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’.

Inquisitio, a process first codified in the canons of the Fourth Lateran Council of 1215, was an important means of investigating crime in general and heresy in particular in the later medieval period. For the most part, it has been the subject of historical rather than cultural investigation: scholars have focused on its role in the development of the medieval church and its laws, and on the dynamics of heresy inquisition in medieval Europe and, more recently, England. To view it only as a tool in the fight against heresy, however, is to overlook both its broader significance and its imbrication with other mechanisms of medieval canon law. Even in the English ecclesiastical courts, inquisitio had other uses: it was, for example, most commonly used to regulate sexual relations (fornication, adultery, bigamy, etc.); it was bound up with sanctions like excommunication and public penance, as well as confession, sacramental or otherwise; and, perhaps most significantly, since the law stipulated that inquisitio could only be initiated when someone was widely held to be guilty of a specific crime, it was intimately associated with questions of reputation and social standing. It is hardly surprising then that in the centuries following Lateran IV, the applications of inquisition moved beyond the boundaries of the ecclesiastical courts into the fields of exemplarity, rhetoric and poetry.

In the prologue to his tale, Chaucer's Pardoner gleefully outlines his methods of conning money out of gullible, God-fearing churchgoers with his preaching. From his public stage in the pulpit, the Pardoner employs various methods to persuade his audience to repent—and to part with their money; as he confesses to his fellow pilgrims, ‘myn entente is nat but for to wynne, / And nothyng for correccioun of synne’ (VI.403–04). Here and elsewhere in the Pardoner's prologue, Chaucer places great emphasis on this concept of ‘entente’; indeed, intention seems to be the criterion by which Chaucer asks that we judge the Pardoner. Yet the Pardoner's ability to gull his audience points precisely to the difficulty of discerning intent and of knowing certainly the interior state of an individual, a difficulty addressed at least in part by the sacrament of confession. According to the now-standard narrative, confession after the Fourth Lateran Council (1215) becomes a tool for fostering technologies for ‘making truth inside oneself’ and for generating interiorised subjectivity. In scholarship on medieval heresy, inquisition is likewise understood to have ‘the discovery of truth’ about an individual as its goal and the hidden interior as its terrain.