Who needs modern medicine and basic hygiene? These historical hotties make us want to jump in a time machine. From Lord Byron and Casanova to Anne Lister and Cleopatra, these old-school heartthrobs prove that well-behaved people rarely make history. These flirts would do anything—and we mean anything—to get some. Get ready to take notes: Our thirst is eternal for these old-school playboys and maneaters.
Historical Heartthrobs Facts
1. Don't Hate The Player
Giacomo Casanova was an 18th-century Italian adventurer best remembered for his scandalous catalogue of exploits. His name has been immortalized as the byword for “lady-killer,” and one doesn’t achieve such infamy by being a serial monogamist. Casanova’s treatment of women certainly warrants criticism, but his scandals barely hold a candle to the long list of scams he waged against Europe's ruling elite.
2. Too Hot to Pray
Casanova was at first dead-set on a career in the church (ha!). Unfortunately, his lady-killer good looks mixed badly with his gambling addiction and put a stop to that pious future. As a young abbé, he got into so much gambling debt that he wound up in debtors’ prison.
3. Beauty, Brains, and Non-Stop Pleasure
A woman named “Henriette” was the “love” of Casanova’s life. Not much is known about her beyond Casanova’s written valuation of her as both incredibly beautiful, incredibly smart, and able to please him in every way 24/7. But at the end of their three-month affair, Henriette slipped five-hundred louis into his pocket as her meager valuation of their relationship. He was heartbroken; while Casanova would write to her for years, the couple would never meet again.
4. Worshipping With All His Parts
On the run in Switzerland for unpaid debts in 1760, Casanova considered giving up his sex-addled chaos trip of a life and become a monk. A nice visit to an Einsiedeln monastery caused him to deeply reevaluate his choices. He walked back to his hotel to seriously think this career change over…only to come across a new “object of desire,” and then immediately go on a year-long sex tour from Marseille to Genoa, Florence, Rome, Naples, Modena, and Turin. As one does.
5. Somebody Has Watched Tom Hanks’s Big Too Many times
In the early 1760s, Casanova found himself back in Paris to commit his most famous con: trick the Marquise d'Urfé into thinking he could magically transform her into a young man. Shockingly (I know!), this plan only lasted for a little bit until the aristocrat caught on. But hey, even so the scam wasn’t a total bust. Casanova sold the loot he had stolen from her to fund his next venture: promoting the state lottery to King George III of England.
6. The English Dub Is Always Worse
Casanova, however, did not speak English, which presented a problem when attempting to charm women on the British Isles. To overcome the language barrier and still get it on in the bedroom, he put out an ad in the paper seeking to "rent" his apartment to the “right” lady. His favorite candidate was a “Mistress Pauline.” As a reward for his lusty schemes, Casanova left England with a venereal disease and yet another empty bank account.
7. Two out of Three Pleased Ain’t Bad
Casanova lost his virginity at age 17 to two sisters, Nanetta and Marta Savorgnan. In fact, everyone in this scandalous triad was a virgin. He had at least one bad review of this experience: Marta would end up joining a convent and praying for the redemption of Casanova’s soul. Good luck with that, girl.
8. More Than Meets the Codpiece
Casanova once fell in lust for a young man who turned out to be a woman in disguise. The supposed castrato—which is basically a young male opera singer who castrates himself to remain high-voiced—went by the name of “Bellino.” In truth, Bellino was a young actress who cross-dressed to advance her career. Although Casanova calls her Teresa Lanti in his memoirs, her exact identity is still a mystery.
9. Where’s His Netflix Show?
In between his many bedroom romps, Casanova also found time to become a professional gambler, work as a spy, and get a law degree at just 17 years old. But he wasn't just an over-achieving yuppie. This bad boy also went to jail for being "an affront to religion and decency" then escaped from jail (with a priest!) and promptly dug up a corpse to prank a frenemy. Sometimes Casanova's womanizing makes me mad, but right now all I feel is respect.
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10. The More the Messier
In his memoirs, Casanova claims he had a kind of ménage à trois with two nuns. After impregnating Caterina Capretta, he continued to hook up with her even after she was sent to a nunnery. During this time, he also began an affair with another nun at the convent, Marina Morosini. Casanova and Morosini even put on a “show” for the latter’s other male lover, who was watching from a secret room. And for the record, Morosini and Capretta—yes, that first nun-lover of Casanova—had already engaged in their own same-sex relationship from within the convent. Does that make this a love square?
11. Can I Ask WedMD About This?
In 1759, Casanova tried to help his old friend Guistiniana Wynne get an abortion (not his baby for once) only to end up sleeping with her himself. He procured an ointment that would supposedly act as an abortifacient, but it had to be applied with his “private” parts, or so he claimed. At that stage, one starts to question how earnestly Casanova was trying to “help.” To no one’s shock, this did not work, and Wynne fled to give birth in a convent.
12. Too Close for Conscience…
Unsurprisingly, Casanova fathered too many illegitimate children to keep count. This got dangerous in 1761, when (so he claims) he almost took a woman named Leonilda as his mistress. Just before he brought her into his bedroom, he found out that she was actually his daughter, and pulled back from the affair. But the worst wasn't over.
