Kings and queens live lives of unchecked privilege and luxury, with an entire court ready to follow their every whim. That’s boring. What about the ones who had to fight tooth and nail to make it to the top, using their looks, charm, and sheer force of will to burst open the palace gates—and knock down the royal bedroom doors? They’re at least 1,000 times more fascinating. These royal mistresses lived lives filled with struggle, scandal, and dark, twisted secrets. Whether they did it for money, power, or—gasp—even love, one thing is for sure: their stories are absolutely unforgettable.
1. Madame De Montespan, The False Queen Of France
With her good looks and charm, Madame de Montespan could’ve easily hopped into bed with the notoriously lustful King Louis XIV. But she wasn’t just in it for the bedroom play. No, she wanted a lot more than that—and she knew that patience would be the name of the game. So, she remained at a distance and watched as her friend Louise de la Vallière enjoyed the fruits of being the king’s lover.
Throughout the next two years, Madame de Montespan appeared modest and unassuming—but really, she was waiting to make her next, cunning move.
2. She Had Great Timing
Louise de la Vallière suspected that her old friend Madame de Montespan had set her sights on the king, but she was comfortable in her position and didn’t worry about anyone supplanting his affections. It was a fatal mistake. In late 1666, both the queen and Louise de la Vallière were pregnant at the same time. The king found himself a little lonely…and who was there to entertain him but Madame de Montespan.
When starting a romance with the king, many of Louis XIV’s mistresses found themselves in over their heads—but not Madame de Montespan.
3. She Knew How To Satisfy
As mentioned before, Louis XIV was notoriously libidinous with his mistresses. Well, he’d more than met his match with Madame de Montespan. Courtiers said that they did the deed at least three times each day and that sometimes the king wouldn’t even wait until her entourage left the room to get things started. But that’s not the worst part. Even when Louis XIV had two mistresses at a time, it still wasn’t enough.
According to courtiers, he would often finish his “encounter” with Madame de Montespan, only to then take one of her ladies-in-waiting while she got dressed again. Somehow, that’s not even the most scandalous part of their relationship.
4. They Turned On Her
Madame de Montespan’s exuberant personality and hold over the king rubbed a lot of people the wrong way—and it came back to bite her. Poison was the subject of the day at the French court, as one of their own had recently been executed for giving poison to her family. Just like the Salem witch trials, people began accusing anyone and everyone of poison plots.
When Parisian investigators began detaining those they suspected of selling poisons and performing black magic, they began to spill names—and one kept coming up: Madame de Montespan.
5. The Stories Were Jaw-Dropping
One witness said that Madame de Montespan collaborated with the most notorious poison dealer in the city, La Voisin, and that they used black magic to keep the king’s love. There were tales about praying to the devil and a black mass performed by a priest over de Montespan’s undressed body. Somehow, that wasn’t even the craziest story. One claimed that de Montespan and La Voisin had been sacrificing babies and putting their remains in Louis XIV’s food for over a decade. Yikes.
These were obviously quite far-fetched—but the fallout was impossible to avoid.
6. She Was At The Center Of It All
The courts declined to pursue these accusations against Madame de Montespan, and nothing was ever proven. Still, the damage was done. If Louis were to eject Madame de Montespan from the court, it would only confirm the suspicions about her involvement. After her downfall, Madame de Montespan stayed in the French court for a whopping—and likely painstaking—ten years, and watch as her former lover fell for another woman.
Finally, she left and lived her final years first at a chateau Louis had given her, and then at a convent—presumably, trying to atone for her sins. Not every royal mistress lived to feel that type of regret, though…
7. Nell Gwyn: The X-Rated Mistress With A Quick Wit
Nell Gwyn’s life was like a racy Cinderella story. Born in abject poverty, she first became a professional actress. Scrappy Nell then elbowed her way past legendary beauty Louise de Kerouaille to get into King Charles II’s bedroom. Elegant and poised, Louise sneered at her low birth—but Nell got revenge in a truly vicious manner. The former orange wench knew how to hit where it hurt, and she often insulted Louise by calling her “Squintabella” and “The Weeping Willow,” making fun of her tendency to cry.
Unfortunately, Charles II wasn’t exactly a one-mistress type of guy, and she frequently had to deal with romantic rivals. Sometimes, she had to deal with people mixing her up with them, and she did not appreciate it…
8. She Knew How To Make A Statement
According to lore, Nell Gwyn used her signature wit to defend herself from an anti-Catholic mob in 1681. While she was passing through Oxford, a crowd besieged Gwyn in her carriage, mistaking her for Louise de Kérouaille, another one of the king’s mistresses. As they screamed at “the Catholic wh-re,” Gwyn’s answer was unforgettable.
She popped her head out of the carriage window and assured the mob, “Good people, you are mistaken; I am the Protestant wh-re!” The crowd cheered and allowed Nell to carry on her way. She never really let her romantic rivals bother her—but she had one sore spot.
9. She Knew How To Make A Threat
Nell Gwyn happily bore King Charles II a son. But when he refused to acknowledge the child, she demanded that he make the boy an Earl. After all, he’d given another one of his illegitimate children a title. According to one source, she wore him down with incessant needling—but some historians believe the true story is much darker. In this tale, she held her baby out of a window and threatened to drop him unless King Charles elevated him.
Instinctually, King Charles cried, “God save the Earl of Buford!”…and that’s what they chose for his title! After all, Nell had been an actress, so she had a flair for the dramatic. There’s a lesson to be learned there—but “don’t mess with actresses” is, unfortunately, wisdom that did not get passed down through the English kings.
10. Lillie Langtry: The Jersey Lily
Victorian England was full of scandalous figures, but none of them held a candle to the infamous Lillie Langtry. She made her name as the stunning Jersey Lily, and soon enough she shared her bed with princes, soldiers, and millionaires…even though she was married. Though she came from humble beginnings, Lillie Langtry was not someone you wanted to mess with.
