defining moment in his career, and he set about making it the centrepiece of his own personal mythology: his poem Garland of Laurel comprised 1,600 lines in praise of himself. But if he thought it would be a gateway to the salaried job in the royal household that he hankered after, he was to be disappointed. The laureateship was more about making Henry look like a cultivated European monarch than it was about Skelton. While his Latin was good, it was already out of date, overtaken by the new, sophisticated and conversational style perfected and practised in the courts and chancelleries of Europe. More to the point, Skelton didn’t have what Henry looked for in his men-of-letters: the contacts-books, international connections, political and diplomatic know-how that scholars like the Italians Giovanni Gigli, the king’s resident ambassador at the papal court in Rome, and his Latin secretary Pietro Carmeliano brought with them.

But what Skelton did have going for him, apart from unswerving self-regard, was a command of the English language which, as he never failed to point out, made him the direct literary descendant of Chaucer. Taking the time-honoured route of aspiring men-of-letters, he hovered on the margins of court, writing fulsome verses to people who might put in a good word for him in high places. Drifting around Westminster, he made the acquaintance of William Caxton and his Dutch colleague Wynkyn de Worde, who published his poems in cheap editions and employed him as a literary translator. In the preface to his 1490 English translation of Virgil’s Aeneid, dedicated to Prince Arthur, Caxton gave Skelton a glowing public testimonial, praising his critical abilities and his translations from Latin into English, not in ‘rude and old language but in polished and ornate terms’.22 At Cambridge, meanwhile, influential academic friends pulled strings. Not to be outdone by Oxford, the university gave him its own laureateship, which brought him to the attention of its great benefactor, Lady Margaret Beaufort. Skelton, too, had other irons in the fire.

For some years, he had been a familiar figure around the household of Elizabeth countess of Surrey, wife to the powerful Thomas Howard, where he carried out secretarial and administrative duties with decorous formality, perfected his courtly skills, and acted as an outrageously flirtatious tutor to the countess’s daughters and their friends. When in 1495 the Howard family’s rehabilitation into the regime was made complete with the wedding of their first son, also Thomas, to the queen’s sister Anne, Skelton was ideally placed. With his laureateships, his university connections, his friendships with the printers favoured by royalty and associations with noble ladies – foremost among them the queen’s new in-law, the countess of Surrey – he ticked all the boxes for preferment. A ladies’ man through and through, Skelton was perfectly suited to the female environment of Prince Henry’s household. Elizabeth and Lady Margaret, casting around for somebody to teach the prince his ‘learning primordial’, and having perhaps read Skelton’s recent encomium on the prince’s creation as duke of York, evidently thought so too.

Skelton now held a post of considerable importance. As Prince Henry’s ‘creancer’ or mentor, he had power over the development of the young prince’s mind. Appointed the prince’s chaplain in 1498 – he was ordained for the purpose – he also had influence on his soul.23 The educational works he wrote for Henry are a snapshot of the curriculum of the age. They include a ‘new grammar in English’, a Latin grammar with English instructions, and a translation of ‘Tully’s Familiars’, a work by the classical politician-philosopher Cicero, whose Latin prose style was regarded as the ideal model.24 Added to these were treatises on manners and courtesy (‘the book to speak well or be still’), and on government. A flavour of these works – their titles preserved only by Skelton’s obsessive documenting of his own canon – lingers in his surviving Speculum Principis, a ‘mirror for princes’, or guide to behaviour, presented to the young prince at Eltham in late August 1501, which he was instructed to ‘read, and to understand/ All the demeanour of princely estate’.25 But the Speculum Principis shows why Skelton, for all his pride in his role, was ultimately too self-absorbed to be the perfect teacher. A set of second-hand moral exhortations, it has the air of a rushed job, something distractedly thrown together. Among the commonplace, sententious maxims are hints of Skelton’s own vocation: the route to kingliness, it suggested, was through the arts. ‘Do not be mean … Love poets: athletes are two a penny but patrons of the arts are rare.’ Wisdom was to be found in chronicles and histories, which Henry duke of York should commit to memory. He should not take ‘vain pride in riches’, but pursue ‘the glory of virtue’. Skelton was among the first to drum such self-interested advice into the young prince. Many more would follow.26

All the while, Skelton wrote and wrote. The grave tutor and chaplain was also the self-styled ‘wanton clerk’, charming, provocative. He revelled in female company, portraying himself as that must-have accessory, the parrot, ‘with his beak bent and little wanton eye’ fixed lasciviously on the courtly ladies cooing over him and pushing sweetmeats through the bars of his gilded cage. Skelton’s talent, too, began to unfurl in the world of the king’s household, where he was mentioned in the same breath as the man who set many of his lyrics to music, William Cornish. And if his parrot summed up life among ‘great ladies of estate’, another of his characters, Dread, exposed the dark underside of life at Henry VII’s court.