13. …At Least For a While
But Casanova’s reunion with Leonilda had a horrific ending. Many years after he withdrew from their tryst, her mother (and his old flame) Lucrezia Castelli invited him to stay with her and Leonilda, who was now married. While he visited, mommy dearest revealed that Leonilda desperately wanted a child, but her husband was unable to giver her one.
Disturbingly, she then begged Casanova to impregnate Leonilda. Ew. Even more unsettling, he actually did it. That's right, if we are to believe his writings, Casanova fathered his own grandson.
14. Queen of the Nile
Even today, over 2,000 years after her death, Cleopatra remains one of history’s most intriguing and memorable women. And for good reason: her reign is rich in story and scandal. The Egyptian Queen commanded her own army, enamored not one but two Roman rulers, and inspired countless works of art, literature, and film. Her prowess as a ruler made her legendary, and the stories of her romances with Julius Caesar and Marc Antony made her unforgettable.
15. The Beauty Myth
The name “Cleopatra” has become synonymous with exotic beauty and allure, but the real Cleopatra’s beauty was further down the list of her charms. Coins showing her face display a somewhat homely woman with a hooked nose. So how did Cleopatra go down in history as the most gorgeous woman of all time? Her sultry personality: According to Plutarch, her wit, charm, and “sweetness in the tones of her voice” made her irresistible.
16. Watch the Queen Conquer
When Cleopatra’s father, Pharaoh Ptolemy XII, died, his will made 18-year-old Cleopatra and her 10-year-old brother joint rulers. Because of a creepy custom, she was forced to marry her brother but that union didn't last long. Within months of taking the throne, Cleopatra made it clear she had no interest in sharing her power. She erased her brother’s name from official documents and only her face appeared on coins.
Only a year after becoming the Queen of the Nile, the Romans helped Cleopatra's husband-brother usurp his sister-wife's throne. After losing a key battle, Cleopatra fled. Just when it looked like it was all over, our girl Cleo staged one of history's greatest comebacks. Cleopatra promptly hooked up with Caesar, the ruler of Rome, moved into her boyfriend's city, and had his illegitimate baby. The devil works hard but Cleopatra works harder.
18. That's One Way to Make an Entrance
Cleopatra, clever and charming, certainly knew how to make an entrance. In order to meet Caesar face to face, in hopes of enticing him over to her side, she had herself smuggled through enemy lines while rolled up in a carpet, which was brought to Caesar’s private quarters. When unrolled, a nude Cleopatra emerged and immediately charmed Caesar.
19. Et Tu, Sis?
Cleopatra’s sexy times in Rome came to an end when Julius Caesar was stabbed to death in 44 BC. She fled Rome and, after her brother-husband Ptolemy XIII drowned in battle, returned to Egypt. Once there, Cleopatra promptly married another of her brothers. Instead of waiting for this sibling to get any ideas about overthrowing his big sis, Cleo sped things along and had him murdered. With another pesky relative out of the way, Mama Cleo and her son Caesarion took the throne.
20. A Grand Entrance
Cleopatra's meeting Marc Antony was truly dramatic. When she was summoned to meet the three men who now ruled Rome, she sailed down the Nile on a golden barge adorned with purple sails and silver oars. Cleopatra, dressed as the goddess Aphrodite, arrived to meet Marc Antony. Unsurprisingly, he was immediately whipped.
21. Partners in Love
Cleopatra and Marc Antony quickly became inseparable. The lovers hunted together, played pranks, founded a drinking club, and in a delightfully thirsty gesture, Cleopatra would watch her man do his work outs. They stood together as partners against Egypt’s enemies, and were married in an Egyptian ceremony—despite the fact that Antony already had a wife in Rome.
22. Got a PhD in Flirting
In one of Antony and Cleopatra’s elaborate contests, she bet him that she could throw the most expensive dinner in history. After an unremarkable first course, Antony mocked her attempt. However, when served his second course, he was shocked to discover that his dish contained only strong vinegar. Cleopatra plucked a pearl from her earrings and dropped it into the vinegar, wherein it began to dissolve, and promptly gulped it down. Historians estimate that it was worth millions.
23. The Original Yoko Ono
Cleopatra and Marc Antony didn't get to enjoy each other's company for long. The other Roman rulers called Antony a traitor and made fun of him for not wearing the pants in his relationship. After smearing Cleopatra as a scheming temptress (to be honest, they weren't wrong), Rome declared war on Egypt in 33 BC.
24. By Her Own Hand
Even when Cleopatra died, she managed to be cool. Instead of waiting for her enemies, Cleopatra induced an Egyptian cobra to bite her. Upon hearing of his lady's death, Marc Antony took his own life by stabbing himself in the stomach. But some sources suggest an even more tragic end: Antony stabbed himself, only to find out that Cleopatra was still alive. After being brought to his lover, he died in her arms, leading Cleo to kick the bucket. Violence is so romantic.
25. Mad, Bad, And Dangerous To Know
Hailed as one of the greatest poets in the history of the English language, Lord Byron's writing continues to be admired and studied to this day. What has also endured, however, is Byron's dark legacy as a person, with a history of heartbreak, seduction, and taboo relationships to his name. He was called "mad, bad, and dangerous to know" for a reason, people.
