I’ve just finished reading “Henry VIII; Virtuous Prince” by David Starkey. He’s been writing and presenting TV shows about the Tudors for nearly 40 years now having started his career with his Cambridge University thesis on Henry VIII. In my opinion Starkey is the go-to guy for all things Henry VIII if anyone is interested.

The main things to remember about Henry are these: firstly that he is two people. The first half of his reign he is very much a late Medieval monarch in the same way that Richard III, Edward IV and especially Henry V was in the 100 years or so preceding him. The things he valued and excelled at were all traditional. He is tall and strong and athletic, a genuinely prodigious jouster and real tennis player, he trains in mock combat nearly every day. He is pious and traditional in his piety. He adores his wife. He is appropriately warlike and plays his rival kings against each other well. He has a group of similarly minded companions (notably his best pal Charles Brandon who marries his sister) and leads his barons as a first among equals very much in the mould of hero kings Edward III and IV.

He starts to change his personality in the 1530s, with 1536 being the year in which he changes for good. He comes off his horse in a jousting accident and is rendered unconscious for a large part of an afternoon, Anne Boleyn miscarries a baby boy with the stress of the uncertainty to the Kings’ life. Later that year he has her executed - accused of infidelity with her brother, her music teacher Mark Smeaton and others. He doesn’t even attend her trial or execution. From this point in he is the cruel, cold, corpulent king of the history books and famous Hans Holbein portrait. It is only the last 11 years of his 56 year life, but it creates the enduring image which we all associate him with.

The second thing about Henry to remember can be summed up by this quote from Starkey: “a man who marries 6 times either does not take marriage seriously, or takes it too seriously” I agree with this argument, following Starkey’s evidence that Henry genuinely loves all of his wives (except no. 4; Anne of Cleves who he has been ‘tricked’/manipulated into marrying, famously roaring to Cromwell the day before their marriage “I like her not!” )

Henry’s legacy as “Henry the Great” as contemporaries would have called him is solidified as impressive and all powerful in the generations after his death because the world has changed from a medieval one into an early modern/renaissance one. He is followed by his 9 year old son Edward VI and suddenly it is not an all powerful king in charge, but a bickering group of his councillors. When Edward dies at 15 years old a 9 day Protestant coup is defeated by Mary Tudor and her Catholic faction of councillors. Here again, in a religiously divided England the memory of an all powerful king would have been a fond one. Particularly when Mary marries the Spanish King Philip II, which was very unpopular amongst a large section of her subjects. Next up we’ve got Elizabeth, daughter of Anne Boleyn, who’s convoluted claim to the throne relies on her direct line from Henry VIII. The memory of her father gives her the legitimacy to become monarch and her careful trust in a selection of brilliant councillors keeps her there. My personal theory is that a king of England would not have been as successful as Elizabeth in this period, as a king would not have been expected to defer to his councillors in the way that she did so successfully.

Shakespeare is writing towards the end of Elizabeth’s reign and he is careful in his ‘history plays’ to show Tudor ancestors in a good light, and those who oppose these characters or usurp the throne in a bad one. During a showing of Richard II (in which the monarch is deposed) Elizabeth remarks that she fears that this might be seen as an allegory for her own reign (“know ye not? I am Richard II”)

By the time we get to Elizabeth’s successor James I, the times have moved on enough to make Henry’s rule feel old fashioned and barbaric. Though it is notable that in Shakespeare’s Macbeth, (first performed 3 years into James’ reign) that the witches spell sequence in which MacBeth is shown the line of future kings does not feature Henry or any of the Tudors as precursors to James (who does feature)

In conclusion: Henry lived long in the memory of the generations that followed him, because he was an impressive and powerful ruler who would have been remembered fondly in the religious conflicts that were to follow him. Today we remember him differently because our sensibilities have changed AND because we only remember the sensational things that he did post-1536.

In addition to the excellent previous answer, some other elements need to be addressed.

Firstly, in matters of health, Henry seems to have suffered a variety of maladies separate to the near death experience he experienced at jousting. Some have suggested he suffered from syphilis, but the evidence seems to suggest otherwise (during his reign aside from his wives Henry only had three mistresses, Elizabeth Blount, Mary Boleyn and Margaret Shelton).

In 1527 he tore a tendon during an especially vigorous game of tennis, requiring him to wear a black velvet slipper to ease the pain and weakening the foot that the tendon tore again in 1529. Around a year after the foot injury he had his first varicose ulcer on his left thigh that distressed him greatly.

