The poetry of John Skelton occupies an uneasy position in time. Unclaimed either by medievalists or by early modernists (or at least fervently claimed by neither), his canon has been relegated by contemporary periodisation to the no man's land between the late medieval and early modern periods. While aspects of his style and choices of genre recall medieval trends, his politically themed verse reflects the controversies of his own time, controversies in which he was sometimes personally embroiled. He claims to work in the mould of the great English poets of the medieval period – Chaucer, Gower, and Lydgate – while anticipating developments such as the fascination with fame and immortality that are often deemed characteristic of Renaissance verse. Consequently, he has come to be viewed, in the words of one critic, ‘as a transitional figure within modern accounts of literary history and periodization’.

Skelton's marginal position in time mirrors the shifting temporality that accompanies his preoccupation with his laureate status. In the prologue to his Eneydos (published in or around 1490), William Caxton describes ‘mayster John Skelton’ as ‘late created poete laureate in the unyversite of oxenforde’, a title he seems also to have received from the University of Louvain by 1492, and from the University of Cambridge in 1493. As Skelton's modern biographers have noted, these titles reflected an academic achievement in rhetoric rather than what early humanists or modern readers would understand by either ‘poet’ or ‘laureate’. Nevertheless, Skelton's oft-remarked reiteration of these titles throughout his corpus is indicative of his investment in them, an investment that Seth Lerer, among others, has argued borders on obsession. Moreover, as Skelton's most thoroughly laureate poem, The Garland of Laurel, demonstrates, his ambition seems to have been to imbue the purely academic title with all the classicised lustre associated with the title awarded to Francis Petrarch (1304–74), which – as Petrarch's own coronation address noted – linked laureate poets to the performance of a specific task: ‘the memorialization of the glory of those whom they serve’.