She climbed her way up the ladder into high society—and into a future king’s bed. That’s right, Lillie was one of the early mistresses of none other than Edward VII. But she quickly overstepped her boundaries…
11. She Met The Queen
One of Langtry’s wishes was to meet Queen Victoria—a bold move, considering the affair with her son! The prince did arrange the meeting though, and the queen wasn’t exactly happy to be meeting Langtry. In fact, the monarch was rather cold to her. That didn’t matter though: Meeting the queen meant Langtry was now flooded with invitations to meet some of the most important people in London.
However, her quick rise to fame meant an even quicker crash down to rock bottom.
12. She Couldn’t Keep Up
Langtry’s popularity started to wane when Sarah Bernhardt, a French stage actress, arrived in London. And then, of course, there was her romance. They called Edward VII “Dirty Bertie,” not “That guy with a wife and just the one mistress.” Edward lost interest in their affair and Langtry found herself nearly penniless, abandoned by her husband and lover. Well, she may have been down, but she wasn’t out just yet.
13. She Had A Secret Child
Prince Louis of Battenberg was the next prince to fall victim to Langtry’s charms—but their affair had a dark end. When Langtry realized she was pregnant, she knew the question of the child’s paternity would come up. She decided to move away to hide the pregnancy from the circles of gossiping society ladies in London. The baby, she decided, would be born in secret…and she got help from an unexpected source.
Edward VII came to her aid and paid for her to go to Paris. Later, when she got into acting, he was one of her patrons. As exes go, he was a gem—but not every royal mistress got out of their affair with such a clean break. Some paid with their lives.
14. Marie Anne De Mailly-Nesle: The Manipulative Mistress
The De Mailly-Nesle sisters were known for their scandalous affairs with the King of France, Louis XV, but none as much as Marie Anne, the youngest sibling. In fact, Marie Anne was the most manipulative and ingenious woman in her family, and she had absolutely no qualms about squishing her sisters underfoot on her way to the top—and her sisterly betrayal was utterly brutal.
After positioning herself as the king’s next potential chief mistress, she asked him to essentially banish her sister Louise Julie. Unfortunately, for a ruthless temptress like Marie Anne, the royal world was a dangerous place. It was only a matter of time before enemies arrived on her doorstep, raring to tear her apart.
15. She Should’ve Known Better
Marie Anne actually should’ve seen it coming. Before she got together with Louis XV, another one of her sisters, Pauline-Félicité, had reigned as mistress supreme…but not for long. She died giving birth to the King’s illegitimate son, and then, to add insult to injury, a mob viciously mutilated her body. Now, if anything, this might seem like one big red flag—a flashing warning sign saying, “Don’t Become A Royal Mistress.”
But of course, Pauline-Félicité’s gruesome end wasn’t enough to discourage Marie Anne. Nope. Not one bit. She went straight for royal gold—and her plan to seduce Louis XV was, let’s say, unconventional.
16. She Made Him Work For It
Marie Anne had watched two of her sisters make their way into the king’s bedroom—but she wanted to outdo them both and make sure that Louis XV knew she was the most desirable de Mailly-Nesle sister, so she took an alternate route to seduction. Marie Anne was the very first woman to reject the King’s advances, playing hard to get and proving that she was the greatest temptress around. But that wasn’t all. Before she even deigned to slip out of her gown and please the King, Marie Anne had a list of conditions for him.
Marie Anne milked that man dry, asking for dispensations, titles, properties, you name it. And it all worked out for her—at least, at first.
17. She Was A Pawn
Marie Anne thought she was the smart one—even smarter than the king himself. But on the sidelines, a number of courtiers were playing a vicious game of thrones, guiding the king’s hand. She thought she was in charge, but her so-called “friends,” among them the Duc de Richelieu, were using her to sway the king. There was just one problem. Marie Anne could drive the king absolutely mad with one sidelong glance and he was undoubtedly obsessed with her.
But when it came to exercising political influence, she had ZERO game. She was either too subtle or too obnoxious. Still, in spite of herself, she eventually convinced Louis XV to join the hostilities surrounding the Austrian Succession. It wasn’t exactly a glowing success, however.
18. She Had Scandalous Tastes
Having sent the King to battle, Marie Anne and her sister, Diane Adélaïde, wanted to show their support by paying him a visit near the front in Metz. It was a decision that would shatter Marie Anne’s entire reputation. While there, a rumor spread that Marie Anne occasionally liked to pique the King’s “interest” by offering a ménage à trois with her sister. This shouldn’t be surprising to anyone following along, but it still wound up causing a national scandal.
The King, in poor health, sent Marie Anne and her sister home and called for his wife. Still, as soon as he recovered, she wormed her way back into his heart…and bed.
19. She Had A Horrifying Revelation
Marie Anne’s return to greatness was tragically short-lived. Soon after she returned to court, she began experiencing convulsive aches and cramps. The violently ill Marie Anne retired to her bed-chamber in the hopes of a rapid recovery, but something was seriously wrong. As she lay in bed, writhing in pain, she had a revelation so horrifying—it’s impossible to forget.
20. She Suspected Foul Play
Even in distress, Marie Anne made a vicious claim. She believed that she’d been poisoned. This was surely foul play. Unfortunately, no amount of accusations could save this cunning mistress from her inevitable end, and on December 8, 1744, she passed. Five days later, Marie Anne’s body was laid to rest without ceremony in the Parisian Church of Saint-Sulpice.
Unfortunately, even beyond the grave, the King still managed to insult her.
21. She Was Just Another Mistress
The playboy King wasted to no time in moving on. He made it clear that Marie Anne was just another drop in the ocean. After all, a mistress was always replaceable. And more than that? He didn’t have to look far. His next conquest was none other than Diane Adélaïde, Marie Anne’s sister, and then, a few months later, he found a brand new mistress—the infamous Madame de Pompadour. And boy, was she a doozy…
22. Madame De Pompadour: France’s Most Powerful Mistress
It’s no wonder that Madame de Pompadour climbed the ladder all the way up to the king’s bedroom. It was meant to be! When Pompadour was a little girl, her mother took her to a fortune teller, who made a stirring prediction. The fortune teller allegedly said that the little girl “would one day reign over the heart of a king.” Her mother seemed to believe it, because she basically became the 18th-century version of a stage mom, grooming her kid to be the king’s mistress. To say it worked would be an understatement…
23. She Was More Than Just A Pretty Face
While some would scoff at the idea of a mistress doing anything productive—and indeed, she had many enemies in her lifetime—Louis XV’s lover Madame de Pompadour proved to be deeply influential and beloved in her time. She not only shared the bed of the king but also shared his power. So, how’d she capture his heart? Well, to quote Hannibal Lecter, “We begin by coveting what we see every day, Clarice.”
