Head-Rolling Facts About Henry VIII, England’s Murderous King

There are bad kings, there are horrible kings…and then there’s Henry VIII. Famous for his many wives and their various chilling ends, Henry nearly tore England apart in his quest for a son. He executed more people than any other English monarch in history, made his own church on a whim, and eventually betrayed basically anyone who had ever helped him. No, “horrible” doesn’t even begin to describe Henry. If you want to learn all the dirty details about this ruthless king’s rise to power, his reign of terror, and his gruesome end, dive in and discover Henry VIII’s twisted history.


1. His Father Was A Warrior

Henry VIII was born on June 28, 1491, with big shoes to fill. His father was the triumphant Henry VII, who had won the Wars of the Roses, and his maternal grandfather was the fearsome King Edward IV. However, despite how his life turned out, Henry wasn’t supposed to step into those shoes. In fact, as far as royals go, Henry was kind of a nobody at first.

2. He Wasn’t Going To Be King

See, Henry was his parents’ third child and second son. His sister, Margaret Tudor, was the eldest, and his brother Arthur was the heir to the throne. As the next king, Big Artie got all of his parents’ attention, and Henry was mostly forgotten. But, the Tudors had a way of dropping like flies—something Henry’s parents would learn all too soon.

3. His Childhood Was Mysterious

Since Henry wasn’t supposed to become king, no one really cared much about him when he was young. No writers, at least. We have almost no record of what he was up to during his childhood because no one bothered to write any of it down. One of the few things we know is that he played a pretty noticeable role at the wedding of his brother Arthur and Catherine of Aragon.

He was probably mostly there to look cute and support his brother. I doubt anyone realized that Catherine would be marrying that cute little boy soon enough.

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4. He Lost His Brother As A Boy

Less than a year after Arthur and Catherine tied the knot, tragedy suddenly struck. In what seemed like the blink of an eye, the strapping, 15-year-old Arthur went from healthy to dead. Out of nowhere, Henry, the forgotten prince, was now the heir to the throne of England. Pretty quickly, people around the court started to realize that was not a good thing.

5. He Barely Knew His Father

Henry VII was a good warrior and a capable king, but his fatherly instincts left a lot to be desired. He was far more concerned with running his country than with preparing his boy to do the same. Even though Henry VIII was now the heir, he still had basically nothing to do. He almost never appeared in public, and received very little training in how to be a good king.

That makes sense, because he would end up being maybe the worst king in the entire history of England.

6. He Was A Lazy Teenager

If you had known Henry back then, you probably wouldn’t have thought he’d make a good king. He liked to sleep in, he hated work and school, and he only ever wanted to go hunting or hawking. Even in his youth, he spent his nights gambling, drinking, dancing, and playing cards. Maybe people hoped that when he became king, he’d finally learn some responsibility. If anything, he only got worse.

7. He Married His Brother’s Widow

On April 21, 1509, the day everyone had been dreading arrived. Henry Tudor succumbed to tuberculosis, and his son succeeded him. The 17-year-old Prince Henry became King Henry VIII. Awkwardly, one of his first acts was to marry his brother’s widow, Catherine of Aragon. It’s fitting that the first thing he did as king was get married—because the twisted history of Henry VIII’s many wives would be the thing he’d eventually become the most infamous for.

8. He Got Chopping Immediately

Actually, we’re getting ahead of ourselves. Marrying Catherine of Aragon wasn’t the first thing Henry did as king. Two days after his coronation, he had two of his father’s ministers thrown in the Tower of London, charged with high treason, and beheaded. Henry learned very quickly that the executioner was an easy way to solve his problems—and a lot more people would get the chop in the years to come.

9. He Was Utterly Sadistic

Henry VIII came to love executing people. He loved it so much that he had to invent new and exciting ways to do it. One of his favorites was called “pressing.” It involved putting a prisoner under a massive slab of wood and slowly adding weights until they were crushed alive. Henry made sure to add the weights as slowly he could, to make the whole thing as agonizing as possible.

It turns out, the new king could be incredibly cruel—something his many wives had to learn the hard way.

10. He Lost His First Child

Immediately after their wedding, Henry and Catherine conceived a child. The couple was ecstatic, but nine months later, grief replaced their joy. The child was stillborn. They were inconsolable, but this was just a dark omen of things to come. A few months after the miscarriage, Catherine became pregnant again. This time, she gave birth to a boy. Gracefully, this child survived—but even worse heartbreak was on the horizon.

