Henry VIII is one of England’s best-known monarchs. Charismatic and extravagant, his reign lasted nearly 39 years.

Henry enacted radical changes to the English constitution, expanded royal power and broke with the Catholic Church in the English Reformation.

But he is perhaps most famous for having six wives. Though married to his first wife, Catherine of Aragon, for nearly 25 years, Henry’s next five marriages lasted less than that combined.

Best remembered in rhyme form; ‘divorced, beheaded, died, divorced, beheaded, survived’; two of Henry’s marriages were declared annulled, two of his wives were beheaded and another of them died after giving birth to his only son. But his final wife, Catherine Parr, outlived him and their marriage.

Here are Henry VIII’s six wives in order:

1. Catherine of Aragon

Catherine is best known today for her role in sparking the King’s excommunication from the Catholic Church and the Reformation. Married to Henry for a quarter of a century, however, there is much more to her.

The daughter of Spanish monarchs Isabella I of Castile and Ferdinand II of Aragon, Catherine was a political catch.

Betrothed at the age of three to Arthur, Henry’s older brother and the heir apparent to the English throne, her position became uncertain when, in 1502, her husband died just five months into their marriage.

Half of Catherine’s dowry had already been paid to Arthur’s father, Henry VII, so the English king faced the dilemma of how to pay it back.

Catherine was effectively held a prisoner with little money to her name while the issue was debated. But in 1507, six years after Arthur’s death, she became the ambassador of the Aragonese Crown to England.

In doing so, she also became the first female European ambassador in history.

Two years later, Catherine married Henry VIII – who was five years her junior – shortly after he had ascended the throne. This marriage between a man and his brother’s widow required, and was granted, dispensation by the Catholic Church.

The couple’s marriage was eventful for Catherine. In 1513, she served as regent for six months while Henry was away in France. During this time she oversaw an English victory against Scotland at the Battle of Flodden, but she also gave birth to a stillborn child.

Catherine suffered multiple miscarriages and stillbirths. She bore the king’s first child, a boy, only to see him die 52 days later. Her only child to survive to adulthood was a daughter born in 1516, Mary; who went on to become queen.

Catherine suffered another miscarriage in 1518, but one year later Henry had a son by a mistress named Elizabeth Blount. The boy was named Henry Fitzroy, and is Henry’s only confirmed illegitimate child. Blount was not, however, Henry’s only mistress during his marriage to Catherine.

It was his infatuation with Anne Boleyn, one of Catherine’s ladies-in-waiting, from 1526, which set into motion a chain of events that would not only see the end of Catherine and Henry’s marriage, but also lead to England’s Protestantisation.

Henry tried to have his marriage to Catherine annulled to marry Anne. He argued that their marriage had been invalid because of Catherine’s marriage to his brother. Devout Catherine rejected this, saying that she and Arthur’s relationship had never been consummated.

Possibly pressured somewhat by Catherine’s nephew, the Holy Roman Emperor Charles V, the Pope refused. In response the king assumed supremacy over religious matters and turned his back on the Catholic Church.

Henry’s marriage to Catherine was eventually annulled on 1533 and Catherine was banished from court as Dowager Princess of Wales. She lived out the rest of her days at Kimbolton Castle in Cambridgeshire where she died in 1536. Her daughter Mary was forbidden for visiting her or to attending her funeral at Peterborough Cathedral.

Catherine never accepted the end of her marriage to Henry as legitimate, always seeing herself as England’s rightful Queen and Henry’s wife.

2. Anne Boleyn

With the extraordinary events of her life unparalleled in British history, Anne Boleyn is undoubtedly the most famous of Henry’s wives.

Henry may have endured a seven-year courtship and far-reaching political and religious upheavals in order to marry his second wife, but that didn’t stop him having her executed less than three years later.

Anne was born c.1501 to Sir Thomas Boleyn and Lady Elizabeth Howard, and spent much of her youth in France, returning in 1522. She was reported to be fluent in french, a talented musician and to dress in line with French fashions.

Anne was previously betrothed to Henry Percy, but this engagement had been broken off when it did not gain the support of his father, the fifth Earl of Northumberland. Henry VIII, himself, had formerly taken Anne’s sister, Mary, as a mistress.

