) and a sex-bomb mistress (Marilyn Monroe) were not woman enough for former US president, John F. Kennedy. The glamorous head of state once confided that if he went too long without a woman he’d suffer a clamorous headache; a fate he took pains to avoid. Linked to a string of high-profile women, including actresses Jayne Mansfield, Angie Dickinson, Kim Novak, Janet Leigh and Rhonda Fleming, he is suspected to have had several more encounters with women relatively unknown. Thanks to his dashing good looks and sexual precocity, coquettish young women would apparently more or less queue up at the door to the White House asking for Mr President.

Exploits: more than Clinton

Ian Fleming (1908 – 1964)


It should come as no surprise that the creator of James Bond, the fictional spy who spends as much of his time gathering beautiful women as he does intelligence for the secret service, was himself a jet-setting womanizer with a predatory disposition. Evidently irresistible to women, Fleming could seduce them in four languages, and went about doing so with Bond’s aplomb. His friend Mary Pakenham once said: ‘No one I have ever known had sex so much on the brain as Ian.’ Yet, though he loved women, he evidently didn’t like them much, once telling a friend women were like pets or dogs; men were the only real human beings, the only ones he could be friends with.

Exploits: various, sometimes involving whips.

Hugh Hefner (1925 – present)


For Hugh Hefner, womanizing is not so much a hobby as a career and a way of life. The Octogenarian founder of soft-porn magazine, Playboy, surrounds himself with as many scantily clad ‘Playmates’ as he can, promoting his lifestyle to his magazine readers, while blithely eschewing a more politically correct attitude towards women. Some say Hefner developed his errant ways after discovering his first wife had had an affair while he was away in the Army in the 1950s. One profile of the bon vivant claims his wife had allowed him to sleep with other women as recompense for her infidelity, in the hope it would save their marriage. Mistake: they divorced in 1959 – though her loss was the porn industry’s gain.

Exploits: up to seven at a time, including Donna, Marilyn, Lillian, Shannon, Brande, Barbi, Karen, Sondra, Carrie, Izabella, Tina, Holly, Bridget and Kendra, to name a few.

Wilt Chamberlain (1936 -1999)


Wilt Chamberlain, the late American professional NBA basketball player, is as famous for playing the ladies game as he is for the ball game. His claim to sexual fame was that he had bedded some 20,000 women during his lifetime, which, if true, would mean he had slam dunked an average of 1.14 women a day. Though the claim brought him derision, being oh-so-unlikely, he was nevertheless a bona fide tomcat and interminable pick-up artist. Like Hefner, his extreme sex drive is thought by some to be down to overcompensating for female rejection during his teenage years.

Exploits: 20,000 women if you can believe it.

Jack Nicholson (1937 – present)


Jack Nicholson, he of the pointy eyebrows and the rictus grin, is a lady-magnet whose magnetism no lady can resist. The Oscar winning actor is famous for his lascivious pursuit of leading ladies, allegedly bedding 2,000 women and spawning six children to five mothers. His longest relationship was with Angelica Huston, which lasted for 16 years, ending when the media reported that Rebecca Broussard had become pregnant with his child. His louche behavior has continued into his dotage – though at 71 he admitted ‘it’s not so nice when you are 71 and looking for some action’. Still, the old roué’s reputation is assured, and he once featured in Maxim magazine’s Top Ten Living Legends of Sex list.

Exploits: actresses and models mainly, including Michelle Phillips, Bebe Buell, Lara Flynn Boyle, Angelica Huston, Lorraine Nicholson, Susan Anspach, Amanda de Cadenet and Amber Smith.

Warren Beatty (1937 – present)


Warren Beatty beats even Jack for the mantel of Hollywood’s most notorious womanizer. Now in his seventies, and happily married to actress, Annette Bening, in his relative youth the Oscar winning actor and director was unrivalled in his lady-winning ways. At the outset of his career he allegedly dated Natalie Wood while making Splendor in the Grass, abandoning her in a restaurant after making a successful pass at a waitress. He went on to date, and bed, and kiss and grope so many women that Woody Allen once joked that if he believed in reincarnation he would come back as Beatty’s fingertips. In 2009 a biographer claimed that Beatty had slept with around 12,775 women, though Beatty disputes the figure. It is widely rumored Beatty is the subject of Carly Simon’s hit song You’re So Vain, though she has never confirmed this.

Exploits: too many mention, but, for starters: Julie Christie, Jacqueline Kennedy, Joni Mitchell, Bianca Jagger, Diana Ross, Diane Keaton, Maria Callas, Faye Dunaway, Princess Margaret, Linda McCartney, Vivien Leigh, Vanessa Redgrave, Brigitte Bardot and Cher.