In 1490, William Caxton, in the preface to The Boke of Eneydos compyled by Vyrgyle, refers to him as though Skelton already had a scholarly reputation when the book was published.

"But I pray mayster John Skelton," he says, "late created poete laureate in the unyversite of Oxenforde, to oversee and correct this sayd booke ... for him I know for suffycyent to expowne and englysshe every dyffyculte that is therin.

[2] He wrote for his pupil a lost Speculum principis, and Erasmus, in 1500, dedicated an ode to the prince speaking of Skelton as "unum Britannicarum literarum lumen ac decus."

As rector of Diss he caused great scandal among his parishioners, who thought him, says Anthony Wood,[5] more fit for the stage than the pew or the pulpit.

His sarcastic wit made him enemies, among them: Sir Christopher Garnesche or Garneys, Alexander Barclay, William Lilly and the French scholar, Robert Gaguin (c. 1425–1502).

With Garneys he engaged in a regular "flyting," undertaken, he says, [citation needed] at the king's command, but Skelton's four poems read as if the abuse in them were dictated by genuine anger.

The garland in question was worked for him in silks, gold and pearls by the ladies of the Countess of Surrey at Sheriff Hutton Castle, where he was the guest of the duke of Norfolk.

He had already in his Boke of the Thre Foles drawn on Alexander Barclay's version of the Narrenschijf of Sebastian Brant, and this more elaborate, imaginative poem belongs to the same class.

Skelton, falling into a dream at Harwich, sees a stately ship in the harbour called the Bowge of Court, the owner of which is the "Dame Saunce Pere."

Her merchandise is Favour; the helmsman Fortune; and the poet, who figures as Drede (modesty), finds on board F'avell (the flatterer), Suspect, Harvy Hafter (the clever thief), Dysdayne, Ryotte, Dyssymuler and Subtylte.

These figures explain themselves in turn, until at last Drede, who finds they are secretly his enemies, is about to save his life by jumping overboard, when he wakes with a start.

Both poems are written in the seven-lined Rhyme Royal, a Continental verse-form first used in English by Chaucer, but it is in an irregular metre of his own—known as "Skeltonics" —that his most characteristic work was accomplished.

[citation needed] The Boke of Phyllyp Sparowe, the lament of Jane Scroop, a schoolgirl in the Benedictine convent of Carrow near Norwich, for her dead bird, was no doubt inspired by Catullus.

By the end of the 16th century he was a "rude rayling rimer" (Puttenham, Arte of English Poesie), and at the hands of Pope and Warton he fared even worse.

His own criticism is a just one: For though my ryme be ragged, Tattered and jagged, Rudely rayne beaten, Rusty and moughte eaten, It hath in it some pyth.

[2][7][8] He exposes their greed and ignorance, the ostentation of the bishops and the common practice of simony, taking care to explain the accusations do not include all and that he writes in defence of the church.

"Jemmy is ded And closed in led, That was theyr owne Kynge," says the poem; but there was an earlier version written before the news of James IV's death had reached London.

"Howe the douty Duke of Albany, lyke a cowarde knight" deals with the Campaign of 1523, and contains a panegyric of Henry VIII.

Thomas Warton in his History of English Poetry described another piece titled Nigramansir, printed by Wynkyn de Worde in 1504.

The Garlande or Chapelet of Laurell was printed by Richard Faukes (1523); Magnificence, A goodly interlude, probably by John Rastell about 1533, reprinted (1821) for the Roxburghe Club.

Hereafter foloweth certaine bokes compyled by mayster Shelton ... including "Speke, Parrot", "Ware the Hawke", "Elynoure Rumpiynge and others", was printed by Richard Lant (1550?

Five of Skelton's "Tudor Portraits", including The Tunnying of Elynour Rummyng were set to music by Ralph Vaughan Williams in or around 1935.

The four others are "My Pretty Bess", "Epitaph of John Jayberd of Diss", "Jane Scroop (her lament for Philip Sparrow)", and "Jolly Rutterkin."

[citation needed][9] Sir John's daughter, Mary Shelton, was a mistress of Henry VIII's during the tenure of her cousin, Anne Boleyn.

This comparison may have been a double entendre, because Cressida, as depicted by Chaucer in his work Troilus and Criseyde, was notable as a symbol of female inconstancy.

[11] A popular but unverifiable legend suggests several poems were inspired by Margery Wentworth; she is noted as one of the women portrayed in Skelton's Garland of Laurel.