Madame de Pompadour made sure she frequently crossed paths with the king, and every single time, she was dressed up to the nines. Finally, Louis XV publicly declared his affection for her at a costume ball—but his timing was less than appropriate. The party was in celebration of his son’s new marriage. Whoops.
24. Their Relationship Was Unconventional
While on the outside, their relationship was happy and healthy, modern historians now know that the couple hid a dark secret behind bedroom doors. From 1750 onwards, Pompadour stopped sleeping with Louis XV. They no longer actually made love. Historians have attributed this shift to Madame de Pompadour’s very poor health.
Over the years as Louis XV’s mistress, she had three miscarriages, and also “suffered the after-effects of whooping cough, recurring colds, and bronchitis, spitting blood…as well as an unconfirmed case of leucorrhoea.” However, her bond to Louis did not dim—even though their lack of bedroom activity caused his chronic case of “wandering eye” to act up again.
25. She Played It Cool
Louis was not a one-woman man. During his affair with Pompadour, he sated his physical desires on the side with casual sojourns in his “Parc-aux-Cerfs” or “Stag Park,” a building specifically for the king’s affairs. Rumors swirled that Pompadour was the mastermind behind the king’s debauched palace, gleefully setting up her lover with a harem of women.
In reality, Pompadour just accepted the king’s side pieces, especially after her health issues caused her to retire from bedroom activities. And they really were serious health issues, not just her not being “in the mood”…
26. Her Ending Was Tragic
In 1764, Madame de Pompadour began to feel unwell. When the doctors examined her, they had terrible news: the king’s great love had tuberculosis. Louis looked after Pompadour as best he could, but ultimately she succumbed to her illness and passed away at the place she loved more than anywhere else: Versailles. She was just 42 years old. After Pompadour’s loss, tributes poured in from all over France.
King Louis XV described their bond not just as a passionate romance, but a “twenty-year friendship.” However, shortly after Pompadour was gone, the king had no choice but to betray his great love…
27. He Was Missing In Mourning
Although the king deeply grieved at Pompadour’s death, court protocol forbade him from attending her funeral. After all, Pompadour had been born as Jeanne Poisson, a middle-class woman. Because of this inconvenient fact, she was too low-ranking to deserve a royal funeral attendance, even if the King himself was her life partner.
When it comes to dark ends and heartbreaking betrayals, though, few stories beat that of Gabrielle D’Estrées…
28. Gabrielle D’Estrées Was The Duchess Of Filth
There was no one in 16th-century France who was more powerful—or more scandalous—than Gabrielle d’Estrees. An official royal mistress to one of the most notorious kings of France, Henry IV, Gabrielle more than earned her nickname “The Duchess of Filth.” The racy nicknames started early, actually. See, Gabrielle’s family was large, with 11 children in total and seven daughters.
The women in the brood all started to get a bit of a reputation around town, leading a French writer to give the gaggle of girls the moniker “The Seven Deadly Sins.” Yet Gabrielle’s exploits would blow her sisters right out of the water.
29. She Had A Scandalous Meet-Cute
Around 1590, Gabrielle met King Henry of Navarre, the nominal King of France. While some say that one of her other lovers introduced her to Henry, it was obvious that sparks flew between the two immediately. Even so, Gabrielle reportedly resisted the monarch’s advances for six long months—and she had a very good reason to hesitate.
30. She Liked Bad Boys
Gabrielle knew she needed to watch out, because Henry was the 16th-century bad boy. Raised Protestant, he refused to convert to France’s traditional Catholicism when he took the throne, pitting him against the country’s powerful Catholic League and embroiling him in a mighty battle for the crown that he was still fighting for when they met.
Except that was just his public rebellion—his bedroom life was downright dirty.
31. She Was Into Older, Married Men
First off, when Gabrielle met and started flirting with Henry, he was a whopping 37 years old while she was, need I remind you, still 17. As you might be able to guess, Henry was a primo scuzzbucket. His libido was notorious, and when he wasn’t starting religious feuds, he was usually seeking out yet more mistresses or, better yet, risqué “encounters” with strangers. And now, he set his sights right on Gabrielle…
32. She Was A Diplomatic Star
Their affair began in earnest, and Gabrielle quickly gave the king something his wife never had: a child. With the birth of her son Cesar, Gabrielle gained unprecedented influence over the court. She quickly popped out another two kids, which made the middle-aged Henry IV finally see the writing on the wall. He needed an heir, and his marriage wasn’t going to produce one. He had a difficult choice to make—and his hesitation would end in disaster.
33. She Was An “Almost Queen”
In 1599, after years of trying, King Henry IV finally made some progress in gaining an annulment from his wife Margaret, who was probably just as happy as him about that. On Mardi Gras that year, the king asked Gabrielle d’Estrees a scandalous question. Well, scandalous in the eyes of France: He asked her to marry him. In true dramatic fashion, the king proposed with the ring from his coronation, AKA the one he had “married” France with. Then, of course, she got pregnant yet again.
At this point, Gabrielle couldn’t possibly get any more powerful…so how did it all go so wrong, so fast?
34. She Suffered An Immense Tragedy
On April 9, 1599, Gabrielle suffered a horrific attack. Something in her pregnancy shifted, and in a haze of pain, she gave birth to a stillborn boy. This must have been tragedy enough, but then attendants realized Gabrielle herself was pale and ill. Afraid for her life, they sent for King Henry IV, who was away from Paris at the Château de Fontainebleau. But as the night wore on, their fears turned to terror.
35. Her Symptoms Were Gruelling
According to attendants who saw Gabrielle as she lay sick in bed, her face turned nearly black from the illness that was ravaging her body, and it made her face so deformed that she was barely recognizable. Indeed, reports indicate that Henry’s entourage, learning of Gabrielle’s state, stopped on the road to delay the king and prevent him from seeing her this way.