26. Playboy Poet
Byron allegedly wrote his first poem in 1800. It was a love poem written in honor of his, er, cousin, Margaret Parker. In fact, Parker wasn’t the only one of Byron’s cousins to catch his eye: he also felt a romantic attachment to his relative Mary Duff. Not cool, Byron.
27. He Went Both Ways
But female relatives were far from Byron's only love interests. While studying at Trinity College, Cambridge, the poet developed a very close relationship with a younger student named John Edleston, referred to as Thyrza in Byron's poetry. One excerpt reads, "The whisper'd thought of hearts allied...The kiss so guiltless and refin'd." Get it, Byron.
28. Mediterranean Holiday
Some scholars believe that when Byron went on his Grand Tour (a rite of passage for wealthy young men), he chose to travel specifically to the Mediterranean because that region was much more accepting of queer relationships. Indeed, while in Greece and Turkey, Byron enjoyed relationships with noted hotties Eusthathius Georgious and Nicolo Giraud.
29. Love 'Em and Leave 'Em
When Byron returned to England in 1811, he promptly engaged in some characteristically volatile romances. It was a well-publicized scandal when Byron was discovered having an affair with Caroline Lamb, who was a married woman at the time. The poet soon moved on, but Lamb never got over their fling. She would stalk him, sometimes even in disguise, in the hopes of winning him back. But that wasn't even the worst of it.
Her deteriorating emotional state caused her to lose so much weight during this time that Byron joked to his friend that he was being “haunted by a skeleton.” When she left a message saying, “Remember me!” on his desk, Byron mocked the message with a poem that he titled “Remember Thee! Remember Thee!”
30. Lost the Breakup by a Hair
Even after their horrible breakup, Lamb wanted a particular portrait of Byron to remember him by. After forging a letter (thirst is the mother of creativity), she managed to get her hands on the pic, only for Byron to realize what had happened and demand that she give it back. To Byron's surprise, Lamb agreed to return it—but she had one creepy condition. She wanted a lock of his hair in exchange for the painting. This is when Byron took “sick burn” to the next level.
Reader, he sent over a lock of his new girlfriend’s hair.
31. Twice Beloved
One of the wildest rumors about Byron’s love life was that he had an incestuous affair with his half-sister, Augusta Leigh. Having grown apart in their youth, Byron and Leigh later did develop a very "close" bond as adults. Historians are deeply divided to this day just how close these two actually were, but a few experts do suspect that Leigh’s daughter Medora was the fruit of a love affair with Byron.
32. Til Debts Do Us Part
Whether or not these rumors are true, they spurred Byron into a quick marriage with Annabella Millbanke, the mother of his legitimate daughter Ada. Unsurprisingly, it was not a happy union. Pretty soon, Millbanke became certain that Byron was insane and still obsessed with his half-sister Augusta. She separated from him and he, still dogged by rumors and his many debts, fled to mainland Europe. He would never return while he was alive.
33. It’s All Greek to Me
The last years of Byron’s life were spent in Greece, trying to raise money for the Greeks as they struggled to fight for independence from the Ottoman Empire. Another of his hobbies while in Greece? For some scholars and biographers, Byron's great passion was lusting after young men. In a poem about a Greek boy named Lukas Chalandritsanos (who was either ignorant of Byron's feelings or, in a new experience for Byron, playing hard to get), Byron moans that he "lov'st me not." We've all been there, Byron.
34. The Playboy Poet Perishes
Byron suddenly took ill in February 1824. Though for a time it seemed like he might recover, in April he contracted a ruthless fever and was dead within days. Historians still puzzle over his death, but they've suggested a disturbing possibility: the treatment for Byron's illness involved blood-letting, which was likely carried out with non-sterilized instruments. With such unsanitary conditions, the great poet may have died of sepsis. He was 36 years old.
35. Gentleman Jack Comes to Call
For those who haven't heard of Lister or seen the recent HBO/BBC show based on her diaries, this fascinating figure has been called “the first modern lesbian.” She never apologized for her romantic pursuit of women, traditionally masculine outfits, or her aggressive business style, and clearly the ladies liked it. Lister has gone down in history as one of history's great heartbreakers.
36. Young Love
When she was 13, Lister was sent to the Manor House School at York. At this tender young age, Lister fell in passionate love with her school roommate, Eliza Raine. The teenage girls were utterly devoted to each other, and even planned to live together once they grew up. Sadly, they were forced apart: officials discovered the relationship and expelled Lister from the school.
37. Cheater, Cheater
Lister was allowed to re-enter Manor House School after two years, but it was too late: her young love Eliza had already left the establishment. Even so, the girls had sworn to love each other forever, and Eliza was sure they would end up together soon enough. Instead, Lister dealt Eliza an absolutely cold-hearted betrayal.
In Eliza’s absence, Lister struck up a series of relationships with other girls in the school. When Eliza found out, she was so devastated that she had to be committed to an asylum.
38. Mutual Acquaintances
As if she hadn't had enough sorrow already, Eliza Raine's heartbroken asylum visit contained a horribly cruel irony. Her family sent her to Clifton Asylum, an establishment run by a man named Dr. Belcombe. This Dr. Belcombe just so happened to be the father of Lister’s latest romantic pursuit, a beautiful girl named Mariana.
