We all have our heroes. When he wasn’t busy wooing another wife or closing down monasteries, one of Henry VIII’s favourite pastimes was to dress up as Robin Hood. In fact, early in his reign, the roguish outlaw, famous for his proto-Marxist ideology of taking from the rich in order to feed the poor, was at the centre of a popular national cult. The young Henry, standing over six foot tall, auburn haired and dazzlingly handsome, liked little more on a May morning than to don his hose of Lincoln green and gallivant about the countryside. What the legend represented, though, and its timing, sheds light on Henry’s choice of favourites, as he frequently departed from tradition to promote his intimate servants according to merit rather than birth. Wolsey, Cromwell and even Anne Boleyn, might owe their advancement to the dashing outlaw.

Traditionally set late in the twelfth century during the reign of Richard the Lionheart, stories of Robin Hood’s exploits had survived over three hundred years in ballads and songs. He was a stock figure of medieval literature, appearing in “Robin Hood and the Monk” in 1450, “Robin Hood and the Sheriff of Nottingham” in 1472 and “A Gest of Robin Hood” in 1475. A multitude of records and manuscripts attest to his popularity during the end of the fifteenth century. By the time of Henry VIII’s birth, in 1491, Hood was established as part of the May Day festivities, represented as the May King in pageants to celebrate the arrival of the silly season.

1 May was traditionally a day when the social order was turned on its head. Gender roles and the social structure were reversed in a glorious Bakhtinian carnival, celebrating the formal start of summer. In common with Twelfth Night and our modern April Fool’s Day, it was an opportunity to let off steam at the parish May Ales, by dancing round the maypole and gathering in greenery to make garlands: servants became masters, men dressed up as women and girls were crowned queen. The day also had erotic associations, with one later Puritan writing that three out of four maids returned from the celebrations deflowered. So far so bucolic for merry England.

The young Henry adored dressing up. With his father’s carefully gathered money burning a hole in the new royal coffers, he planned elaborate disguises, with himself and a select band of courtiers appearing in costume, their identities interchangeable and concealed. Even though the figure of the King was unmistakeable, Henry loved the notion that his true self might be temporarily concealed and through a mask or visor, he might flirt with anonymity and be admired for his personal merits rather than his birth. In 1510, he burst into his wife’s chambers dressed, like his men, as huntsmen in green, insisting that they all dance. The most famous of all though, came on May Day 1515, when Henry and Catherine of Aragon rode to Shooter’s Hill with a guard of 200, all equipped in Lincoln green, to shoot arrows and dine on venison in a flowery arbour. Among the cast were Lady May, Maid Marian, Friar Tuck and Little John. It was paradoxically a noble court comprised of figures outside the very laws Henry had sworn to uphold. This romantic nostalgia did not prevent his minions from continuing to dispense savage justice to the convicted thieves and rebels of the sixteenth century.

Yet Henry’s fanciful affection for the noble figure outside the law influenced him beyond his leisure hours and defined his servants’ careers. This belief in the merits of lowly-born men encouraged him to promote certain able courtiers whose origins may previously excluded them from getting close to the King. He had no reservations in giving the top jobs to the son of a butcher and the son of a blacksmith, who had been a self-confessed “ruffian in his youth.” Through the advancement of Thomas Wolsey and Thomas Cromwell, Henry was moving away from the traditional gene pool by which Kings selected their intimates and proving that he could see the merit of hard-working talented individuals regardless of their parentage. These dramatic rises to power, after which Wolsey’s wealth ended up rivalling the King’s own, were underpinned by Henry’s love of disguise, where any man could play the role his mask assigned him, so long as he had the ability.

Wolsey’s father is traditionally identified as a butcher, a cattle-dealer and possibly a casualty at the Battle of Bosworth. From Ipswich School, the boy won a place at Magdalene College, Oxford, and entered the church, before coming to the King’s attention in his thirties. With policies directly opposing the conservatism of the old counsellors Henry had inherited from his father, Wolsey adapted to meet the desires of the war-hungry young man, quickly advancing to Lord Chancellor. His magnificent creation of Hampton Court, more impressive than many royal Palaces, gave rise to John Skelton’s lyric “Why come ye not to court, to the King’s court, or Hampton Court?”

