A portrait had convinced him. The woman in the painting was young, poised, and pleasing to the eye, and Henry VIII had made up his mind almost at once. She would be his fourth wife. Thomas Cromwell, his spymaster, had assured him she was a perfect match, and the match itself was a political masterstroke.

The Duke of Cleves, her father, could prove a vital ally if religious war broke out across Europe. Henry had only one condition: he refused to marry a woman he had never seen. What if she was ugly? Cromwell had a solution — he sent one of the finest portrait artists in the world to paint her, so the king could judge for himself.

When the painting arrived, accompanied by Cromwell’s assurances that Anne of Cleves was basically his dream woman, Henry was convinced. But the woman he met on the road was not the woman in the painting. When they finally came face to face, Henry took one look at his bride-to-be and realized he had made a horrible mistake. He would later claim that she was unthinkably ugly, and the history books have remembered her ever since as the rejected queen.

Modern historians, however, suggest a far more disturbing reason for his disgust than her face. To understand it, one has to understand who Henry was, how he had clawed his way to the throne, and what he had done to every woman who had failed to give him what he wanted. Henry VIII was not supposed to be king. That role had belonged to his older brother, Arthur, who received all of their parents’ attention while Henry was largely forgotten.

In November 1501, Arthur married Catherine of Aragon, a Spanish princess. Then, in what seemed like the blink of an eye, the strapping fifteen-year-old heir went from healthy to deceased. Henry, the spare, was suddenly the heir to the throne of England. On April 21, 1509, his father, Henry VII, succumbed to tuberculosis, and at just seventeen years old, Henry VIII became king.

One of his first acts was awkwardly simple: he married his brother’s widow. Immediately after the wedding, Henry and Catherine conceived a child. The couple was ecstatic. Nine months later, grief replaced their joy — the child was stillborn.

They were inconsolable. A few months later, Catherine became pregnant again. This time she gave birth to a boy, but their first son, also named Henry, died seven months after his birth. Two more stillbirths followed.

A dark cloud began to grow over the royal household, and the relationship between Henry and Catherine grew more and more strained. Even the birth of a healthy daughter, Princess Mary, in 1516, could not save them. Henry blamed his wife for his lack of an heir and for the unrest in the kingdom. It did not take long for him to take mistresses.

He bedded all kinds of wealthy and important women, but his most famous mistress was Bessie Blount, the daughter of a small-time politician. In 1519, Bessie gave birth to Henry’s son and named him Henry Fitzroy after his father. Most kings who sired an illegitimate child never admitted it. Not Henry.

In a move that shocked the country, he proudly acknowledged the boy as his own. People were baffled, but Henry had his reasons. Before Henry Fitzroy came around, people had started talking about the king. He had been married for a decade and still had no male heir.

In medieval thinking, perhaps 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. Henry had three options. He could somehow legitimize Henry Fitzroy.

He could marry off his daughter immediately and pray for a grandson. Or he could blame it all on Catherine, ditch her, and find someone new. The third option was probably the most complicated and definitely the cruelest. We all know which option he chose.

How did Henry pick his future wife? Easy. He was already sleeping with the beautiful Mary Boleyn. So Henry made the obvious choice: Mary’s younger sister, Anne.

He would soon learn that Anne Boleyn was no easy target. She was young, intelligent, charismatic, and entirely uninterested in becoming yet another of Henry’s mistresses. Despite the unflattering portraits from his later life, Henry was actually very attractive in his youth — tall, athletic, and incredibly charismatic. Women easily succumbed to his charm.

So while Anne Boleyn resisted at first, soon enough she fell right into Henry’s arms. Henry decided to leave Catherine of Aragon and marry Anne Boleyn. There was one giant problem: the Church. The pope was not keen on the idea of a divorce.

Henry tried to convince Pope Clement VII that his marriage to Catherine was invalid, but the pontiff was not buying it. If the king was going to get a divorce, he was going to do it without the Church’s permission. Up to this point, Henry had been an incredibly devout Catholic. He had done a lot for the Church, and they loved him for it.

But nothing was going to stop him from getting what he wanted. 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 but eventually fine. That is 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 of Restraint of Appeals, which essentially said that Rome had zero say in English religious matters from now on. 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.

Henry married Anne Boleyn and got her pregnant before his split from Catherine was even official. He had spent a quarter of a century waiting for a son, and he was done wasting time. Finally, several months after his wedding, Henry had his marriage to Catherine declared null and void. Basically, Henry claimed that since Catherine had married his brother for five months, their own marriage was unnatural.

