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The SIX Wives of Henry the 8th

Henry VIII - and his six wives

CONTENT WARNING: this article contains some language, crude humor, and discussions of adult relations.

Henry VIII of England 1491-1547

King Henry VIII of England

“I’m Henry the Eighth, I am, I am…”


Henry the 8th painting

“The name’s Tudor, Henry Tudor…”

Henry VIII was the second King of England of the Tudor dynasty. His father, Henry #7, had become King after defeating Richard the Third, during the War of the Roses, before marrying Elizabeth of York. Henry (the 8th) was one of the only of his male siblings to survive past childhood, because healthcare sucked back then.

Often considered the most selfish and paranoid monarch in English history, the dude wasn’t a big fan of the whole governing thing so often left such nuisances to guys like Thomas Wolsey, Thomas More and Thomas Cromwell, while he spent his time hunting, jousting and sleeping around. Henry’s tumultuous rule was marked by rampant executions and bankruptcy. During his reign, Henry also beefed up England’s naval might, expanded the ‘Divine Right of Kings’, and even started up his own Church after a breakup with Catholicism… all because they wouldn’t let him get divorced.

Which brings me to perhaps the most notable thing about Henry the Eighth: he was practically a medieval pimp. In addition to having SIX WIVES?! throughout his life, it’s estimated that he had at least 12 affairs on the side. All of which is absolutely crazy when you consider that during the ultra-prudish 1400’s, divorce was not really a thing people did in Medieval Europe.

Henry VIII had more ‘Exes’ than Ramona Flowers…

The Six Wives of Henry the Eighth


Catherine of Aragon

Catherine was the daughter of Ferdinand and Isabella of Spain (yup, the very same Ferdinand and Isabella that funded Columbus). Being the loving parents they were, they married her off as soon as they could. At the age of 3 she was contractually betrothed to Henry the Seventh’s eldest son, Prince Arthur. The two young love birds officially tied the knot when she moved up to England at 16.

And then just 6 months later, Arthur up and died – of what might’ve been a fever, because what’s medicine?

One year later she became engaged to Arthur’s younger brother, Henry (the 8th), although he was just a kid, so they had to wait to make it official. However, during that time, his father got into a spat with Spain, and wouldn’t approve their engagement, so after Henry VII croaked, they got hitched in 1509 when Henry the 8th was crowned King.

Catherine and HenryThings went south pretty quickly though: although Catherine did become pregnant right out of the gate, the child was stillborn. Then in 1511 she gave birth to Prince Henry, but unfortunately the baby boy didn’t survive. 2 more failed pregnancies later, in 1516, the Queen gave birth to a healthy baby girl, Mary. Henry’s reaction was not an affectionate one to say the least, saying ‘if it’s a girl this time, surely boys will follow’. They didn’t.

In fact, poor Catherine had at least two other miscarriages.

Meanwhile, Henry was getting busy with his mistresses on the side. It was during this time he sired an illegitimate son, Henry Fitzroy, during an affair with Elizabeth Blount. This convinced Henry that the problem wasn’t with him, but with his wife. That’s when he met Mary Boleyn.

Henry and Mary got jiggy with it several times between 1521 and 1526. To add insult to injury, she was Catherine’s Lady-in-waiting. Realizing that Catherine wouldn’t be able to give him a son, Henry began to consider his options. Then he met Mary’s younger sister, Anne…

"The Other Boleyn Girl" - movie (Eric Bana, Scarlett Johanssen, Natalie Portman)

Decisions decisions…


Anne Boleyn - The Tudors

Anne Boleyn captured Henry’s attention like no one else before. Henry made no secret of his infatuation to the young Anne, whom he would entertain in front of his royal court. He showered her in gifts and jewelry, appointed her as Marquess of Pembroke, gave her higher precedence than the Duchesses of Norfolk and Suffolk, and even brought her along for negotiations with France.

The enamored monarch had grown obsessed with obtaining a true heir (his daughter didn’t count) and Anne just so happened to have the child bearing hips he was looking for. One minor problem: he was still married to Catherine of Aragon…

Anne had a short temper and would often make a scene in front of the rest of the court when she didn’t get her way. Unlike her sister, Anne wasn’t putting out until Henry could put a ring on it, to which Henry immediately requested an official annulment, citing an arbitrary Bible passage from Leviticus (out of context). On behalf of the King, Cardinal Wolsey attempted to appease Pope Clement VII on the matter – his answer? No.

So much no - meme

You see, Catherine was the aunt of Holy Roman Emperor Charles V, so the Pope didn’t want to piss him off and basically told Henry to suck it up.

Being the stubborn macho man he was, Henry didn’t exactly take no for an answer, so went ahead and divorced Catherine anyway by strong-arming Parliament into getting his way. He then demoted his ex-wife from the Queen of England to Dowager Princess of Wales and banished her from his court and even exiled their daughter Mary. Catherine passed away, lonely and heart broken in 1536.

Medieval Cosmo

Medieval Cosmo

Regardless of the political consequences, Henry married Anne in 1533 during a low-key ceremony. Although Henry was head over heels for the new Queen, the people of England were less enthusiastic. The Pope was even less so.

To no one’s surprise, Henry was excommunicated from the Catholic Church for his defiance of the Papal Authority, which led to the English Reformation and the subsequent formation of the Church of England. All because of a horn dog named Henry.