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11. His Woes Were Only Beginning

Henry and Catherine’s first son, Henry, passed seven weeks after his birth. Next came two more stillbirths. A dark cloud started growing over the royal household, and Henry and Catherine’s relationship grew more and more strained. Not even the birth of a healthy child, Mary, in 1516 could save them now. Henry blamed Catherine for his lack of an heir—and it would drive him to dark places.

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12. He Slept Around

It didn’t take long for Henry to start taking mistresses. He bedded all kinds of wealthy and important women, but his most infamous mistress was a complete nobody. Bessie Blount was the daughter of a small-time politician, but she caught the king’s eye and the rest was history. Sure, Blount wasn’t particularly rich or powerful, but she gave Henry something that none of his other mistresses—or his wife, for that matter—could.

13. He Had A Son—But Not With His Wife

In 1519, Bessie Blount gave birth to Henry’s son. She named him after his father, and young Henry FitzRoy became a scandal at the English Court. Most times, if a king gave birth to an illegitimate child, they would never admit it. But not Henry. In a move that shocked the country, Henry proudly acknowledged the boy as his own. People were baffled—but Henry had his reasons…

14. He Was Insecure About His Manhood

Before Henry FitzRoy came around, people were starting to talk about the king. He’d been married for a decade and still had no male heir. In medieval thinking, maybe that meant there was something wrong with Henry’s manhood. In his mind, this illegitimate son was proof that he was a real man, and that his lack of an heir was entirely his wife’s fault.

But even if the boy made Henry feel better, little Henry FitzRoy did nothing to solve Henry’s marital problems—and the king was starting to get desperate.

15. He Wanted An Heir—And Bad

At this point, the English court was completely absorbed with what became known as “The King’s Great Matter:” Henry’s lack of a son. The way he saw it, he had three options: Somehow legitimize Henry FitzRoy, marry his daughter Mary off ASAP and pray for a grandson, or blame it all on Catherine, ditch her, and find someone new.

The third option was probably the most complicated and definitely the cruelest—but it involved Henry getting a hot, young, new wife. Which do you think he chose?

16. He Liked Sisters

So how did Henry pick his future wife? Easy. He was already sleeping with the beautiful Mary Boleyn—most people assumed that Henry was the real father to Mary’s two young children—so Henry made the obvious choice: Mary’s younger sister, Anne! But, he would soon learn, Anne Boleyn was no easy target…

17. He Picked A Heck Of A Woman

By 1525, Henry was completely fed up with Catherine and falling head over heels for Anne Boleyn. However, he didn’t count on one thing: Anne wasn’t into it. At all. Anne was young, intelligent, charismatic, and entirely uninterested in becoming yet another of Henry’s floozies. She resisted for as long as she could—but this is Henry VIII we’re talking about. He almost always ended up getting what he wanted—and Anne was no exception.

18. He Was A Babe

Henry VIII was undoubtedly an absolutely brutal man, but keep in mind: He was actually pretty hot. Despite the rotund portraits from his later life, Henry was actually a complete stud in his youth. He was tall, athletic, and incredibly charismatic. Women tended to love him—until he turned on them, at least. So while Anne Boleyn resisted at first, soon enough she fell right into Henry’s arms.

She didn’t know it yet, but she’d made a terrible mistake.

19. He Decided To Abandon His Wife

Henry finally came up with a solution to “The King’s Great Matter.” He chose the cruelest, riskiest, and most complicated option: He was going to leave Catherine of Aragon and marry Anne Boleyn. It sounds like a pretty simple matter, but in the 16th century, it was anything but. Henry’s blind desire would end up tearing his country apart.

20. He Disobeyed The Church

Henry really wanted to leave Catherine, but there was just one problem: The Church. See, the pope wasn’t too keen on the idea of divorce. Henry tried to convince Pope Clement VII that their marriage was invalid to begin with, but the pontiff wasn’t buying it. If the king was going to get a divorce, he was going to do it without the Church’s permission.

And that’s just what Henry did. He was going to make Anne Boleyn his wife, no matter the cost—and the cost was incalculable.

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21. So He Made His Own Church

All because he thought marrying Anne Boleyn would give him a son, Henry VIII set off the English Reformation. This massive schism would set off a vicious religious conflict that continued for centuries, but Henry didn’t care. He got what he wanted, and that was that.

22. He Abandoned His Religion

Weirdly enough, Henry had spent his life to this point as an incredibly devout Catholic. He’d done a lot for the Church, and they loved him for it—but nothing was going to stop him from getting what he wanted. When it came time to choose between the Church and a new wife, Henry didn’t hesitate.