After fighting for her life through the night of April 9th, Gabrielle d’Estrées perished on the 10th, before King Henry was able to give her one final goodbye. She was only 26. But the heartbreak didn’t stop there…
36. Her Lover Desecrated Her Memory
Although King Henry IV did grieve Gabrielle, he also saw the “bright side” of her demise insultingly fast. Henry spent his mourning period for Gabrielle cavorting around and living it up in his own private brothel. Indeed, it was around this time that he met the woman who would become his next big mistress, the teenaged Henriette d’Entragues. Almost instantly, Henriette tried to ruin Gabrielle’s memory.
37. She Got A Replacement
If Gabrielle was ambitious, her successor Henriette was darn near starving for power. The upstart girl, who came from a long line of royal mistresses, usurped Gabrielle’s best-laid plans and tried to install herself as the Queen of France, all before Gabrielle’s body was cold in the ground. Henriette even obtained a WRITTEN PROMISE from the king to marry her the minute he was over his ex.
Did Henry do it? Nope. Maybe if he had, Henriette would’ve had a legacy as memorable as that of Gabrielle D’Estrées—but it’s unlikely, considering just how unforgettable Gabrielle could be…
38. She’s In A Famous Painting
Before she passed, Gabrielle got a very risqué portrait made of herself: “Gabrielle d’Estrées et une de ses sœurs,” by François Clouet, which now sits in the Louvre museum in Paris. In the painting, Gabrielle and her sister sit in a bath. Gabrielle holds Henry’s coronation ring in one hand while her sister…pinches Gabrielle’s nipple.
If that sounds vaguely familiar, it’s because it’s an extremely famous—and famously bizarre—painting. I mean, is there any better legacy than this? There might only be one other royal mistress as deranged as her…
39. George Villiers: The King’s Lover
Who says a royal mistress has to be a woman? EQUAL OPPORTUNITY, PEOPLE. See, It wasn’t uncommon for a ruler to have a “favorite” from among their courtiers—but there was something unusual about King James I of England‘s favorites. Despite the fact that James had a wife and family, he also liked to sleep with men on the side. One of his favorites, Robert Carr, had also been his regular lover. Just as their relationship ended, George Villiers came to court.
George was tall, athletic, and hopelessly handsome. He charmed whoever he met, including King James. Before long, he held a special place in the king’s heart—maybe a little bit too special, because he almost brought the entire country down around him
40. The King Really, Really Liked Him
Over time, King James’ love for George developed into something on a whole other level. The King called him his “sweet child and wife” and made it clear to everyone that he loved him more than anything in the world. James loved Villiers enough to allow him tremendous influence over the kingdom. Over time, Villiers began to take advantage of his unique position in increasingly bizarre and inappropriate ways—and the crazier his actions became, the more the public started to hate him.
41. He Used The King
Little by little, Villiers began using his power to enrich himself, his family, and his friends. He accepted bribes and inappropriate gifts, misused public funds for his own lavish desires, and tried to create monopolies wherever it would benefit him to do so. He also unintentionally ruined the king’s son’s marriage negotiations in Spain, and the Spanish royals did not take it lightly.
They actually asked the British Parliament to have Villiers executed over the incident! Still, George stayed on his feet…at first.
42. He Lost His Lover
George’s dumb luck had to run out sometime, right? One would expect the death of King James I to spell the end for him, but not so. James’ son Charles took over, and Charles actually may have loved Villiers ever more than his father! Not one other member of King James’ court managed to keep their positions under Charles, except for George. Both kings were putty in Villiers’ hands, and their obsession had devastating consequences.
43. They Were Sick Of Him
Parliament could only take so much of Villiers’ nonsense. In May 1626, they finally decided to try and get rid of him. They tried to impeach him not once, but twice. However, on both occasions, King Charles came to the rescue—but there was one thing he couldn’t rescue him from. After a lifetime of making headlines for ridiculous reasons, the last headlines Villers made were the darkest of all.
While at a pub, an assailant violently attacked George and stabbed him with a knife. Despite his wounds, the Duke attempted to chase after his attacker—but fate had other plans. George Villiers, 1st Duke of Buckingham, collapsed and bled out on the spot. But his story didn’t end there…
44. His Lover’s Son Paid The Price
So, after Villiers was gone, did the people of England finally forgive King Charles and let bygones be bygones? Not by a long shot. Even without Villiers around to screw everything up, Charles remained a terrible king. Eventually, the people of England got fed up enough to do the unthinkable: They captured Charles, tried him for treason, and beheaded him.
To this day, he’s the only English monarch to be toppled by his own people. Sorry, Charles—some people are punished for their bad behavior by their people. Our next example was punished by his own mistress.
45. Mary Robinson: The Vengeful Lover
As the first royal mistress of the future King George IV, the captivating Mary Robinson became an overnight celebrity. Robinson had already gone to debtor’s prison and become a rising star of the stage before the age of 21. And although George was just 17 years old and still a prince the night he first set eyes on tMary, he had already racked up quite the reputation himself.
A rake who loved drinking, gambling, and especially older women, George drove the royal family half crazy with his antics. So when he decided to seduce Mary Robinson, you can bet he stopped at nothing to get her.
46. He Made False Promises
Desperate to get the beautiful star into his bedchamber, George eventually promised her a whopping 20,000 pounds to be his mistress. Well, Mary hadn’t spent months in a debtors’ prison to say no to that, and she finally fell into his arms and separated from her no-good husband. But that didn’t mean it was smooth sailing. The tabloids hounded her throughout their relationship. And then, around 1780, after years of “servicing” George, the Prince of Wales hit her with a crushing blow.
The rakish prince’s wandering eye eventually grew tired of Mary, and he unceremoniously dumped our girl to take up with yet another mistress. Plus, he wasn’t even king yet, so he didn’t have access to that 20,000 pounds he’d promised.
47. She Made Him Pay
Prince George really was going to leave hot girl Mary Robinson high and dry, but he had forgotten one crucial thing. She still had all his steamy letters proving they had a dalliance. Naturally, the whip-smart girl threatened to use them against George—whose family would be none too happy—unless he coughed up at least some of the money he had promised her whn they were lovers.
