For 500 years, the work of the Horenbout family of Flemish artists at the Tudor court (fl. 1522–1548) has played a supporting role in art histories. Foundational in the creation of the English miniature tradition and initiators of repetitive portraiture employed as a political tool, they have taken a back seat in the literature both to contemporaries like Hans Holbein and to those who came after. Yet the Horenbouts—paterfamilias Gheraert, daughter Susanna, son Lucas, daughter-in-law Margaret—were principal players in the visual campaigns of propaganda and self-promotion undertaken by Henry VIII, his successive queens, Cardinal Wolsey and the 5th Earl of Northumberland. Creators of many of the images and symbols that became the common currency of Tudor identity, the Horenbouts were the starting point for the emerging mask of royalty, the way in which the Tudor monarchy presented itself visually to the world. By analyzing and contextualizing a set of diverse works, some attributed to the hand of “Horenbout”, others that should be added to the catalogue, this paper examines how the family workshop created representational change, moving Tudor art from the medieval to the modern, and in the process identifying a broader pool of patrons than has yet been recognized.