During this time in her life, Lister was becoming confident, handsome, and utterly irresistible to many bright young women. In fact, Lister had been introduced to the lovely Mariana Belcombe by another of her conquests, a beauty named Isabella Norcliffe. Of course Lister later rejected Isabella for Mariana—again with disastrous results.
Forever stung by Anne's cruel rejection, Isabella took to drinking and remained single the rest of her life.
40. Curious Renovations
Upon inheriting Shidben Hall, Lister immediately began improving the grounds. She added vast gardens, a lake, and even hired an architect to built a gothic tower on the main building of the grounds, which she then used as a library. But Lister's renovations did more than beautify; they also helped her keep company with local ladies.
Lister would test the waters with potential lovers in her library by mentioning writers whose works had overt homosexual themes, and then gauging her listener’s response. More to the point: she also constructed underground tunnels so she could avoid servants—and sneak in lovers.
41. The Lady in Black
Lister was a conspicuous figure around Halifax. She usually wore heavy leather boots, constricting bodices, and carefully tailored long coats. As a rule, she dressed in black, which she felt gave her a masculine, angular look. While the townspeople mocked Lister with the nickname Gentleman Jack, clearly, Lister's suave aesthetic appealed to many of the women nearby.
42. For Love or Money
In 1832, Lister met Ann Walker, a pretty and wealthy heiress. Walker was 12 years Lister’s junior and could be a very impressionable, passive girl. At the time, Lister was in dire financial straits but had always been unwilling to marry a man for stability— so she saw long-term relationship potential in Walker, who could support her without trying to dominate her strong will.
43. The Waiting Game
Lister invited Walker to live with her and join in a relationship almost immediately. Walker was reluctant, however. Her parents had recently passed away, as well as a fiancé, and she was worried about how the public would perceive the arrangement. She asked Lister to give her six months to think it over, during which time Lister went traveling in Denmark.
When Lister returned, Walker was waiting for her at Shibden Hall, with news that she had rejected a marriage proposal from a local gentleman. From that point until Lister’s death, Lister and Walker were inseparable. It may not have been a passionate love match from the start, but it was a love story in the end.
44. Going to the Chapel
On Easter Sunday, 1834, Anne Lister and Ann Walker went to Holy Trinity Church in York. There they exchanged rings and took communion. The event is now considered the first lesbian wedding in England. It would be 180 years before same-sex marriage would be made legal in the UK, and the Church of England still does not recognize such unions.
45. Third Wheel
Shockingly, though, this was far from Lister's first marriage. Years before her vows with Walker, Lister had previously shared a ceremony with Mariana Belcombe, going so far as to exchange rings as well. It did not end happily: Mariana eventually married a man, voiding the emotional union and crushing Anne—but that was far from the worst part.
Unable to let Mariana go, a heartbroken Lister even accompanied her newly-wedded friend on her honeymoon. Sounds awkward, to say the least.
46. Breaking Up Is Hard to Do
In spite of the marriage—and Lister’s brief affair with Mariana’s older sister—Lister and Mariana couldn't stay away from each other. The next year, they fell back into bed with one another, despite the looming presence of Mariana's new husband. Again, heartbreak was around the corner: it finally ended 1823, when Mariana decided she could no longer risk the gossip that followed them. While their love may have ended, Lister's reputation as the world's top lesbian never faltered. We still love you even if Mariana doesn't.
47. King Henry VIII: The Worst Monarch in History
England has had some randy monarchs in its time, but King Henry VIII just might be the most groin-motivated ruler in the country's history. He was married six different times, started his own religion to get a divorce from his first wife, and through it all, still managed to have affairs. Love him or hate him, no one can deny that Henry VIII took "ladykiller" to the next level.
48. Small World
It may seem like Henry VIII searched far and wide for a suitable wife, seeing as he infamously married six different women, but he didn’t look as far as you might think: Henry and each of his wives were all descended from King Edward "Longshanks" I, meaning that they were all cousins to one degree or another. He definitely had a type.
Henry VIII was consumed by his desire to father a son—something that proved famously difficult for him. Catherine of Aragon bore Henry six children in total, including two sons, but all but the future Queen Mary died in infancy. Henry VIII was desperate for a male heir to secure the royal lineage, and he was none too happy. Catherine's early "failure" left Henry in a precarious position, and he started to look for his next wife...
50. Keeping it in the Family
King Henry VIII’s interest in his future Queen Anne Boleyn was controversial, and not just because he was already married. Henry was actually already having an affair with Anne’s older sister, Mary Boleyn—but it gets even worse. There were also rumors that Henry had bedded Anne and Mary's mother, Elizabeth. When accused of this one, Henry protested, "Never with the mother."
51. That's "Queen Anne" to You
It took a while, but in 1533, it finally happened: after many machinations and splitting from the Catholic Church, Anne Boleyn became Queen Consort of England, ruling beside Henry like she always wanted. Of course, the power couple had already married each other in two private, very confidential ceremonies, and Anne was already pregnant.