Sweating through his shirt, the royal complied, giving her a tidy but incomplete sum. But do you think Mary Robinson stopped there? Ha, no. She also got into bed with George’s #1 enemy, politican Charles James Fox. When George was crowned king, Fox negotiated a royal annuity for Mary. Get it, girl. Where Mary found success, our next mistress only found tragic loss…
48. Bessie Blount: The Mistress Who Lost It All
Bessie Blount entered the Tudor court as a maid of honor to Catherine of Aragon, Henry VIII‘s wife—and immediately caused a stir. Henry couldn’t hold back his attraction to the young Bessie—and we mean young. Historians estimate that he was 23 and she was 13 when their romance began. Did this stop Henry? Uh, no. There’s also another reason their relationship was unusual.
Generally, kings took mistresses who were already married, so that if they did happen to get pregnant, they could always pass the baby off as their husband’s child. Bessie had no such protection, and it would come back to haunt her.
49. She Had The Upper Hand
As Catherine of Aragon tried desperately to conceive a male heir for Henry VIII, Bessie Blount enjoyed the fruits of their affair—and then, she got pregnant too. She was still incredibly young, so it was risky. But, when she finally managed to push out the child, the babe shocked all in attendance. It was everything Henry had been longing for: A healthy baby boy. And proof that his wife was the problem, not him.
It was the beginning of the end for Catherine—and thought she didn’t know it, for Bessie too.
50. She Got Dumped
During Bessie’s golden months with King Henry VIII just after the birth of her son, the monarch stopped at almost nothing to bestow honors on her. But soon after the birth, Henry dealt Bessie a brutal betrayal. Very quickly after Bessie went through the trouble of pushing out his whole child, the King suddenly ended their relationship. The reasons behind their split are still mysterious.
It might have had something to do with the fact that since Bessie had proven he could have sons, Henry no longer needed her. However, some historians point to an even crueler reason.
51. She Lost Everything
According to one historian, Bessie’s childbirth may have suddenly made Henry feel repulsed by his mistress. To the king, babies were for wives, not mistresses. Oh, and to add injury to that insult, there was the aftermath of the breakup. Henry quickly tried to marry her off to one of his courtiers—and he picked one whose family had a history of insanity.
Once she’d been pawned off, she was forcefully separated from her son Henry FitzRoy, since he had to be raised within the Tudor household. And then, of course, there was the woman that came after her…
52. He Moved On Fast
After her ousting from Henry’s bedroom, Bessie eventually suffered the loss of her husband and her son by Henry. She even made a brief-but-disastrous return to court before falling ill and dying in her early 40s. At first, her death seemed like a mystery, but historians speculate that she died in the same tragic way her son did: from tuberculosis.
In her final years, she had to watch as Henry took on other wives and mistresses—but it was her immediate replacement that probably stung the most: the notorious “Other Boleyn Girl,” Mary.
53. Mary Boleyn: The Infamous “Other Boleyn Girl”
One historian famously declared that all we know for certain about Mary Boleyn could barely fill up a postcard. Truly, the mysterious “Other Boleyn Girl” will go down in history for her relation to bigger names in Tudor England. She was the sister of Anne Boleyn, the aunt of Elizabeth, and one of only two publicly acknowledged mistresses to Henry VIII.
Thanks to historical fiction and interested Tudor fans, the legend of Mary Boleyn has grown to sordid prominence. How exactly did Mary “snare” a king? And what scandalous act did she commit to earn her famous exile?
54. She Started Early
Mary Boleyn is famed as Henry VIII’s mistress slash sister-in-law—but she got her start as a royal mistress much earlier. While serving as a maid-of-honor to Henry’s sister, she traveled to France and ended up staying. There, she served under King Francis I’s queen, Claude—but she was hiding a dark secret from her so-called friend. It was during this time that Mary was said to have begun an illicit affair with Francis.
Whether or not that’s true—the Boleyn family had a lot of detractors—that’s not what we know her for, is it?
55. They Didn’t Like Her
It’s honestly no wonder that Mary ended up as a mistress and Anne as a wife (though their ultimate fates were both…less than desirable, of course). Her parents seriously played favorites with their kids. Nevertheless, the Boleyns jockeyed for a position for Mary in the English royal court and arranged for a marriage. Little did they know that they’d be sending her down a dark and twisted road.
Upon her return from France, she tied the knot to William Carey and entered the Tudor court—putting her squarely in the notorious king’s sights.
56. Their Relationship Played Out In Secret
It’s not known exactly when it began, but one thing is for sure: soon after her marriage to William Carey, Mary Boleyn began an illicit affair with King Henry VIII. How long did it go on? Did she love him? The answers to many of these questions are mysteries—the pair were actually so discreet that very few accounts of the relationship exist. At first, it certainly came with its own benefits…but eventually, it would come at a great expense to Mary.
57. She Made A Fatal Mistake
Maybe if she hadn’t been keeping her affair with Henry VIII under lock and key, Mary Boleyn could’ve gone to someone with similar experience for advice. Like say, Bessie Blount. Bessie could’ve warned her that having a kid was one of the king’s biggest turn-offs. Unfortunately, Mary didn’t know—and ultimately, after giving birth to her second child, Henry began to turn his attentions elsewhere. And that elsewhere was a little too close to home.
58. He Chose Her Sister
Their affair might have been over, but what Henry VIII did to Mary Boleyn in 1526 had to sting regardless. It was in this year, shortly after the birth of Mary’s second child, that the king began to publicly pursue her sister Anne. If Mary was affected by this quick turn, she didn’t let it show. She had a position in the court to protect, after all—and she’d need all the help she could get, considering what was in store for her.
59. She Was At Her Sister’s Side
Mary’s husband died, leaving her with numerous debts. Neither her ex nor her parents wanted to help her. It was only her sister Anne that came through for her. Years later, Mary Boleyn stood by her sister’s side after Anne married Henry, and was one of Anne’s attending ladies-in-waiting at the latter’s coronation on June 1, 1533. If her sister marrying her ex-lover made Mary feel awkward at all, she never showed it.