The power politics and intrigue, the edginess and uncertainty of the late 1490s infused the brooding allegory of Skelton’s masterpiece, The Bowge of Court – ‘bouge’ being the salary, board and lodging granted regular servants. In it, Dread has a dream: welcomed aboard the good ship of court by a great lady of estate, Dame Sans-Peer, he is so scared and disorientated by the plotting and ‘doubleness’ of the courtiers he encounters that he throws himself overboard – before waking up. The poem may have come in a long tradition of satire that painted the court as a hell on earth but, printed in 1499, the year of the Warbeck endgame and Suffolk’s first flight, there was no mistaking its topicality. Skelton undoubtedly realized this. In the disclaimer that concluded the poem, he wrote that no reader was to be ‘miscontent’ and that its context was strictly fictional – any resemblance to persons living or dead was, he might have added, purely coincidental. But nevertheless he could not resist adding, with typical audacity, that ‘ofttime such dreams be found true’. ‘Now construe you what is the residue’, he challenged his reader.27

In his carefree existence out at Eltham, this was a world from which Skelton’s young student, Prince Henry, was for the moment insulated. But as the prince grew, there was a crucial dimension to his education that Skelton could not supply. By 1499 Elizabeth was looking for another kind of mentor for her son, an educated, worldly, well- rounded nobleman tutored in the ways of that ‘school of urbanity’, the court – somebody, in other words, like her uncle Earl Rivers, but without the political power and the familial baggage. Then in his early twenties, William Blount, Lord Mountjoy, the prince’s neighbour at Sayes Court, a few miles from Greenwich and Eltham, fitted the bill perfectly.28

Charming and cultivated with a hint of chivalric steel, Mountjoy came from a noble family with a spotless record of service. His grandfather Walter had been close to Edward IV and the Woodville family, while his uncle and guardian Sir James Blount had joined Henry in exile, bringing with him the garrison of Hammes Castle and his influential political prisoner, the earl of Oxford. Mountjoy’s stepfather, the earl of Ormond, meanwhile, was chamberlain to Queen Elizabeth, and it was Elizabeth who was the driving force behind Mountjoy’s appointment as Prince Henry’s intellectual mentor. Her own cultural tastes may have been conventional enough, but she had an enquiring mind and recognized talent when she saw it. And it was Mountjoy who, as the fifteenth century turned into the sixteenth, provided Prince Henry with the gateway to a new world of learning.

Mountjoy had a passion for intellectual culture. After fighting against the Cornish rebels in 1497, he had left for Paris accompanied by his tutor, a young don of Queens’ College, Cambridge called Richard Whitford. There, he immersed himself in a programme of classical learning under the guidance of a former Augustinian monk turned international man-of-letters, the brilliant Dutch scholar Desiderius Erasmus.

On returning to England in 1499, Mountjoy invited Erasmus to accompany him. Ever susceptible to the charms of attractive, well-connected and rich young men, Erasmus had been smitten by his English protege. ‘Lord Mountjoy’, he swooned, ‘swept me away … Where, indeed, would I not follow a young man so enlightened, so kindly, and so amiable? I would follow him, as God loves me, even to the lower world itself.’29 But, it seemed, there was little danger in following his former pupil. Back in England, it was now that Mountjoy took up a post in Prince Henry’s household as his ‘study companion’, as Erasmus put it.

From his townhouse south of St Paul’s in Knightrider Street, among the Bordeaux wine merchants of the cobbled thoroughfare of La Ryole that sloped steeply down towards the Thames, Mountjoy was a familiar presence in the city’s cultural life.30 Through the summer and autumn of 1499 he guided Erasmus through the city’s townhouses, as well as the cosmopolitan intellectual atmosphere of Doctors’ Commons, the civil lawyers’ club on Paternoster Row. What Erasmus found amazed him. As he recollected, he encountered ‘so great a quantity of intellectual refinement and scholarship … profound and learned and truly classical, in both Latin and Greek’. The learning that Erasmus described was that of the humanae litterae, the study of classical

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