Anne refused to become the King’s mistress, forcing him to wait through the seven years of courtship until they could marry. In 1532, Henry made Anne the Marquessate of Pembroke, and the pair married formally in January 1533, after a secret ceremony two months earlier.

After going through so much to secure the marriage, the King’s change of heart was likely due to the fact that, like Catherine, Anne seemed unable to bear him a son. After giving birth to Elizabeth I in September 1533, she suffered several miscarriages.

Henry began to look elsewhere for a woman to bear him a son – and he found this woman in Jane Seymour. Anne was less able to accept Henry’s infidelities than her predecessor, and reportedly became enraged and jealous when confronted with evidence of her husband’s affairs.

A month after Henry began courting Jane, he ordered Anne to be investigated for high treason and she was sent to the Tower of London.

After being tried on charges of adultery, incest and treason, Anne was found guilty (most likely wrongly) by a jury which included her once fiancee, Henry Percy. The treason charge alludes to alleged plots to kill the King, but also likely the risk to succession that would be created by a Queen having an affair.

Five men were found guilty of adultery. Among them was Anne’s brother, George, hence the charge of incest. All were executed on Tower Hill.

She was beheaded four days later, on 19 May, on Tower Green. In her final speech she did not admit guilt but instead alluded to her innocence and, perhaps to keep her daughter in Henry’s favour, prayed ‘God save the King, and send him long to reign over you, for a gentler nor a more merciful prince was there never.’

3. Jane Seymour

Henry’s love for – or at least infatuation with – Anne may have sparked the Reformation, but Jane is commonly thought to have been his favourite wife. This is most likely because Jane gave him what none of of his other wives could: a son who lived.

Like Anne, Jane had served as a lady-in-waiting to the queen she would replace. They also shared a great-grandmother. As did Henry’s future wife Catherine Howard.

Jane was not as highly educated as either of her predecessors. Her peaceful and gentle personality, starkly contrasting with that of her predecessors, reportedly lent itself to peacemaking efforts at court – ironic given the circumstances that surrounded her marriage to Henry.

She married the Tudor King in May 1533, just days after Anne had been beheaded.

Her marriage to Henry was overshadowed by the need to give birth to an heir, with some suggesting that this was a factor in the delay of her coronation.

Jane gave birth to a son in October 1534. He would grow up to be King Edward VI, but she would not live to see this. After developing post-natal complications, she died less than two weeks after his birth, aged 29.

Jane is attributed with reconciling her husband to his first daughter, Mary, during their short marriage. Her connection to her step daughter was such that Mary acted as chief mourner at her funeral.

Jane was the only one of Henry’s wives to be given a queen’s funeral, despite never having had a coronation, and was the wife who Henry chose to be buried with upon his own death in January 1547.

4. Anne of Cleves

Henry’s last three wives are less famous than his first three, a matter not helped by the fact that each shares their name with a predecessor.

Not only this but Henry’s last three marriages were far less dramatic than his first three (though this is certainly relative given that his fifth wife was beheaded). None of these final three marriages resulted in any children.

In the case of Anne of Cleves this last point is hardly surprising given that her marriage with Henry went unconsummated. The King proved far less enamoured with his fourth wife than he had with her predecessors.

Henry married Anne in January 1540, though negotiations for the marriage are believed to have begun shortly after Jane’s death in 1534.

The daughter of the Duke of Cleves and Count of Mark, Anne was considered a politically expedient match by Henry’s advisers. She was only just older than Henry’s oldest child, Mary, and had no formal education.

After marrying Anne in January 1540, Henry had their marriage annulled just six months later, citing its lack of consummation as well as his wife’s previous engagement to another man, Francis, Duke of Barr and later Lorraine. Henry blamed the marriage going unconsummated on Anne’s appearance but this slight didn’t stop the pair later becoming close friends.

Anne’s acceptance of the annulment seemed to win her favour with Henry and she subsequently became an honorary member of his family, known as “the King’s Beloved Sister”. Her generous settlement included Richmond Palace and also the home of Henry’s former in-laws, the Boleyns, Hever Castle.

Like Jane, Anne had a good relationship with Henry’s eldest daughter. In 1553 she accompanied her former step daughter to Whitehall, Mary’s new residence as Queen. Anne also reverted back to her former religion, Roman Catholicism, in line with the new Queen.