Strange that he had not thought so all those years ago. Less than nine months after their official marriage, Henry and Anne welcomed a daughter. Henry named her Elizabeth after his mother, Elizabeth of York. He could not hide his disappointment.

After all that work, he was stuck with yet another daughter. There was another problem in their marriage. Henry had found the gorgeous Anne irresistible when he could not have her. Turns out married life with her was a different story.

Anne was stubborn, independent, and had a bad temper — a far cry from the demure trophy wife he wanted. Things continued to go downhill from there. The birth of Princess Elizabeth was a huge disappointment for Henry. Anne got pregnant again soon after, but if Elizabeth was disappointing, the next pregnancy was a disaster.

Anne had a miscarriage in 1534, and Henry was not pleased. Anne Boleyn was not exactly happy with her marriage either, but she was smart enough to know that angering Henry was not in her best interest. She was desperate to give him a son, and some people believed she was willing to do anything to make it happen. Many in England did not believe Anne had had a miscarriage at all; rather, they claimed she lied about the whole pregnancy.

And her sister Mary was still out there, making things a lot more difficult. 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 Henry and Anne were livid, and they made Mary pay for it dearly.

Henry and Anne banished Mary from court forever. Mary went from a life of luxury to utter obscurity overnight. She never saw her sister again and passed a few years later, completely forgotten. In early 1536, Anne Boleyn was pregnant yet again, and aware that if the child was not a son, her days were numbered.

Then, during a jousting tournament, a rival knocked Henry off his horse, leaving him horribly injured. When Anne heard about Henry’s accident, it shocked her so much that she suffered another miscarriage. To put salt in the wound, doctors revealed that the child had been a boy — a boy that could have saved the queen. 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 twenty-eight-year-old Jane Seymour, into swanky new rooms in his palace. In the spring of 1536, Henry 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 witchcraft for good measure. There was essentially no evidence for any of these accusations. The men were executed on May 17. Anne, the Queen of England, was beheaded two days later.

The forty-five-year-old Henry VIII became engaged to the almost twenty-years-younger Jane Seymour the day after Anne’s execution. Their marriage took place only ten days later. For any other king, this would have been a scandal beyond measure. For Henry, it was pretty much business as usual.

Henry VIII’s marriage to Jane Seymour got off to the best possible start. On October 12, 1537, Seymour gave birth to a boy. The birth of Prince Edward finally meant an end to the chaos. But it took less than two weeks for tragedy to strike, throwing Henry’s court into upheaval once again.

Jane Seymour had access to the best doctors in England, but it was 1537, and medicine still had a long way to go. 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.

Henry was heartbroken, but in a way, he got what he wanted. During her agonizing labor, doctors had told the king that it might 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, for other wives are easily found. ”

Jane Seymour’s demise marked a change in Henry.

He began growing morbidly obese and started suffering from diabetes and gout. His mood grew even darker, and he became paranoid and irrational. There were not many people left whom Henry trusted, but one of them was his shifty spymaster Thomas Cromwell. Cromwell was one of the most powerful men in England, until he suggested Henry marry the twenty-five-year-old German Duchess Anne of Cleves.

It seemed like a perfect match, and Anne’s father could prove a vital ally if religious war happened to break out. There was only one problem. Political marriages were well and good, but Henry was not about to marry someone he had never even seen. What if she was ugly?

Don’t worry. Cromwell had the perfect solution. He sent one of the best portrait artists in the world to paint Anne so Henry 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 girl, Henry was finally convinced.

Making their way to London to meet the king, Anne’s party stopped at Rochester. Suddenly, an old, burly stranger entered her room, and everything went horribly wrong. 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. This was not a good idea. Depending on the account, either Henry tried to get Anne’s attention and she ignored him, or he outright tried to kiss her, which understandably horrified the young woman. Either way, it was a disaster.

Henry left the encounter angry, embarrassed, and possibly ready to take revenge. Reportedly, when they actually met, Henry took one look at Anne of Cleves and realized he had made a horrible mistake. Whether it was her looks or her personality, Henry was already looking for an exit before they had even tied the knot. The marriage lasted a whopping six months and, according to Henry, was never consummated.

Henry annulled his marriage to Anne of Cleves and dubbed her the King’s Sister. Thanks to this awkward title, she would end up being one of the rare wives who actually managed to outlive Henry VIII. Anne of Cleves just did not do it for the now-forty-six-year-old Henry. But you know who did?

The seventeen-year-old Katherine Howard. Henry realized that political marriages were not for him and went back to marrying whoever he had the hots for. Not everyone was happy about this latest match. Thomas Cromwell made the Anne of Cleves match happen, only to watch it go up in flames almost immediately.