23. He Kicked His Wife Out

Henry and Catherine had been married for 24 years, but in the end, not one second of it mattered to Henry. Before their divorce was even official (if you can even call it that), he unceremoniously banished her from the court and gave her rooms to Anne Boleyn. The king rejoiced, convinced that his problems were finally over—but in reality, he had only taken the first step down an incredibly twisted path.

24. He Was Technically A Bigamist

Henry actually married Anne Boleyn and knocked her up before his split from Catherine of Aragon was official. He’d spent a quarter of a century waiting for a son, and he was done wasting time. Finally, several months after his wedding to Anne Boleyn, Henry had his marriage to Catherine declared null and void. Basically, Henry claimed that since Catherine had married his brother (for five months), their marriage was “unnatural.”

Was it a good reason? No. Did Henry care? Not one bit.

25. He Wanted To Send A Message

If this whole affair seems pretty darn shady to you, you’re not the only one. In 1532, Elizabeth Barton, a Catholic nun known as “The Nun of Kent” and “The Holy Maid of London,” began prophesying that Henry’s marriage to Anne Boleyn would result in his brutal downfall. She said what many were thinking—and she paid a horrific price for it.

In 1533, authorities apprehended her and forced her to admit that she’d made everything up. Henry quickly had her executed for treason. He then had his men place her head on a spike on London Bridge; the only woman to ever receive that “honor.”

26. His Problems Were Far From Solved

Less than nine months after their “official” marriage, Henry and Anne welcomed…a daughter. Henry named her Elizabeth after his mother, Elizabeth of York, but he couldn’t hide his disappointment. After all that work to finally get a son, he was stuck with yet another daughter. What he didn’t realize is that this unwanted daughter would go on to become ten times the monarch he’d ever be.

But for the time being, Henry couldn’t pout too much—he suddenly had much bigger problems to deal with.

27. He Made An Enemy Of The Church

Maybe if Henry had just ignored the Pope, divorced Catherine, married Anne, and left it at that, things would have been awkward for a bit, then ended up fine. But that’s not what Henry did—he took it so much further. First, he formed the Church of England and put himself in charge. Then, he signed the Act in Restraint of Appeals, which essentially said that Rome had zero say in English religious matters.

The pope could no longer ignore what Henry was doing. He officially excommunicated Henry, and the break between the Catholic Church and the Church of England was complete. Oh well, at least his new marriage was going great, right? Well, about that…

28. He Started Having Second Thoughts

Henry VIII found the gorgeous Anne Boleyn irresistible…when he couldn’t have her. Turns out, married life was a different story. Anne was stubborn, independent, and had a temper—a far cry from the demure, submissive trophy wife he wanted. And if things got off to a rocky start, they only got worse from there.

29. He Blamed His New Wife

The birth of Princess Elizabeth was a huge disappointment for Henry. Anne got pregnant again soon after—but if Elizabeth was disappointing, this next pregnancy was a disaster. Anne had a miscarriage in 1534, and Henry was not pleased. He’d left his wife of 24 years just so Anne could give him a son, and now she couldn’t even do that! Was it her fault? Of course not, but there was no telling Henry that.

Anne’s miscarriage cast a shadow over the entire English court—but dark rumors suggested things were even more messed-up than they seemed.

30. Anne Might Have Had A Secret

Anne Boleyn wasn’t exactly happy with her marriage, but she was smart enough to know that angering Henry wasn’t in her best interest. She was desperate to give him a son—and some people believe she was willing to do anything to make it happen. Many in England didn’t believe that Anne had had a miscarriage at all. Rather, they claimed she lied about the whole pregnancy.

And, if Anne’s baby problems weren’t enough, her sister was still out there making things a whole lot more difficult.

31. His Old Mistress Embarrassed Him

Mary Boleyn didn’t just disappear after Henry cast her aside. Awkward as it may have been, she was still the Queen’s sister and an important part of the royal household. But Mary played by her own rules, to the fury of both Henry and her sister. She was difficult at the best of times—but when the king and queen discovered the secret she’d been hiding from them, they had finally had enough.

Mary Boleyn had fallen in love with a lowborn soldier and secretly married him. This erased any chance of Henry using her in a political match. Both he and Anne were livid, and they made Mary pay for it.

32. He Nearly Erased Her From History

If there’s a reason most people don’t know much about Mary Boleyn, it’s probably because of her dark end. When Henry and Anne found out that Mary had married a commoner, they banished her from court forever. Mary went from a life of luxury to utter obscurity overnight. She never saw her sister again, and she passed a few years later, completely forgotten.