He seems to have suffered repeated bouts of these that may well have caused chronic osteitis, a very painful bone infection. This would flare up as the underlying infection wasn’t dealt with causing his legs to become further ulcerated and producing a most foul stench.

He also suffered from chronic constipation, and all of this before the jousting injury mentioned in the previous answer in 1536. As well as leaving him briefly incapable of speech, the impact probably tore open the varicose ulcer he had been treated for previously. Two years on he seems to have suffered a deep vein thrombosis.

He didn’t help matters after the death of Jane Seymour by gorging himself in rich food (which utterly ruined his digestion and caused the prestigious weight gain). He grew so large, his legs so weak that ten years later that special chairs had to be ordered in to carry him around at least one of his palaces (court records called these ‘trams’ which were probably sedan chairs with wheels).

Henry became a man in constant pain, obese and suffering from agonising ulcerated legs. This was carefully hidden from the wider world to a degree but all feared the Kings foul temper and as he aged, an evil distempered viciousness of mood would take hold of him (he once had an argument with Katherine Parr that almost led to him burning her for heresy and by all accounts he was engaged in a rather cruel game to force her to submit to his arguments on matters religious).

The fact his eyesight was failing him and the glasses ordered for him from Germany kept getting lost- probably by him, did little to alleviate this foul temper of his.

What is forgotten however, in answer to the question set, was Henry’s popularity was not just based upon loyalty to the King. By circumstance rather than plan, Henry changed the very nature of England, creating huge social changes that often get overlooked in the focus upon his marriages and his religious issues.

Far more than any King previously, Henry seems to have opened the way for the rise of a new class of courtier; not aristocratic, these men were ambitious, loyal, more politician than courtiers, and they would rise and fall as the Kings favour waxed and waned. Obviously the most famous are the likes of Wolsey and later Thomas Cromwell, but to them must be added the likes of Thomas Henaege, and above all Anthony Denny. These men, members of the privy council, advisors and confidants (and also victims of Henry’s mercurial and swinging moods) represent a much greater change going on in England.

The best representation of said changes could be found on the very streets of London itself. It is often overlooked when discussing Henry’s seizure of monastic lands that large parts of London were owned by religious orders. When these passed to the Kings hands he had sold them in for profit very quickly (often so hastily he forgot to change the legal codes for the areas leaving some, like Blackfriars, operating under Church Law without the Church being set to enforce it). These areas were bought up by enterprising men who would erect hastily built housing gaining profit from becoming land lords and gaining wealth and social standing.

This huge property explosion then drove the explosion in the size of London and allowed a new class of gentleman begin to make their mark. To men like these? Henry was beloved as he had empowered them.

Another example had been Henry’s purge of perceived rebellious landowners in Devon and the south west. Previous to this political power in Devon had been vested in landowners in the centre of the vast county. Henry’s show trials decimated their ranks and the centre of political power shifted to a new class of gentlemen based on the coasts, especially Plymouth. In time this would produce the likes of John Hawkins, Francis Drake and Richard Grenville.

Again because his politics had allowed rise in rank by these families, Henry was seen in an extremely positive light for some generations to come.

While he had dragged England through an exceptionally tempestuous period; failed at any military campaign of worth (although his scorched earth policy kept the Scots in check); had mostly grave bad luck in women; and was a myopic, vicious, capricious old man capable of inflicting grave cruelty upon his subjects, Henry was also seen as a success.

He had secured a son to continue his line; he had stamped royal authority upon the kingdom in a way even his father had failed to do, securing Tudor fortunes; he had empowered a new class of Protestant businessmen, whose influence was to be seen over the coming decades; he had created a system wherein men of learning and wit could rise in royal patronage and he had projected an image of strength throughout his reign (if it this transforms form manly martial vigorous strength of his youthful days, to cold brutal cruel strength of his latter days).

For all these reasons he was seen as a successful king at the time, and after the death of his son, was fondly remembered as England faced two queens in succession. Certainly Elizabeth used her lineage to great effect in her reign.

Away from Starkey, I would heartily recommend ‘The Last Days of Henry VIII’ by Robert Hutchinson; his extensive use of primary sources presents an incredibly detailed, intimate insight into the King; for a better idea of the changes he inflicted to the city of London, John Stows ‘Survey of London’ in 1603 is an invaluable guide; John Julius Norwich ‘Four Princes’ also helps by placing him in the context of other rulers in Europe at the time.