Then, to make things worse, Henry started chasing Katherine Howard, who was the niece of the Duke of Norfolk — one of Cromwell’s biggest political rivals. Suddenly, Cromwell started to feel the walls closing in around him. In the end, Henry charged Cromwell with treason and a pile of other trumped-up accusations. Despite everything he had done for Henry, Cromwell met the same fate as everyone else who got in the murderous king’s way.

Henry did not even bother to show up to the execution — he was busy getting married for the fifth time. He tied the knot with Katherine Howard the very same day. The timing of the nuptials even allowed Henry to give his wife a particularly nice wedding present: he gave his new queen all of Thomas Cromwell’s lands. It is not like he was using them anymore.

Almost as soon as she married Henry, Katherine began an affair with one of his courtiers, a man by the name of Thomas Culpeper. Since there were 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 had not been in years. He refused to believe the rumors and stood by his queen.

Before she was a queen, Katherine Howard had had an affair with another courtier, Francis Dereham. Strangely, Howard hired Dereham to work for her when she married Henry. Not the best decision. Dereham confessed to having had an affair with Katherine 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 the tables had turned. Katherine Howard did not go down without a fight.

When officials questioned her about Dereham’s claims, she insisted she never cared for him and that he had forced her into an adulterous relationship against her will. Henry charged Katherine, Dereham, and Culpeper with treason and sentenced them to beheading. Of course, Katherine Howard did not take the news well. The nineteen-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. In fact, she would never see the king again. On October 13, 1542, Henry had Katherine and both men beheaded. That made five wives down, two of them by Henry’s own hand.

When it came to women, Henry VIII just could not help himself. In July 1543, Henry VIII wed for the last time. His latest bride was Katherine Parr, and she could not have been more different from Henry’s previous wives. First of all, she was almost age-appropriate at thirty-one years old.

She was also remarkably stable compared to his previous wives. There were no wild cheating scandals or whispered rumors. In fact, Katherine Parr managed to do something none of Henry’s other wives ever did: she made a somewhat decent man out of him. Years earlier, Henry had cut his two daughters, Mary and Elizabeth, out of the line of succession.

They spent the subsequent years in a tense limbo. Parr made Henry bury the hatchet with his two daughters, and he finally brought them back into the line of succession. Without Katherine Parr, England would have missed out on Queen Elizabeth I, one of its greatest monarchs ever. While the young Henry VIII had been attractive and athletic, the old Henry was a different story entirely.

By this point, his waist had ballooned to fifty-four inches, and he could barely even walk. He needed attendants to wheel him around wherever he went. The worst part was the gout, which left him covered in excruciating, pus-filled boils. Mercifully, Henry VIII passed of an illness related to his obesity at the age of fifty-five.

With that, Katherine 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 next to Jane Seymour. After all of his wives, he wanted to lie next to the only wife who gave him a son. And what happened to Henry Fitzroy, the illegitimate son who caused such a stir in Henry’s younger days?

He lived through more scandals than just his birth. Back before Henry had a legitimate heir, he strongly considered acknowledging Fitzroy. This is when a cardinal suggested a twisted solution to the king’s succession problems: marry Fitzroy to his half-sister, Henry and Catherine of Aragon’s daughter Mary. In the end, they did not go through with it.

Henry VIII did a lot of seriously messed-up things, but thankfully, forcing his son and daughter to marry each other was not one of them. Anne of Cleves is now infamous as Henry’s rejected queen. But was it really as simple as Henry finding her ugly and casting her aside? Modern historians suggest a very different reason for his disgust.

When Henry met Anne at Rochester in disguise, she did not recognize him — and she rejected his advances. This was a man who had torn England apart to marry a woman who refused to sleep with him, and who had killed that same woman when she failed to give him a son. He was not used to being ignored. His humiliation at Rochester may have had far more to do with his pride than with Anne’s face.

And Anne Boleyn, the most infamous of Henry’s wives, met an end even worse than people realize. After four days in the Tower of London, Anne gave a letter to her guard. It was addressed to Henry. In it, she pleaded for mercy, writing that never had a prince found a wife more loyal in all duty and in all true affection than he had found in Anne Boleyn.

She also made one final heartbreaking request: she begged him to think of their daughter Elizabeth, and then she humbly asked Henry to spare the lives of her brother and the other men accused of being her lovers. At her core, until the very end, Anne Boleyn was truly selfless. But as we know, it did not go her way. She never stood a chance.

She married Henry VIII, England’s most murderous king.