With the life of the apprentice ever in mind, my work analyzes the underlying social realities of plays such as Dekker's The Shoemaker's Holiday, Beaumont's The Knight of the Burning Pestle, Jonson, Chapman, and Marston's Eastward Ho!, and Shakespeare's Henriad. By means of this analysis, I reopen for critical investigation a conventional assumption about the mutually disruptive relationship between apprentices and the theater that originated during the sixteenth century and has become a cliché of modern theater history at least since Alfred Harbage's landmark Shakespeare's Audience (1941). As a group, apprentices had two faces in the public imagination of renaissance London. The two models square off in Eastward Ho!, where the dutiful Golding follows his master's orders and becomes an alderman, while the profligate Quicksilver dallies at theaters and ends up in prison. This bifurcated image of apprentices arises, I argue, from the national implementation of apprenticeship as a means of social control intended to create a supervisory system over masterless men in response to a century-long expansion of vagrancy. To reinforce this system, there arose a literature of apprenticeship, which included conduct manuals, popular ballads, prose works such as those of Thomas Deloney, and plays like those mentioned above. However, I have found that the crown's encouragement of apprenticeship was not without its perils. If the government wanted young men without better prospects to sign away their freedom for seven years or more, those men needed truly to believe that serving an indenture would elevate their socioeconomic station. If that promise proved false, apprentices would abandon their posts and revert to vagrancy. If it proved true, the widespread upward mobility enabled by apprenticeship would contribute to the formation of a proto-middle class that could exert pressure on the gentry. Thus, apprentices posed a double threat to the traditional societal hierarchy: they were in danger of undoing old lines that divided rulers from the ruled, either by undermining normative power structures through vagrancy or by ascending the social ladder, a prospect offered to induce them not to be vagrants. Critics have long understood apprentice literature as instructive paeans to the redemptive power of honest work and the presumptive realization of individual potential. Characters such as Golding, Deloney's Jack of Newbury, and Dekker's Simon Eyre are extolled as exemplary figures meant to be imitated by audiences and readers, their meteoric success the carrot to entice young men patiently to endure the often grueling labor of apprenticeship. However, that carrot seemed increasingly to recede, as over half of the many thousands of apprentices who began indentures failed to complete them, producing large scale systemic frustration. To stem the tide, a number of conduct books appeared which instructed young men merely to act like good apprentices, with an eye toward future independence and prosperity. This performative aspect might facilitate the rise from apprentice to master, but it also helped masters keep their apprentices content. By falsely acting in a fashion that reinforced a causal link between compliant service and inevitable success, masters could safely enjoy the cheap labor of apprentices without threat of revolt. My work explores how suspicion of the perfidy of apprenticeship and the performance of artisanal identity quietly inheres in the very literature thought to celebrate apprenticeship by providing examples of honest labor and fit reward.