60. She Fell Again
Mary Boleyn’s love life had been tumultuous since the beginning—from her early days as the mistress to one king and then another, to her time as a widow. She’d known the advantages (and downsides) to making political matches, but in 1534, something completely unexpected happened to Mary Boleyn. She fell in love—but there was just one problem.
His name was William Stafford, and he definitely wasn’t rich or prestigious enough to openly be with a king’s sister-in-law. Regardless, Mary was determined to be with him—and she’d sacrifice it all to do it.
61. She Couldn’t Hide It
Due to her status—and his lack thereof—Mary Boleyn and William Stafford only saw one option. They eloped in 1534. What should’ve been a glorious and happy day for the couple instead set off a brutal chain reaction that would ruin their life together before it even began. At first, they kept their marriage a secret…but soon enough, the truth came out.
Mary got pregnant, and she couldn’t hide it. When the king and Anne noticed, the consequences were dire.
62. Her Sister Was Furious
The truth was out. Not only had Mary Boleyn secretly married a man beneath her station, she was also pregnant by him. The condemnations were swift and brutal. Anne instantly turned on her sister. Then, her parents disowned her—but the nightmare didn’t end there. Her actions had flagrantly disregarded the king’s authority over her as a courtier, and he was furious. In the end, Henry VIII had his ex-lover and current sister-in-law Mary Boleyn banished from court.
Of course, banishment is way better than what eventually happened to Anne Boleyn not long after. Of all the Boleyns who had dalliances with Henry VIII, Mary was the last one standing. But wait, what do we mean by “all the Boleyns?”
63. He Had A Type—It Was “Boleyn”
Many years before Mary Boleyn’s scandalous affair with King Henry VIII, dark rumors swirled in the Tudor court about her family. Mary’s parents were so power-hungry, people whispered that her own mother Elizabeth was having an affair with Henry, too—and that her father Thomas Boleyn knew. But Henry, as always, had an answer for everything.
Just before his marriage to Anne, someone dared to ask Henry about his preference for Boleyn women. He replied: “Never with the mother.” While he may have let Elizabeth off the hook, with this revelation, he essentially verified his affair with Mary. We all know how messy Henry’s love life was—but what about a forgotten turn-of-the-century courtesan who was just as dramatic?
64. La Belle Otero: The Spanish Siren
In the late 19th century, there was one thing that princes, kings, kaisers, and tsars all had in common—La Belle Otero. For three decades, this legendary courtesan entranced the most powerful men in the world. She was so irresistible that men dueled over her, and it’s rumored that multiple men took their lives after she ended affairs with them. However, her life was also marked by bitter tragedy.
Forget Moulin Rouge or Memoirs of a Geisha—La Belle Otero’s story is even more heartbreaking, and a hundred times more twisted.
65. He Robbed Her Of Her Innocence
La Belle Otero was just a child—only 11 years old—when a horrific event altered the course of her life. While walking towards the fields near the village, the local shoemaker pounced on the little girl. He then dragged Otero, helpless and terrified, into the woods, threw her to the ground, assaulted her, and violated her.
Afterward, the shoemaker fled, leaving La Belle Otero to her fate. Even at such a young age, however, Otero was determined to survive. Within a year, she left her village and struck out on her own.
66. She Made A Name For Herself
La Belle Otero used her looks, grace, and charm to become a hugely successful singer and dancer—but that still wasn’t enough to pay the bills, so she turned to, ahem, entertaining powerful and wealthy men. It wasn’t long before some of the most powerful men in Europe took notice, including the Prince of Monaco and the Prince of Montenegro. But still, that wasn’t enough for her.
Next, she set her sights on one of Europe’s most infamous playboys.
67. She Moved Up In The World
Knowing the time and the place (Victorian England), could you take a guess as to who I mean? That’s right, La Belle Otero joined the ranks of other entries on this list like Lillie Langtry and Alice Keppel and took up with Edward VII AKA Dirty Bertie AKA the Playboy Prince. But there was just one problem—Lillie was still very much in the picture, and very, very jealous.
68. They Almost Got Caught
Like La Belle Otero, Lillie Langtry was in show biz. But that just meant that Bertie could have Otero on his arm whenever Langtry was off performing somewhere. However, it was an affair with an expiry date. After a seriously close call in Bertie’s customary private room at the restaurant he usually took Langtry to, he slipped out of La Belle Otero’s life. She took it in stride, though—he wasn’t the only one she had her eyes on.
69. Royalty Kept Her Going
Even when she had one powerful suitor, La Belle Otero had her eyes on the next rung up on the ladder. Take, for example, her affair with Russia’s Grand Duke Nikolai Nikolaevich. And, reportedly, his brother, Grand Duke Peter. They were great catches, but they were the tsar. If you can believe it, she actually had the gall to ask Nikolai for an introduction to Tsar Nicholas II. And, if you can believe it, it worked.
70. He Freaked Her Out
La Belle Otero had an affair with the last tsar, and he showed her the great theaters of Russia. She seemed genuinely fond of him, despite what she described as his timid, frightened nature and rank body odor. The one caveat? La Belle Otero said his tastes in the bedroom were so unusual that even she was surprised by them, although she declined to go into detail about what exactly those entailed.
However, much like Nicholas’s life, it was an affair with an expiry date.
71. She Got Sucked In
Men weren’t La Belle Otero’s only vice. She also, at one point, got way too into gambling, and lost tons of money in the process. Luckily, she always had exes to fall back on. No one was happier to save her than Prince Albert of Monaco—but the consequences of his very public affection for her probably caused more trouble for Otero than it was worth.
72. They Needed Her
On November 10, 1898, Prince Albert made the shocking decision to take La Belle Otero to Monaco with him. She knew this was a mistake, but had little choice. When she stepped foot into Monaco, her worst fears came true. Prince Albert’s wife had local authorities escort Otero to the border, and kicked her out of the country. Ouch. Well, joke’s on the wife.
By 1899, Monaco invited La Belle Otero back to their casinos; you see, Otero literally spent so much money gambling that her banishment put a dent in Monaco’s economy. Ha! Sadly, her good luck couldn’t last forever.
