Christ's admonition to his disciples from Matthew 18:3 appears as the opening of the Gloucester boy bishop's sermon in 1558. The sermon was apparently penned by the cathedral's almoner, Richard Ramsey, who as a long-serving member of the monastic community would have had first-hand experience of the annual ceremony, which in this case took place on Holy Innocents’ Day, December 28. Ramsey undoubtedly knew the custom well and was able to compose the speech from a boy's own point of view. A young chorister named John Stubs had been chosen episcopus puerilis for the occasion, a position usually bestowed by the boy's fellow choristers and ratified by the cathedral's canons. Stubs would have been both excited and honoured at being elected: becoming the “boy bishop” promised not only respect from his peers and the wider community but usually came with a pecuniary reward. Most English boy bishop ceremonies took place either on the Feast of St. Nicholas (December 6), on Holy Innocents’ day (December 28) or some combination of the two, and they marked a high point in that liturgical season of social inversion around Christmas, with “last becoming first” as the youth of the community were granted limited mastery over their adult brethren: “Except yow will be convertyd, and made lyke unto lytill childern”—i.e., “made more like us,” Stubs words would have reminded them—“yow shall not entre in to the kyngdom of heaven.”

For centuries a traditional part of the Christmas season in cathedrals and colleges across England, the Gloucester boy bishop ceremony of 1558 came towards the end of that brief return of such customs under Catholic Queen Mary (reigned 1553–1558). Mary herself apparently hosted the St. Paul's boy bishop in St. James's Palace at Christ mastide 1555. However, the return of such colourful ceremonies was only temporary. They had been prohibited by royal edict in 1541 following Henry VIII's turn to Protestantism, and would be suppressed again under Elizabeth I (r. 1558–1603).