33. He Kept Sleeping Around

How did Henry VIII cope with his miserable marriage to Anne Boleyn? The same way he’d coped with his miserable marriage to Catherine of Aragon: Mistresses. As his union with Anne started falling apart, he fell into the arms of a minor lady named Madge Shelton. However, some historians differ and claim it was Madge’s sister Mary. Maybe it was both—we know that Henry had a thing for sisters…

34. He Kept On Chopping Off Heads

As if Henry didn’t have enough on his hands with his disaster of a second marriage, he still had that whole religious revolution thing to deal with. Turns out, when you force an entire country to change religions on a whim, not everyone will be very happy about it. Countless religious figures openly rebelled against Henry’s new Church of England—but Henry had learned how to deal with his critics very early on in his reign.

Within just a couple of years of the schism, Henry had summarily executed dozens of prominent monks and Bishops for “treason” and “heresy.” And once he got the heads rolling, he just couldn’t stop.

35. An Accident Made Everything Go Wrong

The tension in Henry VIII’s court came to a boiling point around the New Year in 1536. Anne Boleyn was pregnant yet again, totally aware that if the child was not a son, her days were numbered. Things were tense enough as it is, then one day, news of a terrible accident reached the palace. During a jousting tournament, a rival had knocked Henry off his horse, leaving him horribly injured.

That accident would change Henry forever. If he’d been cruel before, he was about to take things to a whole new level.

36. He Lost Another Son

When Anne heard about Henry’s accident, it shocked her so much that she suffered another miscarriage. And, to put salt in the wound, doctors revealed that the child had been a boy who potentially could have ended the Queen’s woes. In a strange twist of fate, the miscarriage happened on the exact same day that Catherine of Aragon, Henry’s forgotten first wife, passed of a mysterious illness.

Not only did Anne mourn the loss of her child, she knew that she probably wouldn’t get another chance. Still, no one expected Henry’s response to be as disturbing as it was.

37. He Let His New Mistress Move In

Even though his wife recovered from her miscarriage, Henry was clearly done with her. First, he began refusing to grant political offices to her family. Then, in an unprecedented move, he moved his latest mistress, the 28-year-old Jane Seymour, into swanky new rooms in his palace. It was basically a slap in the face for Anne—but if that had been the end of it, she should have considered herself lucky.

38. He Accused His Wife

Henry finally did what his wife so feared in the spring of 1536. He had Anne, her brother, and four other men thrown in the Tower of London. The courts accused each of the men (including her own brother) of sleeping with the queen, an act of treason. Henry accused Anne of adultery as well, along with incest and witchcraft for good measure.

39. He Beheaded His Own Queen

There was essentially no evidence for any of these accusations, but since when had Henry ever needed evidence? The headsman claimed the five men on May 17, 1536, and Anne followed suit two days later. A crowd gathered to watch this never-before-seen spectacle: The Queen of England herself, beheaded like an animal.

Henry barely waited until her head had stopped rolling before he was already onto the next one.

40. He Moved On Quick

In a move that surprised no one, the 45-year-old Henry VIII became engaged to the almost 20-years-younger Jane Seymour the day after Anne Boleyn’s execution. Their marriage took place 10 days later. For any other king, this would have been a scandal beyond measure—but for Henry, this was pretty much just business as usual.

So, after two catastrophic marriages, this would finally be the one that would work out, right? What do you think…

41. He Finally Had A Son

Henry VIII’s marriage to Jane Seymour got off to the best possible start. On October 12, 1537, Seymour gave birth to a…wait for it…boy! The entire nation breathed a sigh of relief as Prince Edward finally meant an end to the chaos that had lasted nearly a decade at this point. But it took less than two weeks for tragedy to strike, throwing Henry’s court into upheaval once again.

42. But He Paid A Terrible Price

Jane Seymour had access to the best doctors in England—but unfortunately, the best doctors in 1537 weren’t worth that much. Edward’s birth was agonizing, and the queen suffered a terrible infection. The doctors proved helpless, and Henry had to watch as his beloved wife—the first to give him a healthy son—withered away.

Jane Seymour succumbed to her infection on October 24. Unfortunately, that meant yet another poor woman would end up calling Henry VIII her husband.

43. Not That He Cared

Jane Seymour passed from this life with her head still intact, but don’t go thinking that Henry actually cared for her. During her agonizing labor, doctors told the king that it may come down to saving either the child or the queen. Henry’s reply was utterly heartless: “If you cannot save both, at least let the child live,” he said. Twisting the knife in, he then added, “For other wives are easily found.”

Henry got what he wanted, and the child lived instead of the mother—but karma would come for him soon enough.