73. She Spent Everything She Had
From her retirement to her last days, La Belle Otero spent nearly all her money at the casinos. With only a couple hundred francs to her name, Otero lived out the rest of her life in increasing states of poverty, but still managed to eke out a relatively normal life. When the end came for her, it was April 10, 1965. La Belle Otero lived to the ripe old age of 97 years old—nearly a century.
There’s no doubt that during that time, she easily packed in enough scandal, action, and heartbreak for five centuries or more. La Belle Otero lived resplendently in her final years—but the same can’t be said for the Countess of Castiglione.
74. The Countess Of Castiglione: The Beauty With A Cruel Side
Virginia Oldoini—known better to history as the Countess of Castiglione—was mad, bad, and dangerous to know. The Italian aristocrat’s legendary beauty and photographic misadventures turned her into the world’s first model, but that’s not what made her INfamous. From her bedroom exploits to her tragic downfall, the Countess of Castiglione is one historical figure worth knowing.
75. Her Beauty Was Legendary
Growing up, it was clear to everyone who knew the girl that the young Oldoini was going to be a mega babe. She had long, wavy blonde hair, a refined face, and a legendary figure. By the time she was a teen, men were regularly trying to bed the beauty. Creepily enough, her parents were totally fine with this—in fact, they took advantage of it in the worst way possible.
76. She Was A Child Bride
When Virginia was just 17 years old, her parents wasted no time in marrying her off to Francesco Verasis, the Count of Castiglione. The count was 12 years older than the girl, and not much of a looker. There was one, and just exactly one, bright spot in Virginia’s marriage to her fuddy-duddy count: Their son together, Giorgio.
Oldoini doted on the boy as only a rich mommy can, pouring all her own frustrated hopes and dreams into him. Giorgio, in turn, adored her. Which makes the countess’ infamous act of revenge all the more savage.
77. She Was Well-Connected
Virginia had friends in high places, including her cousin, Camillo Benso. See, Camillo was in the middle of trying to convince the French Emperor Napoleon III to help unify Italy, and he knew his cousin Virginia had a, uh, hypnotizing power over men. He asked the countess to go to France and convince Napoleon to join their side. Yep, he wanted Oldoini to become a spy…but that wasn’t all.
The “convincing” Camillo had in mind wasn’t the kind that involves long debates. In fact, he specifically told the countess to “succeed by whatever means you wish—but succeed.” In other words: Bed that boy, and fast. So now Oldoini wasn’t just a spy, she was a honeypot.
78. She Knew Men’s Weak Spots
The Oldoini cousins couldn’t have picked a better mark than Napoleon III. A notorious womanizer, Napoleon also “suffered” from a chaste and pious wife, Empress Eugenie, who had long since stopped sleeping with her husband because she found him and his extra-marital escapades “disgusting.” Well enter: The Countess of Castiglione.
There was just one problem—she had to drag her middle-aged husband along with her. Well, she got a measure of revenge on him…
79. She Took Her Husband’s Money
Although infidelity is certainly close to #1 on the list of marital sins, the Countess of Castiglione didn’t stop there. Aside from taking up with Napoleon III in full view of her husband Francesco, the countess also literally bankrupted the man with her expensive tastes. Hey, you think a face that beautiful comes for free? Francesco wasn’t the only one she teed off, either.
Oldoini also loved to taunt Napoleon’s wife Eugenie and parade in front of her in expensive—and occasionally, see-through—clothing to flaunt her, ahem, assets. Did we mention Virginia was incredibly vain? Maybe a little too vain…
80. She Lost Her Lovers
Some courtiers, upon becoming acquainted with the Countess, made a surprising realization: She could be super boring. Her vanity turned people off—including her husband, who demanded a separation. He wasn’t the only one who tired of her antics, either. In the end, Oldoini’s illicit dalliance with Napoleon III was as short-lived as it was scandalous.
By 1860, their affair had soured, and the countess had completely lost favor at court. The reasons for her sudden fall from grace remain a private mystery—but her story doesn’t end there.
81. She Had a Disturbing Reaction to Aging
Oldoini did not cope well with aging, and her insecurities soon took on deranged proportions. Unable to confront her fading looks, the middle-aged countess insisted on spending her final years in black-colored rooms with closed blinds and no mirrors. Not even she was entitled to look at the waning beauty of the Countess of Castiglione. But that wasn’t her only sinister move…
82. Her Husband Tried to Punish Her
Sometime during her separation proceedings, the Countess of Castiglione’s estranged husband decided to ramp up the bitterness and do something truly horrific. He tried to claim custody of their only son Giorgio, using his wife’s lavish lifestyle as proof of her bad mothering. The countess’s response was swift and brutal.
83. She Gave a Cruel Payback
When Francesco tried to claim custody of her only beloved son Giorgio, the Countess of Castiglione didn’t take it lying down. Instead, she sent her ex a “present” in the mail. When he opened it, he was horrified. It was a seemingly innocent photograph of the beautiful countess dressed up in a luxurious gown—but when the count looked closer, his blood ran cold.
84. She Threatened Her Ex
Oldoini’s photograph was a warning shot to her estranged husband: In the portrait, the well-dressed countess was also holding a knife in her hand, half-hidden in the folds of her dress. The best part? She titled the photo “La Venegance,” just to make her message extra clear. Wouldn’t you know, she got custody of Giorgio for the rest of his life.
85. She Suffered an Unimaginable Tragedy
The Countess of Castiglione’s self-seclusion later in her life was rooted not just in vanity but also in tragedy. In 1879, little Giorgio passed from smallpox, predeceasing his utterly bereft mother by a cruel 20 years. Suddenly, her regime of funereal black rooms, veils, and never leaving the house makes tragic sense.
If you want to talk dramatic mourning, though, we’d be remiss not to include one of Edward VII’s most infamous mistresses…
86. Alice Keppel: The Last Royal Mistress
People like to see the Victorian age as prim, proper, and buttoned-up, but Alice Keppel proves them all wrong. The uncrowned queen of the “naughty nineties,” Keppel was one of the most scandalous women of her day—and most of her exploits went on behind tightly closed bedroom doors. Alice was a legendary beauty from the start, and her parents took advantage of this by marrying her off at a young age.
