Most men have a weakness, whether it’s gambling, booze, lying, infidelity, or what have you. We’ve found that the more serious the flaw, the more it’s grounded in compulsion. Throughout history, men of the highest stature, intellect, and position have found themselves unable to resist the allure of women of the night. Whether it be the result of the time, or carnal needs of the man, these figures could not live without paid female companionship…
10. Marquis de Sade (1740-1814)
Although Marquis de Sade was a French aristocrat, author, and revolutionary, he’ll always be best known for his sexual deviance; the term sadism being a derivation of his last name. To understand Sade’s sexual compulsion and obsession with prostitutes, it’s more important to understand the aristocrat’s childhood. Abandoned by his father and mother, Sade was raised by his servants and was eventually sent off to a boarding school. Sade was spoiled by his servants, who accepted his every request, which made his time at boarding school difficult. He was a victim of cruel corporal punishment including flagellation. Soon after leaving school, his obsession with prostitutes would begin.
The first recorded instance of Sade’s interactions with a whore occurred when he was just 23. Sade hired a woman named Jeanne Testard, who he made observe him as he masturbated on an ivory statue of Jesus Christ. Another notable encounter took place five years later, when he was arrested for tying down a prostitute and whipping and stabbing her buttocks. Sade’s cruelty had no ends. He’d later face charges for feeding several prostitutes an aphrodisiac (Spanish Fly), then sodomizing and whipping them.
Sade would become wanted by French authorities and eventually was arrested for his crimes. His arrest was not simply for his crimes against women but blasphemy. While in prison, Sade wrote several of his most prominent erotic novels and short stories.
9. Henri De Toulouse-Lautrec (1864-1901)
Another Frenchman on our list is painter Henri de Toulouse-Lautrec. Born in 1864 to an aristocratic family that had a history of inbreeding, Lautrec suffered from significant physical defects. After breaking both femurs in his teens, they never healed properly due to a genetic disorder; as a result, his legs failed to grow, leaving him with an adult-sized torso and a child’s legs. Unable to participate in sports and other activities, Lautrec immersed himself in art. However, art was not the only thing he found himself obsessed with. Accounts shows that Lautrec lived in several brothels over the course of his life, believing himself to be “an aristocrat cut off from his kind.”
The women of the night also began to be the subjects of his artwork. Lautrec rewarded them with presents and nights out to restaurants, theaters, and circuses. His own physical limitations clearly gave him an affinity for these women, both being ostracized from mainstream society. Eventually, Lautrec would fall victim to his lifestyle. He contracted syphilis from a prostitute and died at the young age of 36.
8. Rasputin (1869-1916)
It’s not hard to believe the Tsar was overthrown during Grigori Rasputin’s time as a trusted adviser and faith healer. Born to a peasant family, Rasputin made a meteoric rise through the rigid feudal system of Russia. In 1897, Rasputin went on a pilgrimage to a monastery and returned a transformed figure, who was able to impress local church and societal leaders. Eventually, his influence swelled to the point where he was introduced to the Tsar of Russia, Nicholas II. His influence over the Tsar and his family began to irk conservative members of the government who soon plotted his downfall. Critics of Rasputin were not only jealous of his influence but his odd and compulsive behavior.
Rasputin’s behavior became monitored and it became known that he would “hire prostitutes several times in the course of a single day.” His obsession with the female body went to such lengths that in some instances he would not even sleep with the hired women. Agents hired to follow Rasputin observed that he bought a prostitute two bottles of beer, but did not have any of it himself. He then asked her to undress, studied her body, and left. Time and time again, he’d be observed entering a hotel room, bathhouse, or some other secluded place with a prostitute, only to leave 20 minutes later. With the Tsarist government on the brink of collapse, Rasputin was seen as a corrupting influence and was assassinated by right-wing figures close to the Tsar.
7. James Boswell (1740-1795)
James Boswell is best known as the author of the biography of Samuel Johnson. The work has since been lauded as the best biographical work ever written in the English language. Boswell was quite good at one other endeavor: the pursuit of harlots. Over the course of his life, the biographer was known to have relations with at least 60 different women of the night. Boswell continued these liaisons despite having contracted gonorrhea on at least 19 different occasions. In his diary, Boswell described his futile attempts at refraining from engaging in such lifestyle only to find himself at a whore’s door soonafter. Boswell believed his salvation came in the invention of a primitive condom, calling it his “armor.” He carried one with him at all times, not knowing when the moment would strike that would see him running to the brothel doors. Boswell’s diary gives amazing insights into his various and frequent encounters: “I should have mentioned last night that I met with a monstrous big Whore in the Strand…”
Another amazing story details a sexual encounter that took place on the Westminster bridge: “I picked up a strong jolly young damsel, and taking her under the Arm I conducted her to Westminster-Bridge, and then in armour compleat did I engage her upon this noble Edifice. The whim of doing it there with the Thames rolling below us amused me much.” It should not be surprising that Boswell died as a result of a venereal disease he contracted.
6. Vaslav Nijinsky (1889-1950)
The ballet is known for its sophistication, but Vaslav Nijinsky seemed determined to break that convention. The famous Russian ballet dancer and choreographer was obsessed with prostitutes, admitting that he “made love to several tarts a day” while touring in Paris. During a trip to Zurich, Nijinsky admitted in his notes that he would not have much time for entries, as he would be too busy at brothels.