44. He Grew Darker By The Day

Jane Seymour’s demise marked a change in Henry VIII. A divorce, an execution, and a fatal childbirth had finally made their mark on him. He began growing morbidly obese and started suffering from diabetes and gout. His mood somehow grew even darker, and he became paranoid and irrational. He’d never been a ray of sunshine, but this is the point where Henry became truly deranged.

45. He Had A Really Craft Ally

There weren’t many people left whom Henry trusted, but one of them was his shifty spymaster, Thomas Cromwell. Cromwell had been scheming behind the scenes all this time, engineering the biggest moments of Henry’s reign. He arranged the annulment of Henry’s marriage to Catherine of Aragon, he masterminded the Reformation, and he helped poison Henry’s mind against Anne Boleyn.

Cromwell was as ambitious as he was ruthless—and he was maybe the worst person to have around when Henry took a turn for the worse.

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46. He Became Paranoid

As Henry VIII was growing fat, ill, and paranoid, Thomas Cromwell was right next to him, whispering into his ear and fueling the king’s suspicions. Henry started perceiving threats to his crown around every corner—and this was a guy who executed people at the drop of a hat at the best of times. England became a terrifying place to be.

Maybe the nation hoped if the king found a new wife he would go back to his regular amount of crazy. Nope.

47. His Advisor Made A Horrible Mistake

Thomas Cromwell was one of the most powerful men in England—until he suggested Henry marry the 25-year-old German Duchess Anne of Cleves. It seemed like a perfect match, and Anne’s father could prove a vital ally if a religious war happened to break out. There was only problem: Political marriages were all well and good, but Henry wasn’t about to marry someone he’d never even seen! What if she was ugly?! But don’t worry, Cromwell had the perfect solution…

48. He Agreed To A Marriage Without Meeting Her

If a picture’s worth a thousand words, a portrait’s gotta be worth, I don’t know, at least 300? Henry sent one of the best portrait artists in the world to paint Anne so he could judge her for himself. When the painting finally made it back to him—along with Thomas Cromwell’s assurances that Anne was basically his dream gal—Henry was finally convinced.

Little did he know, he was in for a rude awakening.

49. He Regretted The Decision Instantly

Reportedly, when they finally met, Henry VIII took one look at Anne of Cleves and realized he’d made a horrible mistake. Whether it was her looks or her personality, Henry was already looking for an exit before they’d even tied the knot. They lasted a whopping six months, and if we’re to believe Henry’s word, they didn’t even consummate the union.

The whole affair left a sour taste in Henry’s mouth—and he was looking for someone to blame. Maybe the guy who suggested Anne in the first place?

50. He Made His Wife His Sister

In one of the most awkward titles in history, after Henry annulled his marriage to Anne of Cleves, he dubbed her “The King’s Sister.” As far as consolation prizes go, that’s about as bad as they get. But don’t worry—in the end, Anne would end up getting the last laugh. She was one of the rare wives who actually managed to outlive Henry VIII.

51. His Next Wife Was The Youngest Yet

Whatever it was, Anne of Cleves just didn’t do it for the now-46-year-old Henry. But you know who did? The 17-year-old Catherine Howard. Apparently, Henry realized that political marriages weren’t for him and went back to marrying whoever he had the hots for. But not everyone was happy about this latest match.

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52. His Advisor Made One Too Many Mistakes

Thomas Cromwell made the Anne of Cleves match happen, only to watch as it went up in flames almost immediately. Then, to make things worse, Henry started chasing Catherine Howard. What’s so bad about that? Howard happened to be the Duke of Norfolk’s niece, and the Duke of Norfolk happened to be one of Cromwell’s biggest political rivals.

Suddenly, Cromwell started to feel the walls closing in around him—but he didn’t yet realize how bad things had gotten.

53. He Sent Cromwell A Message

First, Henry ditched the wife Cromwell chose for him. Next, he started eyeing a girl related to one of Cromwell’s biggest enemies. If Cromwell didn’t see the writing on the wall, Henry’s next chilling act certainly made it clear: Henry had three of Cromwell’s cronies burned at the stake for heresy. No one knows exactly why Henry turned on his biggest ally so abruptly—but this is the insane Henry VIII we’re talking about, did he really need a reason?

When he finally betrayed Thomas Cromwell for good, it was absolutely brutal.

54. He Betrayed His Closest Ally

Thomas Cromwell spent his final days looking over his shoulder wherever he went. He’d made a lot of enemies during Henry’s reign of terror, and the tides had finally turned. The Duke of Norfolk and Cromwell’s other rivals finally convinced Henry that his one-time advisor had to go. The king, still sore about Anne of Cleves, didn’t take much convincing. Henry charged Cromwell with treason and a pile of other trumped-up accusations.

