Artists and writers placed the figure of a boy king centrally, using images and stories of historical and biblical child rulers as exempla. This chapter focuses on narrative and artistic traditions of models of child kingship to illustrate the positive cultural associations between childhood and kingship. Scholars have almost exclusively assessed cultural representations of rulership from the perspective of an adult king. But authors used a parallel range of models to contextualise and legitimise a boy’s succession and rule. The chapter looks first at Old Testament kings such as Jehoash and Josiah, then turns to representations of the humble child David, which were especially prominent in coronation ordines and psalter illuminations. Growing interest in Latin, vernacular and visual depictions of Jesus’s childhood is considered in the third section. Interrogating the circulation of these positive biblical models challenges the dominant narrative linking child kingship with disruption and political disorder. The chapter’s final section therefore turns a more rigorous spotlight on the oft-cited Ecclesiastes 10:16 verse which warned that a boy king would bring ‘woe to the land’.