But there was one thing they couldn’t predict: her expensive tastes nearly immediately endangering her whole lifestyle.
87. She Found Support Elsewhere
Alice wasn’t about to stop spending and living it up just because her husband couldn’t afford it. The new Mrs. Keppel had a very bizarre solution to her financial problems. She decided to target wealthy men and strike up extramarital affairs with them, essentially using her renowned beauty and discretion to become a Victorian sugar baby. And it worked…a little too well.
88. A Prince Fell In Love With Her
In 1898, Alice Keppel met her destiny. The 29-year-old socialite was living in the affluent neighborhood of Mayfair in London and putting on pitch-perfect soirées as a hostess when she chanced to meet none other than Prince Edward, the eldest son of Queen Victoria and the heir to the English throne. I’d say it was the start of a beautiful friendship, but it was more like an outrageous romance.
89. Her New Lover Was Controversial
By this time, the Prince of Wales had quite the reputation for scandal. Although married to Alexandra of Denmark, he had scores of trysts with beautiful actresses and noblewomen throughout England. Historians believe he had at least 55 liaisons throughout his life, but that estimate is probably on the very low end. And that wasn’t all.
90. She Liked Bad Boys
Prince Edward couldn’t keep it in his pants, but he was so much more than your run-of-the-mill rake. He was notorious for his enormous appetites, both carnal and gastronomic, and earned the nickname “Dirty Bertie” for his debauched antics. As he got on in weight and age—the royal was 56 when he met Alice and old enough to be her father—Edward even famously commissioned a “love chair” that would let him romance a woman without crushing her with his considerable girth.
Yep, this is what Alice was getting herself into. Although, maybe it was Edward who should have watched out.
91. She Became An Uncrowned Queen
In 1901, Alice got a major life upgrade. That year, Queen Victoria passed, ending the Victorian age and ushering the Prince of Wales onto the throne as King Edward VII. The new Edwardian era had begun, and Keppel was right smack in the middle of the period. With Edward as monarch, the silver-tongued Keppel started acting as a go-between for her lover and his ministers. And believe me, she was powerful.
92. She Had One Failure
Keppel was one of the most persuasive women in all of England, and she could bend the ear of King Edward VII like nobody’s business. But she did have one fatal limit. No matter how hard she tried, Keppel could never convince the king to give up his material pleasures of cigars and eating, even while she tried to keep his appetites satisfied in the bedroom. This would have dire consequences.
93. Her Life Was About To Change
Once King Edward came back to dear Old Blighty in the spring of 1910, it all came completely undone. Before Keppel had the chance to properly reunite with her lover, Edward suffered several heart attacks in a row on May 6, 1910. But that wasn’t the worst part. Unable to admit any kind of defeat, the monarch refused to even lie down, saying, “No, I shall not give in; I shall go on; I shall work to the end.” It was Keppel who would live to regret it.
94. She Broke Down
When Alice got the news that King Edward was at the Grim Reaper’s door, the normally composed woman broke down, busting through the palace and indecorously running to be at his bedside. Although Alice’s old ally Queen Alexandra graciously let her in, the situation was pretty dang awkward, and the consort’s nerves were reasonably rattled about the whole situation. Well, they wouldn’t get any better.
95. Her Lover Committed A Huge Gaffe
With Edward surrounded by his family and his lover, he dropped a bombshell of a sentence. According to lore, the ailing king looked at his beloved Alice Keppel, then turned to Alexandra of Denmark and insisted she “kiss Alice,” as though this commandment would help smooth out the tensions in the room. Spoiler: It made things ten times worse.
At this point, even the forbearing Queen Alexandra couldn’t take it any longer, and she turned to Alice and asked her to leave the room. Keppel’s response has gone down in infamy.
96. She Caused An Infamous Scene
When Keppel realized the Queen of England had given her a direct command and that she would never see King Edward alive again, she took the situation from awkward to horrific. Once more, Keppel’s famous composure failed her, and she broke down into ragged sobs, screaming, “I never did any harm, there was nothing wrong between us! What is to become of me?” Sadly, it didn’t end there.
97. She Disgraced Herself
Keppel was so beside herself and nearly out of her mind that she couldn’t even leave the King’s bedside of her own free will. Eventually, more stoic members of the royal household had to drag the fallen mistress out, still sobbing and screaming, and all but threw her out into the street. Just after 11:30 in the evening on May 6, 1910, King Edward VII breathed his last, passing at the age of 68.
The King’s death wasn’t just the end of the Edwardian era; it was also the end of Alice Keppel’s ascendancy in the royal court. It wasn’t Keppel’s proudest moment—and boy, did she know it. When Keppel realized what an embarrassment she’d made of herself, she tried to bury it by…pretending it never happened.
98. She Gave An Embarrassing Goodbye
When the palace laid King Edward to rest on May 17, the now Dowager Queen Alexandra again allowed Alice Keppel to attend. But there was a disgraceful catch. In an obvious gesture to her illicit relationship with the king, the royal family forced Keppel to enter and leave through a side door. Ouch. For all that must have hurt, though, more pain was on the way.
Keppel had spent practically all her tenure as a royal mistress trying not to offend people, but try as she might, her innately scandalous position made her enormous enemies—including the new king, George V. Her time in the palace was capital-O Over. And really, that wasn’t the only era that ended that day…
99. She Has A Naughty Legacy
Yes, Alice Keppel turned into a relic of her saucy self by the end of her life, but her scorching legacy still continues today. Why? Well, her great-great-granddaughter is Camilla, the Duchess of Cornwall, the infamous mistress-turned-wife of Prince Charles—who just so happens to be King Edward VII’s great-great-great-grandson. This naughty fact wasn’t lost on Camilla, either.
When she first met Charles, legend has it Camilla quipped, “My great-great-grandmother was your great-great-grandfather’s mistress, so how about it?”
100. She Was The Last Royal Mistress
Keppel was something special—sure, she was super gorgeous, but I mean that in another way. Many historians consider her one of the last true royal mistresses, if not the last, for her outsized influence at court and her acceptance by the Firm itself. No mistress after her really held the same kind of power over a crowned king. They just don’t make ’em like Alice anymore.