Sir John Oldcastle, a prominent Lollard leader and former companion of Henry V, led a failed uprising in January 1414 that represented the most serious armed challenge by religious reformers in medieval England. Lollardy, the heterodox movement inspired by John Wycliffe's theology, advocated lay reading of scripture in English and challenged clerical authority, generating an extensive underground literature of vernacular religious texts. After the revolt's collapse, Oldcastle evaded capture for years before being executed in 1417. The episode marked a turning point after which Lollardy went underground, continuing as a persistent current of dissent that would eventually converge with Protestant ideas in the sixteenth century.

The Lollard movement's insistence on vernacular scripture created a parallel literary culture of English religious prose and verse that challenged the Latin monopoly of the Church and shaped the trajectory of English writing. Wycliffe's Bible translations — circulated illegally — habituated English readers to vernacular sacred text in ways that would influence Tyndale and eventually the King James Bible. Oldcastle himself became a complex literary figure, appearing (transformed) as Falstaff in Shakespeare's history plays, illustrating how political and religious dissent was later transmuted into dramatic and poetic character.