In the end, despite everything he’d done for Henry, Cromwell met the same fate as everyone else who got in the murderous king’s way: His head laying at an executioner’s feet.

55. He Got Two Birds With One Stone

Henry didn’t even bother to show up at his friend’s execution—he was busy getting married for the fifth time! He tied the knot with Catherine Howard the very same day. Not only was she less than half his age, she was also Anne Boleyn’s cousin and former lady in waiting. Awkward… The timing of the nuptials even allowed Henry to give his wife a particularly nice wedding gift: He gave his new queen all of Thomas Cromwell’s lands! Not like he using them anymore.

56. His Latest Wife Turned The Tables

Catherine Howard ended up meeting a similarly dark fate to Henry VIII’s other wives, but at least she gave him a taste of his own medicine. See, while Catherine hadn’t yet turned 20, she still managed to get around. She had several notorious affairs even before she married Henry, and putting a ring on it didn’t slow her down one bit.

But, as she would learn, crossing Henry VIII rarely ended well.

57. He Didn’t Believe His Wife Would Cheat

Almost as soon as she wed Henry, Catherine Howard began an affair with one of his courtiers, a man by the name of Thomas Culpeper. Since there are no secrets in a royal palace, news of the tryst soon got back to the king. This time though, it seems as though Henry was head-over-heels in a way he hadn’t been in years. He refused to believe the rumors and stood by his queen.

Soon enough though, a man from Catherine’s past would seal her fate for good.

58. He Couldn’t Deny The Truth

Before she was a queen, Catherine Howard had had an affair with another Tudor courtier, Francis Dereham. They’d actually been engaged at one point before Catherine caught the king’s eye. Strangely, Howard hired Dereham to work for her when she married Henry—and it turned out to be the last mistake she’d ever make.

Dereham confessed to having an affair with Catherine in the past—but even worse, he outed her relationship with Culpeper. Finally, Henry had to admit the truth: After years of cheating on his wives, this time, he was the one wearing the horns.

59. His Wife Tried To Save Herself

Give her credit, Catherine Howard didn’t go down without a fight. When officials questioned her about Dereham’s claims, she came back at him twice as hard. She claimed she never cared for him, and in fact that he’d forced her into an adulterous relationship against her will. We’ll never know the whole truth of what went on between them. All we know is what happened next.

Henry charged Catherine, Dereham, and Culpeper with treason, and sentenced them to beheading.

60. She Begged For Mercy

Allegedly, Catherine Howard did not take the news that she was going to lose her head well. The now-19-year-old queen allegedly broke free from her guards and ran through the halls, screaming for Henry to show her mercy. She never made it to him, however—in fact, she would never see the king again. According to legend, her ghost remains in those same halls to this day, and people have often claimed to have heard her screams for mercy in the infamous Haunted Gallery.

61. He Beheaded Yet Another Queen

No amount of screaming could save Catherine or her two lovers from their fate. On February 13, 1542, Henry had all three of them beheaded. That makes five wives down, two of them by Henry’s own hand. You’d think he’d finally call it quits at this point. After all, he had an heir, he was growing old, fat, and infirm, and fate didn’t seem to be on his side.

But when it came to women, Henry VIII couldn’t help himself. He just had to have one last go at it—and finally, this time, Henry would be the one who didn’t make it out of the marriage alive.

62. He Actually Did Some Stuff Other Than Get Married

It might be hard to believe at this point, but Henry was actually, you know, a king while all of this wife-swapping was going on. That means in between beheading innocent women, Henry also had a country to run. Surprisingly, Henry actually found time to be something of a capable military leader—which came in handy in 1542, when decades of tension finally boiled over into outright conflict with Scotland.

For once, Henry set his mind to something other than a woman, and sought to take Scotland for his own—but of course, with Henry VIII, things were never that easy.

63. He Wanted Scotland

After defeating the Scots at the Battle of Solway Moss, Henry tried to take the Scottish crown the easy way. He suggested a marriage between Mary, Queen of Scots, and his son Edward. Wouldn’t you know it, that would make Edward King of both England and Scotland. It would have put an end to the ceaseless fighting between England and Scotland—but the Scots weren’t going to give up that easy.

The Scottish Parliament rejected the marriage. In Henry’s mind, that meant they opted for “the hard way.” The two countries broke out into open war—and the fighting would go on for the rest of Henry’s life.