52. Citizen Jane
King Henry VIII always had a wandering eye, and when his marriage with Anne started fraying, he turned his attentions to the pretty, sweet, and submissive Jane Seymour, who would eventually become his third wife. Just like with Anne's sister Mary, Henry liked keeping it in the family: Seymour was also Boleyn's second cousin. Confirming his playboy ways, somehow Henry considered her his first "true wife."
53. End of the Road
In May 1536, Anne's luck finally ran out. King Henry VIII claimed he had been seduced and enchanted into a marriage with Anne, and ordered her locked up in the infamous Tower of London to await her fate. Boleyn was accused of adultery with men including her own brother George, and charged with plotting to murder the king so she could marry one of her lovers. Modern historians agree that the charges were false. Henry had her killed just because she didn't give him any male children.
54. Which One?
King Henry VIII was a pretty heartless guy, and as much as people have romanticized his great love for Jane, having a son and heir was always his number one priority. Jane’s labor was difficult, and when asked by an attendant whether he wanted to save the mother or child if it came down to it, his reply was absolutely chilling.
Henry supposedly replied, “If you cannot save both, at least let the child live," followed by the characteristic statement "for other wives are easily found.” Priorities, right?
55. Renaissance Tinder
After Seymour's death from complications after giving birth to Edward VI, Henry VIII began the search for his next wife. In order to choose, Henry was sent paintings of possible partners. He chose Anne of Cleves over her sister Amalia, but was unhappy with his choice when he finally saw her in person. Apparently, she wasn't quite the looker he had hoped for.
He called her a “fat, Flanders mare,” and had the marriage annulled after just six months. At least she kept her head!
56. Off With Her Head!
16 days after annulling his marriage to Anne of Cleves, Henry VIII (now 49) married the 19-year-old Catherine Howard, who had been Anne of Cleves' lady-in-waiting. Less than a year into their marriage, rumors of her infidelity began, and after gathering evidence of her promiscuity, Henry had her executed in 1542.
57. Outlived, Outlasted
Henry VIII’s sixth and final wife Catherine Parr managed to not only hang onto her head, she also outlived her husband. Catherine Parr also played a key role in restoring Henry's daughters Princesses Mary and Elizabeth to the line of succession—after Henry had rendered them illegitimate by annulling his marriages to their mothers.
58. Any Last Words?
Despite being known for his vigor and athleticism as a young man, Henry’s massive weight gain and the subsequent decline of his health finally caught up to him, and he died in 1547 at the age of 55. His final words are not known for sure, but it has long been rumored that he cryptically cried, “Monks! Monks! Monks!” before his final breath left him. Maybe he finally felt bad for being such a horndog? We can only hope.
59. Watch Out Boys, She'll Chew You Up
Duchess. Bigamist. Hustler. Criminal. Say what you want about her, Lady Elizabeth Chudleigh definitely made an impression. This scandalous courtier has gone down in history for the 18th century’s most shocking trial—but few people know about her other jaw-dropping claims to fame. Raise your champagne glass and give a toast to Lady Chudleigh, the maneater of the 1770s.
60. Friends in High Places
When Elizabeth’s father died, a fancy friend named William Pulteney got her a cushy position as the Princess of Wales’ Maid of Honor. But some sources claim that Pulteney didn't help out of the goodness of his heart. Even though he was married and firmly in his 50s while Elizabeth was barely 21, they might have been a romantic item. Pulteney was entranced by Elizabeth’s beauty and flirtatious quips, often going over to “educate” her. Bow chicka wow wow.
61. And I Oop
Poor Earl Pulteney. Little did he know, getting his hot young girlfriend a job at court meant that she’d be surrounded by London’s most eligible bachelors. Elizabeth immediately became the hot girl at the court. All the eligible young men came out of the woodwork, including Augustus John Hervey. Not only was Hervey a prominent Navy lieutenant, he also came from a noble family, and Elizabeth and John immediately hit it off. Chudleigh couldn’t have known it then, but she’d regret that day for the rest of her life.
62. The Proposal
Hervey was so into Elizabeth that he cancelled his next voyage and put his career on the line for a shot at her heart. He went over to Elizabeth’s residence and asked her to marry him then and there. Elizabeth, equally young and short-sighted, said yes. The couple got married in a secret moonlit ceremony in August of 1744.
63. Hot Mess: Activate
After secretly marrying Hervey, Chudleigh returned to court with a real devil-may-care attitude. One of the most famous stories about Elizabeth Chudleigh comes from this time. Chudleigh, clearly feeling herself, shows up at a masquerade in a startlingly revealing garment. She was dressed as a figure from Ancient Greek mythology, Iphigenia, but she caused a total court scandal.
Apparently, while some flimsy beige silk provided technical cover, Chudleigh’s breasts were fully visible.
64. Brains and Beauty
On the same night, King George II approached the scantily-clad beauty and requested to handle the goods. Chudleigh put on her best dulcet tones and replied that she knew an even softer place. Then she coyly placed the King’s hand upon his own bald patch. This girl's got moves.
65. Secretly Yours
For a while, Hervey and Chudleigh managed to keep their marriage both functional and secret—but soon it all came crashing down. The marriage failed, which meant that Chudleigh was back where she shone; on the market. If she knew anything, it was how to hustle. She surveyed the men around her and chose her target, Evelyn Pierrepont, the Second Duke of Kingston.