The father of Thomas Cromwell was at different times, a blacksmith, merchant and inn-keeper. During the nineteenth century, his birth place on Putney Hill was still standing, described as an “ancient cottage called the smith’s shop”. Leaving home for Europe, Thomas fought as a mercenary before returning to London, becoming a merchant, entering Parliament and rising to the positions of Principal Secretary and Lord Privy Seal. Both men were part of Henry’s personal policy to promote those of ability regardless of their rank; just as with the Robin Hood pageants, his servants were given an illusion of equality with high-ranking peers. All could enter the stage and play their assigned parts, so long as they continued to please. Once they failed to dance to the King’s tune though, the masks came off. The whole process, in fact, the court itself, was an elaborate extension of the deceptive equality Henry presented by dressing himself up in Lincoln green.

Both Wolsey and Cromwell fell as a result of Henry’s love life. Wolsey was unable to procure the divorce the King required from Catherine of Aragon in order to marry Anne Boleyn; Cromwell’s disgrace came as he attempted to extricate the King from the disastrous match with Anne of Cleves. Ultimately though, their careers were a form of play, an extension of the carnival customs of Merry England, Boy Bishops, May Kings and Queens, who reigned for a day over their own courts, dispensing justice and presiding over entertainments. When they had served their purpose, Henry’s mask came off and the game was over. Wolsey forefeited Hampton Court but the gift was not enough; he was charged with praemunire, serving the Pope over his King, and died on the way to face charges of treason in 1530. Cromwell was executed without trial in July 1540.

Perhaps the most significant example of Henry’s policy was his advancement of Anne Boleyn. At the heart of the May Day ceremonies, a virginal girl was chosen for her purity and beauty, and crowned for a brief period of rule that saw her wishes obeyed. Little more than a figurehead, she was central to this bucolic play, in which lay the fairy-tale transformation of her status. In the Robin Hood legend, the motif of social mobility allows for King Richard I to visit the outlaws and the ideals of loyalty and natural nobility found in the outlaws to be foregrounded against the birth of figures like King John and Guy of Gisbourne. In the 1520s, Henry decided to raise Anne above the position of mistress and make her his wife. Yet he already had one.

Catherine of Aragon, Henry’s partner in the Robin Hood pageants of his youth, had to go. To depose an anointed Queen in the 1530s was a radical move, regardless of the legality of her marriage. Henry’s grandfather had caused a stir by marrying the daughter of a Knight, so when Henry decided to make Anne Boleyn his queen, he was aware that it would not prove a popular choice. The carnival tradition of role reversal was enacted in Henry’s courtly devotion to his mistress and the coronation of a woman whose great-grandfather had been a merchant. Just like Wolsey and Cromwell though, the game only lasted so long as it suited the key player. Anne lost her head three years later.

As with many occasions of social role reversal, the figure of Robin Hood was sometimes co-opted by those wishing to cause trouble. Disguise could be liberating, and this figure of national folklore could represent a darker impulse to the summer celebrations. In 1492, the Star Chamber heard of men acting riotously while dressed as the outlaw and his band, and in 1509, the city of Exeter banned the performance of Robin Hood plays because they led to bad behaviour, as did the Lord Warden of the Cinque ports in 1528. The carnival elements of the legend may have appealed to Henry, but his game was also a dangerous one for those who sought to benefit from its fragile role-reversal.

The cult was less popular after the Reformation, although the story of Robin’s exploits never lost their appeal. As Henry VIII aged, the Lincoln green hero of his youth seemed less relevant. The King lost interest in disguising his identity and enacting stories of chivalry and romance. With the real-life stories of his social climbing favourites ending in tragedy, such legends may have left a bitter taste. With his waistline expanding and his ulcerous leg needing constant treatment, there would be no more riding into the glen for this gargantuan greensleeves.