Samuel Sheppard wrote his extended poem The Faerie King as a tragic-epic response to the events of the English Civil War – in particular the execution of Charles I – over a period of at least five years (c.1648–54). This was a time during which, in Sheppard's words, ‘violent hands have made/ England a Den of Dragons’. Much of the work was composed in prison, in particular Newgate Gaol – certainly a den, for Sheppard, of disease and despair, if not quite dragons. Sheppard writes: ‘I languished (surrounded with Dolour, Indigencie, Obloquie with all their Appurtenances) almost fourteene months where my best musick was the ratling of cheines the gingling of Irons, and the groanes of men destind for destruction.’ Elsewhere in the poem Sheppard describes his prison writing context as a place both of literal hunger and of appetite for literary fame:

Literature written in exile or incarceration – such as works by Ovid, Boethius, Malory, or indeed Wilde – often combines nuanced judgement and evaluation with emotional turbulence and anxiety, and The Faerie King is no exception. Arguably the most striking element in this work, which certainly deserves more attention than it has received, is the poem's richly ambivalent portrait of Charles I, depicted in the figure of Ariodant, first prince and then briefly the contested king of Ruina. It was Sheppard's unmitigated support for Charles and the institution of monarchy in the late 1640s, expressed through underground royalist newsbooks, that landed the writer in prison on more than one occasion. In Mercurius Dogmaticus, for instance, Sheppard inveighs against Parliament for sanctioning the imprisonment of the king: ‘Where is our Great and Glorious King, whose Throne they once boasted to elevate above all his Ancestors?