66. Game, Set, Match
To everyone’s surprise, not only did Chudleigh successfully sink her claws into Pierrepont, the duo actually fell in love, and she became his mistress. Even though Pierrepont was known for being shy and homegrown, the beauty and the geek got along just famously. I guess opposites attract, especially when one opposite has a butt ton of money.
67. A Voice From the Past
While enjoying a glamorous life with her new man Pierrepont, all Chudleigh's lies unraveled. Her ex-husband Hervey reappeared. He had a new reputation as “The English Casanova” and evidently, he wanted to play the field. So, to her horror, he started asking for an honest-to-God divorce.
68. Teaming up
There was just one problem: Getting a divorce would mean everyone finding out about the whole secret marriage thing. This wasn’t good news for either Chudleigh (who wanted Duke Pierrepont for a husband) or Hervey (whose latest girlfriend didn’t get why he wasn’t popping the question). That’s when the exes decided to hatch an ingenious plan.
69. Keep Your Friends Close
Chudleigh and Hervey worked together to get out of their marriage with minimal fallout. They decided that Hervey would tell everyone they were married, then Chudleigh would charge Hervey with slander. When they went to court, Hervey would pretend like he couldn’t find the paperwork, which would make it look like he was lying and Chudleigh was an innocent victim.
After the theatrics, the court would declare that the duo had obviously never been married. Pretty clever, right?
70. Happiness Is Fleeting
Chudleigh and Hervey pulled off their scheme and Pierrepont put a ring on Chudleigh. It looked like a happy ending, but ha! Of course it wasn't. In 1773, Pierrepont passed away and everything fell apart again. Pierrepont's will gave everything to Chudleigh with the idea that when she died, it would all go to Charles Medows, his younger nephew. Well, the older nephew, Evelyn Medows, was pissed. He decided to hit Chudleigh where it hurt most.
71. The Event of the Year
The ticked-off nephew presented enough evidence of Chudleigh’s double marriage for the Grand Jury to take the case and, wouldn't you know it, the court found Chudleigh guilty of bigamy. But that’s not the worst part. She knew it was all her fault. You see, back in 1759, she had actually rounded up a bunch of witnesses to her secret marriage and made them sign a document. Why the heck did she do that? She thought she might be able to inherit some of Hervey's money.
Spoiler: She didn't, and now she was paying for it.
72. Scam Me Once
After Chudleigh heard that the court found her guilty of bigamy, she planned one final scam. She got out her most ostentatious carriage and told the driver to cart her around town for hours. Or so it seemed: Chudleigh wasn’t in the carriage at all. She just wanted to give the appearance of going on a bender while she did something far cleverer.
Our girl actually packed up all her jewels and got the heck out of town. She spent the rest of her life gallivanting around France. Respect, Chudleigh.
73. Pompadour and Circumstance
Madame de Pompadour was deeply influential and beloved in her time. Despite being a married woman herself, she not only shared the bed of the king but his power. Scholars consider her to be one of the most powerful mistresses in history for a reason. She's why the "pompadour" hairstyle got its name, and that's just the tamest of her many achievements.
74. Let’s Get Married...ish
When Pompadour was 19 years old, she married Charles Guillaume Le Normant d’Ettioles. They'd remain married for the rest of their lives, but only on paper. Our girl Pompadour was determined to do a little better than Charles. She had her eye on the King of France himself.
75. Look Over Here!
Pompadour first tried to get the attention of King Louis XV when he was on a hunting expedition in 1744. The hunt was held nearby her own estate, and so she was allowed to follow the king’s entourage from a distance. However, she wasn’t content with that arrangement, so she purposefully rode in the king’s path several times. To make doubly sure he couldn’t miss her, she was wearing a different-colored outfit each time she rode past him. Subtle!
76. Second Meet-Cute
Pompadour was given her first formal invitation to the Palace of Versailles when a masked ball was held on February 25, 1745. The ball was held to celebrate the wedding of the Dauphin Louis de France to Maria Teresa of Spain. Louis outdid everyone else by dressing up as a yew tree, which was apparently such an ambitious costume that it required seven other courtiers to pull it off.
Pompadour attended while dressed as Diana, who was the Roman goddess of the hunt, a fitting reference to how she’d first met the king. We can assume that Louis appreciated that reference, because he chose that ball to unmask himself to her and publicly declare his affection for Pompadour. It was a milestone for their relationship.
77. Moving up in the World
Pompadour became the king’s official mistress by March of 1745, when she took up her abode in the Palace of Versailles. Her apartment was right above the king’s, in case anyone was confused by her reasons for being there.
78. Jolly Good!
Until 1881, the British Army had a regiment called the Regiment of Foot. They were nicknamed the “Pompadours” as their uniforms had purple facings. Purple had been Pompadour’s favorite color, though being soldiers, the men of the 56th spread the rumor that it had also been the color of her undergarments. Naughty, naughty.
79. The Mistress and the Queen
You’re probably thinking about how awkward and toxic Pompadour’s relationship with Louis XV’s wife, Queen Marie Leszcynska, must’ve been. However, their relationship was completely cordial, if the accounts are to be believed. Pompadour eagerly tried to make friends with the queen on their first meeting, and the queen accepted her graciously.