Henry and Anne eagerly awaited their first child. Henry was so excited he prematurely began picking out clothes for his son. However, on September 7th, 1533, Princess Elizabeth was born. Henry was shell shocked. He did not greet his newborn child, he cancelled the celebrations and he went into a deep, dark depression.

Over the next couple years, Anne tried desperately to produce a male heir for her impatient husband to no avail. It was during this time that Henry began having a series of affairs with several women, including both Margaret and Mary Shelton.

Jousting - A Knight's Tale

Jousting: The original extreme sport.

Then, in 1536 everything changed. Henry was involved in a life-threatening jousting accident so severe that it would cause him health repercussions for the remainder of his life. It’s speculated that this injury may have even caused brain damage, leading to even further erratic bouts of insecurity and paranoia. During this downward spiral, Henry began to accuse those closest to him of treason, whether or not there was evidence to support it.

When Anne had a second miscarriage, Henry began to suspect that she was sabotaging him. Sir Cromwell used the situation to his advantage and whispered seeds of doubt into the King’s ear. Trumped up charges of an alleged affair, adultery, incest and even a plot to assassinate him. Anne was arrested and locked up in the Tower of London prior to being publicly beheaded.

Henry was single again…

the beheading of Anne Boleyn


Jane Seymour - the actress (Dr. Quinn Medicine Woman)

oops, wrong one…

Up next is Jane Seymour (no, not Dr. Quinn Medicine Woman). Henry fell madly in love with Jane after becoming disillusioned with Anne. It’s been speculated that it was her family who manipulated her into seducing the frustrated and amorous King. Henry was so infatuated with Miss Seymour that he proposed to her within 24 hours of Anne’s execution! (damn that’s cold)

It was Jane who finally bore Henry a male heir, Edward VI. It was because of this that Henry claimed that she was his one true wife. As fate (and irony) would have it though, she died days later from complications during her pregnancy.

Unlike his previous two wives, Henry gave her the funeral of a Queen.

Jane Seymour - Queen of England


After mourning for a couple of years, Henry got back into the dating scene at 49. His next marriage was a purely arranged one in an attempt to gain favor with the German protestants. He almost immediately regretted it and began looking for ways to send her back. Henry blamed Cromwell for the disastrous mismatch and had him executed for treason. Lucky for her, she got out with her head attached.

Anne of Cleves

She got off easy…


Catherine Howard portrait

16th Century Jail Bait

Henry’s next marital fling was the Duke of Norfolk’s teenage niece, Kathryn Howard. In 1540, despite being young enough to be his granddaughter, Henry took Kathryn as his wife just 16 days after his annulment from Anne of Cleves. There’s not much to say about this one except that after only a year he’d begun to grow tired of her. Rumors began to circle that Kathryn had been promiscuous before their marriage, so of course he had her executed in 1542. Talk about a double standard.


I think it’s safe to say, this guy seriously had a thing for Katherines. This time he hooked up with Katherine Parr, a wealthy widow who would eventually help him reconnect with his estranged daughters in his final years.

Tudor family portrait

Tudor family portrait


Henry’s health declined significantly in his 50’s becoming morbidly obese. Evidence suggests that it was a severe case of untreated Type 2 Diabetes that eventually did him in.

Wilford Brimley - 'One word - Diabeetus'

Wilford Brimley knows best.

Following Henry’s sudden demise, Edward VI (his son with Jane Seymour) was the next in line to rule. Edward was crowned at the age of 9, but fell terminally ill at 15. In 1553, he nominated Lady Jane Grey, his first cousin twice removed, to take his place in 1553, subverting the rightful claims of his half sisters, Mary and Elizabeth.

Queen Mary I of EnglandThis decision did not go over well. Mary, Henry’s (estranged and bitter) daughter from his first marriage, assembled a force of anti-protestant soldiers and deposed Jane before beheading her and claiming the throne for herself. To further secure her position, Queen Mary I married Philip of Spain and then set about ruthlessly enforcing Roman Catholicism throughout her five year reign in which she burned over 280 protestants at the stake, earning her the title of ‘Bloody Mary’!

In 1558 Mary died, childless. The crown passed to her half-sister: the ‘illegitimate’ daughter of Henry VIII and Anne Boleyn, a woman who would change history forever, Queen Elizabeth I

There’s no doubt, Henry the Eighth was a tyrant (and all around selfish *****), BUT his life set in motion events that have shaped our modern world, for better or worse.

'I Regret Nothing.' - Ron Swanson (Parks and Rec quote)

                                 ERIK SLADER

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Henry the 8th Magic card—– More articles on Historic Failure:






“The Six Wives of Henry VIII” – Alison Weir

“The Book of Ancient Bastards” – Brian Thornton

“The Tudors” – Showtime series (2007-2010)

“Inside the Court of Henry VIII” – History documentary (2015)

Erik Slader
Erik Slader
Erik Slader is the creator of “Epik Fails of History” a blog (and podcast) about the most epic fails… of history. With Ben Thompson, Erik is the co-author of the Epic Fails book series. He has a Bachelor’s Degree in Digital Media, once managed a comic book shop, has a weakness for fancy coffee and currently lives in Green Cove Springs, Florida with too many cats.

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