Henry VIII is perhaps most notorious in English history for his six marriages. He has the distinction in the history of that nation for being the most-married monarch of all time. We have already seen the course of his first marriage to Catherine of Aragon, which was plagued by infant mortality and finished off with a sensational political revolution. His second wife, Anne Boleyn, saw an unfortunate end as well. After the birth of the princess Elizabeth in 1533, Anne suffered a miscarriage and two stillbirths. Henry showed his disappointment openly and determined to rid himself of yet another wife. In May 1536, Anne was charged with multiple instances of adultery–very likely false charges–one of her alleged lovers being her own brother. She was also charged with conspiring to have Henry killed. She and five men were put to death after a quick and unfairly conducted trial on May 19.

Henry remarried very quickly after Anne's execution. Jane Seymour, a quiet- mannered lady of the court, had caught the king's attention while Anne was still queen. She only responded to Henry's persistent overtures after Anne's execution, and the two married on May 30, 1536. Jane bore Henry a son, the future King Edward VI, in October the following year. She died in childbirth, however, and Henry was extremely grieved.

By March 1539, Henry showed himself inclined to marry once again. Thomas Cromwell suggested a possible marriage alliance with the Protestant German duchy of Cleves. Henry sent his best portrait artist, Hans Holbein the Younger, to capture Anne of Cleves's likeness; the painting the Flemish artist brought back to him pleased Henry greatly. Cromwell was asked to conclude the marriage treaty. When Anne of Cleves arrived in England in January 1540, however, Henry was shocked by her plain appearance (Holbein's painting had been too flattering) and her poor manners. He disparagingly referred to her as "the Mare of Flanders," and they were divorced within six months of their marriage, which was never consummated. Anne lived the rest of her days in content obscurity on a large estate that was given to her upon the divorce. Cromwell, who had coordinated the disastrous affair, lost Henry's favor entirely.

Henry's fifth bride was the vivacious Katherine Howard, niece of Thomas Howard, the Duke of Norfolk. After the king married her in August 1540, Norfolk took advantage of his niece's position to gain him and his chief political friend, Stephen Gardiner, the orthodox bishop of Winchester, greater influence with King Henry. Katherine was very free with herself where it came to handsome young men of the court, however, and following in Anne Boleyn's footsteps, she was sent to the scaffold in February 1542, executed for treason.

In July 1543, Henry tied the knot for the sixth and final time. He married the twice-widowed Katherine Parr, a mild-mannered woman who treated her ailing husband and king with great devotion, also serving as a caring, surrogate mother for Prince Edward and Princess Elizabeth. Katherine outlived Henry, who died in 1547.

Henry's many marriages have served as some of the best proof of his egoistic, tyrannical temperament in historical accounts of his life and personality. That he discarded a wife of twenty years (Catherine) because her sons died in infancy, sent two wives to the scaffold for their alleged and real adultery, and treated the unfortunate Anne of Cleves so rudely because of her plainness (when he had grown old, obese, and terribly unattractive himself)–these facts speak for themselves, and do not merit Henry much sympathy. Much of the tragedy in the personal stories of all his wives, excepting Jane Seymour and Katherine Parr, can be attributed to Henry's egoistic disregard for the human cost of his actions.

Jane Seymour was, it seems, the most beloved of Henry's wives. He mourned her 1537 death for a very long time. That her death resulted from the birth of Henry's only surviving son adds particular drama to the story. It may be precisely because of Edward's birth that Henry loved Jane as dearly, and mourned her so grievously, as he did. Very likely his grief was affected by occasional pangs of guilt that his overarching desire to secure a male heir for his throne was, in part, the cause of death to his favorite queen.

The political dimensions of Henry's marriages were integral to their personal dimensions. Catherine of Aragon's fate was bound intricately with that of the English Reformation. Anne Boleyn's daughter Elizabeth, though often looked upon unkindly by her father–who cared to remember her mother as an evil woman who had bewitched him–grew up to wear the crown of England and reign as one of that nation's strongest, and most famous monarchs. Jane, married for love, bore Henry the son he so single-mindedly desired, and the political influence of her family, the Seymours, was considerable at the time of Henry's death and Edward's succession. Anne of Cleves, though not in the manner intended, sealed the fate of Thomas Cromwell, who after losing the king's favor early in 1540, was tried and executed for treason that summer. Katherine Howard's uncle, the Duke of Norfolk, was the major figure of the conservative, catholic faction in Henry's later years, and his star fell not long after his niece's, being arrested at the close of 1546, saved from the scaffold only by Henry's demise. Finally, Katherine Parr was crucial to the salvaging of some domestic tranquility in Henry's final years, tranquility which cannot be underestimated politically.