At the height of Pompadour’s influence, she was raised to serve as a lady-in-waiting to Queen Marie, which gave her a lot more power than she already held by that point.
80. Speaking of Cup Size…
One long-standing legend is that the shape of the French champagne glass, also known as the coupe, was originally modelled after the size and shape of Pompadour’s breast. It remains unconfirmed whether this is true, but the story has endured across history.
81. The Original Heartthrob
He was born—deep breath now—Rodolfo Alfonso Raffaello Pierre Filibert Guglielmi di Valentina d'Antonguella, and came to be known as the Great Lover, the Latin Lover, the Sheik...or simply Rudy to his friends. One of the first male heartthrobs of cinema’s silent era, Rudolph Valentino’s short life was filled with astronomical success and fame, but also plagued with toxic criticism, tumultuous love affairs, bad fortune, and poor health.
82. On His Way to Steal Your Girl
Valentino made a big impression on a screenwriter named June Mathis. After seeing him in an early screen role, she insisted he perform in her movie, The Four Horsemen of the Apocalypse. Mathis' instincts were right: After seeing the early cuts, the movie's director Rex Ingram decided to give Valentino even more screen time. He asked Mathis to write a brand new scene where Valentino’s character steals another man’s woman, and together they dance the tango. With this scene, the "Latin Lover" was born.
83. Sign of the Times
Valentino was active at a time when traditional modes of masculinity were clung to with an icy grip, and gay-bashing was rife. Despite persistent speculation and rumors about his sexuality—along with the notion that his relationships with Acker and Rambova were merely “lavender marriages”—by all credible accounts, Valentino was straight. The relentless scrutiny left him feeling constantly insecure about his masculinity.
84. The Fatal Collapse
During the press tour for his final film, The Son of the Sheik, Valentino collapsed and was hospitalized due to a perforated ulcer. Fans stood outside Polyclinic Hospital in New York for a week, but it was no use: Their beloved Valentino succumbed to infection around midday on August 23. He was only 31 years old when he died. After his death, Valentino's reputation as a heartthrob really solidified.
85. Funeral Hysterics
Valentino’s passing left mourners in a state of inconsolable grief. Over 100,000 desolate mourners lined the streets outside the church where his funeral service was held, there were riots, and a number of suicide attempts (by both men and women) were reported.
86. Unlucky in Love
Valentino impulsively married his first wife, actress Jean Acker, in 1919, two months after they met. Acker had only seemed to be interested in women at the time, and had reportedly been involved in a love triangle with actresses Grace Darmond and Alla Nazimova. Whether or not she was ever actually romantically interested in Valentino is unclear, but we do know that she regretted marrying him immediately.
Acker locked Valentino out of their hotel room on their wedding night, the couple separated soon after, and Acker moved back in with girlfriend Grace Darmond soon after. They finalized their divorce in 1922, but ironically became good friends afterward.
87. Not-So-Smooth Sailing
Valentino's second marriage was even rockier than the first. Natascha Rambova was not popular with a number of Valentino’s friends and the marriage disintegrated to the point where Rambova was eventually banned from his film sets. That bad blood didn’t end when he died, and he left behind a cruel tribute to her. Valentino passed away a year after their divorce, but luckily for him, he’d updated his will in time—and in that will, he left her one single dollar bill. Ouch.
88. The Woman in Black
For decades after Valentino’s death, a veiled woman in black has arrived at his tomb on the anniversary of his death to place a single rose on his grave. The identity of the woman was a mystery at first, until it was revealed that the whole thing was—you guessed it—a publicity stunt, this time cooked up by press agent Russel Birdwell in 1928. When this got out, several copycats vied to be the new “Woman in Black” and the tradition continued. Film historian Karie Bible is the most recent to have taken up the mantle.
89. Let's Take a Selfie
Virginia Oldoini—better known to history as the Countess of Castiglione—might be the original Queen of the Selfie. The Italian aristocrat’s legendary beauty, espionage missions, and endless train of scandalous lovers were documented by her photographic adventures. Of course, the Countess didn’t get by on looks alone, though they certainly helped her from time to time, especially when she needed to ensnare a wealthy man or two.
90. Sow Your Wild Oats Before You Spit Them out
Virginia Oldoini earned her famous name and title through marriage. At the age of 17, she was wed to Count Francesco Verasis di Castiglione, who was 12 years older. They only had one child, a son named Giorgio. Right before her arranged marriage to this older man, Oldoini embarked on an affair with a naval officer, which suggests she desired things beyond domestic bliss from the beginning.
91. Belle of the Ball
Oldoini followed her husband to the court of King Victor Emmanuel II of Sardinia-Piedmont (today we just call it “Italy”). The Countess quickly outshined her hubby, winning ministers and courtiers alike over with her charm. In fact, she was known to the court as “la divina contessa.”
92. CIA: Cute Intelligence Agency
Oldoini’s true career, however, began when she was “discovered” by her cousin, Count di Cavour. Her first gig wasn’t for modeling: It was for espionage. Cavour saw the value of Oldoini’s charms and singled her out as the perfect candidate to deploy to the Parisian court of Napoleon III. Castiglione soon became the French ruler’s mistress.