64. He Juggled Wars

Getting the Scottish crown would be nice, but it still wasn’t enough for a man of Henry’s appetite. While the conflict with Scotland raged on, Henry also decided to team up with Charles V, Holy Roman Emperor, and invade France. Remarkably, for a man of his age, size, and lack of experience with martial matters, Henry personally led his men to a remarkable victory at Boulogne.

Henry had won the single biggest victory of his entire life—but like with everything else in his life, he still managed to screw it up for himself.

65. He Actually Won Something

Henry and Charles had a falling out, which led to Charles making peace with France and abandoning the English king in enemy territory. The French tried to turn the tide and invade England while Henry was away, but the English forces turned them back. Finally, the French king had to concede defeat and sign the Treaty of Camp. This officially made Boulogne an English territory…for about a second.

66. It Was All For Nothing

As soon as the French gave Henry Boulogne, he sold it right back to him. See, turns out, wars are expensive, and even though Henry won, he went flat-broke doing it. In the end, the whole business, including who knows how many dead soldiers, ended up accomplishing basically nothing. Speaking of a bunch of deaths accomplishing basically nothing, let’s get back to Henry’s love life, because there’s still one more wife to go.

67. His Last Marriage Was The Least Dramatic

In July 1543, Heny VIII wed for the last time. His latest bride was Catherine Parr, and she couldn’t have been more different from Henry’s previous wives. First of all, she was almost age-appropriate, at 31 years old. She was also remarkably stable, compared to his previous wives. There were no wild cheating scandals or swirling rumors.

In fact, Catherine Parr managed to do something none of Henry’s other wives ever did: She made a somewhat decent man out of him.

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68. He Made Up With His Kids

Years earlier, as a way of sticking it to his various hated wives, Henry had cut his two daughters, Mary and Elizabeth, out of the line of succession. They spent the subsequent years in a tense limbo, unsure if their father would turn on them. Parr made Henry bury the hatchet with his two daughters, and he finally brought them back into the line of succession.

So basically, without Catherine Parr, England would have missed out on Queen Elizabeth, one of its greatest monarchs ever.

Henry VIII FactsWikipedia

69. He Became Grotesque In His Old Age

While the young Henry VIII had been quite the piece of meat, the old Henry VIII was a different story entirely. By this point, his waist had ballooned to 54 inches, and he could barely even walk. He needed attendants to wheel him around wherever he went. The weight was just the beginning of his problems, though: The worst part was the gout, which left him covered in excruciating, pus-filled boils.

Finally, Henry VIII looked as bad on the outside as he was on the inside.

70. His End Wasn’t Pretty

Anyone who knew Henry VIII near the end could tell that the grim reaper wouldn’t be long. He passed of an illness related to his obesity at age 55. With that, Catherine Parr and Anne of Cleves could at least claim they were the only wives to outlive the murderous king. In a surprising request, Henry asked his attendants to bury him right next to Jane Seymour, the only wife he didn’t abandon.

Goes to show, after all of his wives, there was only one thing Henry actually cared about: He wanted lay next to the one wife who gave him a son.

71. His Last Words Were Mysterious

Historians have no firm record of Henry’s final words, but rumors persisted that he cryptically cried “Monks! Monks! Monks!” before his final breath left him.

72. His First Son Almost Became A Prince

Ever wonder what happened to Henry FitzRoy, the illegitimate son who caused such a stir in Henry’s younger days? Turns out, he lived through more scandals than just his birth. Back before Henry had a legitimate heir, he strongly considered acknowledging FitzRoy. He wanted a male heir—and he was willing to go to utterly disturbing lengths to make sure it happened.

73. He Almost Married His Son And Daughter

Even though FitzRoy was born out of wedlock, Henry spoiled him rotten—something that infuriated his then-wife, Catherine of Aragon. This is when a cardinal suggesting a twisted solution to all of the couple’s problems: Marry FitzRoy to his half-sister, Henry and Catherine’s daughter Mary. This would strengthen FitzRoy’s claim to the throne, making Henry happy. It would also ensure Mary ended up on the throne herself, making Catherine happy.

In the end, they didn’t go through with it. Henry VIII did a lot of seriously messed up things, but thankfully, forcing his son and daughter to get married was not one of them.

74. He Cast Aside His Most Famous Mistress

Speaking of Henry FitzRoy, there’s also the sad fate of his mother, Bessie Blount. At one time, Blount was Henry’s most infamous mistress—and that made her an incredibly powerful woman. She had the king’s ear at a time when he listened to no one else. But, as much as Henry liked women, he grew tired of them incredibly quickly. Though he cared for her once, Blount’s fall from grace was total.

Henry unceremoniously tossed Blount aside when he was done with her, and she passed in utter obscurity. Her story has nearly been wiped from history, and even her burial place is unknown.

