The stanza in which Hoccleve first names himself in the Regiment of Princes is notable not only for the way in which Hoccleve associates himself with Chaucer, but also for the way in which the mention of Chaucer brings with it an immediate commendation and blessing. This stanza not only aligns Hoccleve with Chaucer; it conspicuously affirms Chaucer's good standing in the eyes of a figure who has thus far aligned himself with the institutional church, and who has shown a distinct interest in validating Hoccleve's own religious orthodoxy: the old man. Line 1868 – ‘God have his soule, best of any wight!’ – has the air of an off-hand comment, but it speaks well to Hoccleve's main objectives for Chaucer in the Regiment: to align Chaucer clearly with orthodox Christianity to an unprecedented extent, to marry Chaucer's image with the idea of vernacular literary pursuit, and to apotheosize Chaucer – to put him forth within the social life of the poem as literally ‘best of any wight’. The nature of Chaucer's transformation into the ‘best of any wight’ in the Regiment will be the subject of this chapter.

The narrative conceit that Hoccleve uses in the first section of the Regiment, which he later reprises in his Series, appears to have its roots in Chaucer's prologue to the Legend of Good Women. There, Chaucer is called upon by the God of Love to defend his works and, implicitly, to explain his way of life as a maker of verse. In the Series, Hoccleve is quite similarly called upon to defend both his prior works and his reasons for writing the Series itself, but in the Regiment Hoccleve's approach is more personal: the old man who engages Hoccleve in conversation is more interested in examining the details of Hoccleve's person.