93. I’m Keeping the Title
Oldoini’s husband did not take well to his wife becoming a spy and seducing the French emperor. Their very public affair led him to demand a marital separation. By 1860, Oldoini’s affair with Napoleon III had soured, and she had completely lost favor at his court. The reasons for her sudden fall from grace remain a private mystery.
Nevertheless, she would address herself as the “Countess” for the rest of her days…
94. The Eyes Have It
To no one’s surprise, the Countess of Castiglione met the Eurocentric beauty standards of her day. She is typically described as a wavy-haired blonde with pale skin, delicate features, and an oval face. According to lore, her eyes could change color from green to an almost supernaturally blue-violet. Pretty handy trick to have if you’re a model and spy.
95. This Little Piggy Asked to Be Censored
Some of Oldoini’s photos put her in “risqué” positions (at least by 19th century standards). In such scandalous poses that—gasp!—exposed her bare feet and legs, her head is cropped out.
96. Too Hot to Be a Writer
At one point, the Countess tried her hand at writing. Her autobiography was to be humbly titled The Most Beautiful Woman of the Century. Tragically, she never completed the book. She was probably too busy being beautiful.
97. Twelve Hours of Hard Labor
At the height of her fame as a courtesan, the Countess could still rake it in. Reportedly, Richard Seymour Conway offered 1 million francs for just 12 hours of her “company.”
98. She Wears Her Heart (and Your Hubby) on Her Sleeve
Dressed in her signature Queen of Hearts gown, Oldoini once scandalously entered a royal ball on the arm of her (married) lover, Emperor Napoleon III, right in front of his wife. At least the empress got a good snipe in. The spurned wife reportedly gave Oldoini’s sexy outfit a once-over and coolly told her, “The heart is a bit low, Madame.”
99. Time Management Queen
Catherine the Great is regarded as one of the greatest rulers in Russian history, and she was the longest-ruling female leader in the country’s history. Her impact was so great that the period of her rule is known as the Catherinian Era and the Golden Age of the Russian Empire. Not only did Catherine lead her country to greatness, she still found time for a bevy of scandalous conquests.
100. Where's Maury When You Need Him?
Catherine and her husband Peter didn't have the best marriage. He was notoriously childish and would rather play with his toys than go to bed with his wife. It took eight long years before the couple had a son, leading to speculation that the baby's father was actually a military officer named Sergi Saltykov. We'll never know for sure, but Catherine and "Peter" had three more children and historians don't think any of them were actually Peter's.
101. Lofty Ambitions
After the Empress' death in 1761, Catherine’s husband Peter ascended to the throne, but his policies were very unpopular. Soon enough, there was a plot to unseat Peter and place his son Paul on the throne, with Catherine as Regent. However, Catherine did not want to fade into the background. With the help of her lover Gregory Orlov, she gathered support and declared herself the sole ruler of Russia.
102. Conspiracy, Maybe
Few coups are as epic as Catherine's. She arrested her own husband, forced him to give up his power, but the worst was yet to come. A few days after abdicating, Peter was murdered by one of Catherine's co-conspirators. The exact role she played in his death has never been proven, but it’s very possible that she arranged it. Ice cold, Catherine.
103. Pays to be her Lover
Catherine was extremely generous towards her lovers. She would give them titles, lands, palaces, and even people, once giving a lover 1,000 serfs. But becoming a lover of Catherine the Great was no easy task. Before sealing the deal, potential suitors had to pass an intimate test. Prospective gentlemen had to first satisfy Catherine's lady-in-waiting, Countess Praskovya Aleksandrovna Bruce. Unsurprisingly, this arrangement made for a lot of drama.
In 1779, an advisor led Catherine into a room where Catherine's latest lover, Ivan Rimsky-Korsakov, was having intercourse with Bruce. The lover was sent into exile, and Bruce followed him. Bruce was relieved of her duties as lady-in-waiting shortly after.
104. Myth Busting
There is just as much misinformation (or unprovable claims) as information on Catherine II. Some juicy wish-they-were-true examples: that she kept her hairdresser in a cage to keep her wig a secret and that she advocated for having sex at least six times a day, claiming that it helped her relieve her insomnia. Neither of these claims have been verified by historic record.
105. An Erotic Collection
Catherine’s public and private images were two very different things. She secretly collected sexually-charged furniture, and even had an erotic cabinet adjacent to her suite of rooms. German soldiers who raided the palace during WII claimed to have stumbled across the erotic boudoir full of furniture, and photographed it. Most of the photographs were lost in the war, and those that remain are believed to be the only surviving evidence of the furniture.
The furniture wasn't the only thing naughty in the Muscovite palaces--Catherine also employed full-time foot ticklers. A long-standing tradition for Russian royalty, foot ticklers would sing sexual ballads while tickling their master's feet to provide relaxation and arousal.
106. Died a Mundane Death
Gossip had a tendency to follow Catherine wherever she went, and continued to follow her even after her death. Her enemies at court spread rumors about her death, with some claiming she’d died on the toilet, and others that she’d died while having, um, relations with a horse. None of those were true: she died in her bed the day after suffering a stroke, at the age of 67.
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