75. There Might Be More To Anne Of Cleves’ Story

Anne of Cleves is now infamous as Henry’s rejected queen, but was it really so simple as “Henry found her ugly and cast her aside?” Modern historians suggest a more disturbing reason for his disgust. Anne’s first meeting with Henry was a diplomatic blunder: Making their way to London, Anne’s party stopped on New Year’s Day 1540 at Rochester, where she took time to look at bull-baiting from the window. Suddenly, an old burly stranger entered the room—and everything went horribly wrong.

76. He Disguised Himself

You see, this stranger was really Henry VIII in disguise. He had wanted to creep in and get a sneak peek of his new bride-to-be. He also expected that she would see through his costume via the power of “true love”…or something. Spoiler: This was not a good idea. When he approached Anne, her response made his blood run cold.

77. She Shut Him Down

Depending on the account, either Henry tried to get Anne’s attention and she politely ignored him, or he outright tried to kiss and grope her, which understandably horrified the young woman. Either way, it was a disaster, and Henry left the encounter angry, embarrassed, and possibly ready to take revenge…

78. He Never Forgave Her

Some modern historians believe that this ill-fated early encounter between Anne of Cleves and Henry VIII sealed her fate. According to them, Anne’s lack of enthusiasm for Henry (even in disguise) made the king put up his defenses. If he didn’t impress her, he may have decided she didn’t impress him either, no matter what. And the rest, as they say, is history.

79. Even The Men Who Wiped His Butt Were Powerful

One of the most prestigious positions in Henry VIII’s court was as one of his “Grooms of the Stool.” These men attended to the king’s every whim, including wiping his royal butt after using the bathroom. It sounds awful, but being in such close proximity with the king made the Grooms of the stool remarkably powerful. However, such intimacy with the king was a double-edged sword.

When looking for scapegoats to accuse of adultery with Anne Boleyn, one of the king’s Grooms, Sir Henry Norris, got unlucky. Out of nowhere, Henry accused Norris and executed him for treason.

80. His First Wife Met A Gruesome End

Catherine of Aragon got out of her marriage to Henry VIII alive, but she didn’t last too long afterward. She passed just a few years later, and her demise was utterly mysterious in its time. While preparing her body for burial, her embalmer noticed the corpse looked in perfect health—save for her heart, which had turned black. The ghastly and seemingly fatal condition, coupled with Catherine’s premonitions of her own end, led people to some dark rumors about her end…

81. People Thought It Wasn’t An Accident

After witnessing her strange condition, those loyal to Catherine and disloyal to Henry and Anne Boleyn started whispering that the Royal Couple 2.0 had poisoned Catherine in a chilling act of self-service, leading the “Dowager” to die poetically of a broken heart. Modern historians, however, believe a much different story.

82. He Destroyed Her Heart

Most experts today believe that rather than foul play, Catherine passed of cancer of the heart; sometimes it can turn the heart black. If nothing else, that would be an incredibly poetic end for a wife of Henry VIII.

83. Catherine Howard’s Final Words Cut Deep

One of the most persistent legends about Henry VIII’s wives is the final words of Catherine Howard. According to popular folklore, her last words were, “I die a Queen, but I would rather have died the wife of Culpeper”. However, no eyewitness accounts support this, instead reporting that her last utterance was a whole lot more heartbreaking.

Instead of that defiant cry, Howard spent her final moments asking for forgiveness for her sins and acknowledging that she deserved to die “a thousand deaths” for betraying the king, who had always treated her so graciously.

84. Anne Boleyn Made A Final Plea At The End

At the end of the day, the most infamous of Henry’s spurned wives has to be Anne Boleyn—but her end was even worse than people realize. After four days in the Tower of London, Boleyn bundled up a package and gave it to her guard to deliver to the king. It was a letter, and her very last to Henry. In it, she plead for mercy, writing that “never prince had wife more loyal in all duty, and in all true affection, than you have ever found in Anne Boleyn.” She also made one final heartbreaking request.

85. She Begged For Mercy

In her final letter to King Henry, Boleyn begged him to think of their daughter Elizabeth, and then she humbly asked that Henry, if he went through with it, would still spare the lives of her brother and the other men accused of being her lovers. It’s a gut-wrenching revelation: At her core, until the very end, Boleyn was truly selfless. But it didn’t go her way. The men met the axe the same as her.

Unfortunately, she married Henry VIII, England’s murderous king. She never stood a chance.

Take a quiz to see what you learned.

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Catherine Howard FactsWikimedia Commons

Sources: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11

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