Anne died in 1557, outliving all of the other five wives and Henry himself. She is the only one of Henry’s queens to be buried in Westminster Abbey.

The political adviser who arranged the marriage did not fare so well, however; Thomas Cromwell was executed on 28 July 1540, the same day that Henry married his next wife.

5. Catherine Howard

Henry’s marriage to Catherine Howard came close to matching the drama of his earlier partnerships – perhaps unsurprising given that his teenage bride was a first cousin of Anne Boleyn.

Catherine’s life had been turbulent even before Henry came on the scene. As one of the many wards of her father’s stepmother, the Dowager Duchess of Norfolk, she began at the age of 13 to be involved in repeated sexual contact with her music teacher, Henry Mannox.

Later, Catherine had become embroiled in an extramarital affair with the Dowager’s secretary Francis Dereham.

After the Dowager Duchess found out, Catherine was sent to court to serve as a lady-in-waiting to Anne of Cleves. This position had been secured for her by her uncle, the Duke of Norfolk, who saw an opportunity in Henry’s lack of interest in Anne. The King was certainly attracted to Catherine’s youth, looks and vivacity.

The pair were married in 1540. In the spring of the following year, however, Catherine is alleged to have begun an affair with a favoured courtier of Henry’s named Thomas Culpeper. Their meetings were reportedly organised by Jane Boleyn, the widow of Anne Boleyn’s executed brother George.

By autumn, rumours about Catherine’s conduct were abundant and the Archbishop of Canterbury, Thomas Cranmer, learned of her alleged affair with Culpeper, as well as her previous relationship with the Dowager Duchess’s secretary, Dereham.

Cranmer saw this as his chance to reduce the influence of his political rival, the Roman Catholic house of Norfolk. He launched an investigation into Catherine’s alleged affairs and she was detained and questioned in November 1541.

Rather than admitting to the earlier affair and possible precontract with Dereham, which would have allowed for her annulment and banishment, Catherine maintained that the relationship was not consensual.

Charged with high treason, both Culpeper and Dereham were executed in December 1541.

In order to find Catherine guilty of a crime, the Royal Assent by Commission Act 1541 was passed. It became treasonous to fail to disclose premarital sexual relations to the monarch within twenty days of marriage, or to incite a person to engage in adultery as the Queen consort.

Within months, Catherine had gone the same way as her cousin Anne, executed for high treason. On her route by barge to the Tower of London she likely have passed under the impaled heads of her reported lovers, Culpeper and Dereham, on London Bridge.

Catherine was probably about nineteen years old.

Jane Boleyn was also executed and both were buried in unmarked graves at the Tower’s parish chapel alongside Catherine’s cousins, and Jane’s sister-in-law and husband: Anne and George Boleyn.

6. Catherine Parr

Henry’s sixth and final wife – and his third named Catherine – was perhaps his luckiest. She married Henry in July 1543, just four months after Catherine Howard was beheaded, and went on to outlive him – though only by a year.

Catherine Parr had been married twice before, being titled Lady Burgh and then Lady Latimer, and married again around six months after Henry died, making her the most married English queen.

This is not Catherine’s only claim to fame: she was also the first queen of both England and Ireland.

The third Catherine had begun a romantic relationship with Jane Seymour’s brother, Thomas, when she caught the eye of Henry. But she considered it her duty to marry the King instead.

In 1546, Catherine, who held strong Protestant sympathies, faced a plot to get rid of her by anti-Protestant officials.

These officials tried to turn Henry against Catherine and even drew up a warrant for her arrest. But Catherine outwitted them and successfully reconciled with her husband, avoiding the same fate as her unlucky predecessors.

She also differed from her predecessors being 30 years old, and a scholar. She became the first English queen to write and publish a book under her own name in 1545, with Prayers and Meditations.

When Henry died in 1547, he left provisions of £7,000 a year for Catherine to support herself, and for Catherine to be treated as Queen Dowager, still in possession of her courtly clothes, jewels and such.

Catherine’s final husband was her previous interest and the uncle of the new king, Thomas Seymour. Seymour is reported to have also had interests in the future queen, Lady Elizabeth, who lived with the married couple.

This rumour was included in evidence which resulted in Seymour’s execution in 1549 for treason This came after his wife’s death, for in August 1548, Catherine had given birth to her only child and died several days later from suspected childbed fever.