Nijinsky would go on to say he had an almost compulsive need “to have an intuitive understanding of tarts.” Lamenting his obsession, Nijinsky admits his frequent visits to brothels was “terrible,” yet he confesses to looking for whores each day. After one particular unsuccessful day, Nijinsky complained about not being able to hire a prostitute because he wasn’t familiar with the area. Historians have come to believe that Nijinsky’s obsession with women of the night was due to his androgynous roles in many ballet productions. Maybe his success in those roles was due to his familiarity with those “tarts” he was so fond of.
5. Gary Ridgway (1949-present)
While most men on our list have had perverse, morbid, and even ill-natured obsessions with prostitutes, Gary Ridgway’s obsession made him the most prolific serial killer in American history. The Green River Killer was convicted of 49 murders but would eventually confess to taking the lives of 71 people. Ridgway had a troubled childhood, witnessing violent encounters between his parents. His father would openly complain about the existence of sex workers in the neighborhood, which may have stuck with Ridgway as he grew older. Ridgway admitted that he began soliciting prostitutes in his early 20s, and that after his second divorce his encounters only increased. Soon after, he said he developed “a growing hatred toward the prostitutes he visited.”
Ridgway tricked the prostitute or runaway into trusting him by showing a picture of his son, then after raping them, he’d strangle the unsuspecting woman. He did this for quite some time until he “stopped being able to have sex with a living person so he would rape the still warm corpses.” The demented man would bury his victims and then unearth them later to have sex with the corpses again. DNA evidence would link Ridgway to the bodies of four women and after questioning he’d finally admit to the terrible deed and reveal the location of other bodies in exchange for a life sentence.
4. Charlie Sheen (1965-present)
It’s hard not to include Charlie Sheen on any list including prostitutes. The star of iconic films like Platoon and Wall Street, Sheen seems to be closer to one of his last roles, that of the lead character in the sitcom Two and a Half Men. Like his character in the show, Sheen frequently pays for prostitutes, to the tune of $1.6 million in just one year. Co-star Jon Cryer even got into the act with the help of Sheen. Mirroring the television show, Cryer admits that after his divorce Sheen helped him hire a prostitute.
However, Sheen’s actions have not been harmless. Sheen has admitted to being HIV positive, and several of his partners have expressed outrage that the actor did not divulge his condition.
3. Diego Rivera (1886 -1957)
The Mexican painter who helped establish the mural movement in his home country is probably better known for his relationship with Frida Kahlo. Diego Rivera’s work should not be scoffed at, of course, with several of his paintings held at the Museum of Modern Art in New York. His work, particularly the murals, told stories that were socially conscious. Rivera was not afraid to use art to convey political opinions. In the painting Dreams of a Sunday in the Alameda he depicted Mexican politician Ignacio Ramírez holding a sign which read, “God does not exist.” The work was met with outrage, but Rivera refused to remove the inscription. His rebelliousness would eventually shift into a sort of madness.
Later in life, Rivera bragged about having prostitute mistresses at the age of six years old, admitting to frequenting sex workers as a youth. His behavior would take an even darker turn as Rivera and his fellow artists would experiment in cannibalism. We know what you’re thinking: how can you “experiment” in eating human flesh? Let’s just say Rivera, on more than one occasion, bought undiseased corpses from the mortuary. Rivera was said to have especially enjoyed the breasts and thighs of women for his cannibalistic feasts.
2. Thomas Wolfe (1900 -1938)
Although Thomas Wolfe’s novels and short stories have not really passed the test of time, he was seen as one of the best American writers in the early 20th century, with William Faulkner stating he was the greatest talent of their generation. Wolfe died from pneumonia at the age of 38, a sudden end to a life filled with much promise and strife.
Those who knew him described Wolfe as a tortured man, an alcoholic with many vices including his obsession with prostitutes. Wolfe would admonish his lover and inspiration for being unfaithful while he would abandon her at night for the companionship of a lady of the street.
1. King Charles II (1630 -1685)
The death of Oliver Cromwell led to a political crisis in England and ultimately restored Charles II as monarch. In English history, King Charles II is viewed as one of the most beloved monarchs, partly because of the return to normalcy, but also because of the liveliness and hedonism of his courts and proceedings. It was well known that Charles II was a philander, and he was said to have fathered 13 children from mistresses and whores that he frequented. Although Charles II went from one woman to the next, we’d like to focus on one particular “mistress” he took a liking to. Nell Gwyn was born to a brothel owner, and was made to work “selling snacks” at a young age. When she became a young adult, Gwyn met Charles at a play, where he invited her to back to his castle. Charles was struck by her wit and continued to see her; little did Charles know, Gwyn was well aware of his other mistresses and went on to poison her rivals with laxatives as to continue to see the King. Eventually Gwyn became well known to the public and when insulted admitted, “I am a whore. Find something else to fight about.”
It’s hard not to see Nell Gwyn as a woman born in the wrong time; her wit and humor would have made her a star on comedy shows like Saturday Night Live. Another of Gwyn’s quips was prompted when a crowd of people surrounded her carriage. Believing they had come across another of King Charles II’s mistresses, the Duchess of Portsmouth, the crowd yelled at Gwyn, calling her a Catholic whore. Composed and with even a slight smile on her face, Gwyn stuck her head out of the carriage and said, “Good people, you are mistaken. I am the Protestant whore.” One heck of a line.