In Italy the first half of the Cinquecento was marked by both flourishing artistic innovation and deep-seated religious uncertainty, the latter revealing itself most clearly in a widespread impetus towards reform. The relationship between these two cultural spheres--long a fraught problem in art historical scholarship--is made visually manifest in the religious works produced by the Florentine painter Jacopo da Pontormo. By re-examining Pontormo's three monumental religious commissions--the Certosa del Galluzzo (1522-27), the Capponi Chapel (1525-28), and the choir of San Lorenzo (1545-1557)--this dissertation maps the complex dialogue between artistic and devotional practice that characterized this era. Further, in highlighting the active role of the painter in this dynamic I propose a not only a new understanding of Pontormo, but also enrich our current notions of artistic agency in the Renaissance period. The foundation of these arguments derives from a re-evaluation of the specific historical context on the one hand, and the implementation of a broader framework of visual culture on the other. Taking its cue from Giorgio Vasari's 1568 edition of The Lives of the Artists, modern scholarship has tended to view much of the art from the early sixteenth century through a post-Tridentine lens; paintings are labeled controversial or heretical, when in fact such notions would not have been relevant in these earlier decades. Published five years after the conclusion of the Council of Trent, Vasari's Lives is predominantly characterized by the author's own attempts to codify artistic pedagogy and style in the service of the Medici Duchy, whose newly consolidated ties with the papacy were of primary importance. A further difficulty presented by following Vasari's example is the relatively narrow view of the artistic environment that his account affords. Aimed as it was towards the social elevation of the individual Renaissance artist, Vasari's narrative undervalues the importance of other genres and media--such as prints, Mystery plays, terracotta sculptures, and sacri monti--to the work of well-established painters like Pontormo. Each chapter examines a single, monumental project, delineating the artist's responsiveness to, and engagement with, the unique devotional and artistic challenges inherent to the individual commission. Chapter One resituates Pontormo's use of the maniera tedesca within the broader contexts of northern devotional practices and the parallels they form with affective strategies employed by other genres including sacre rappresentazioni and sacri monti. Chapter Two focuses on the painter's decision to portray himself the guise of Nicodemus, and the ways in which this identification evoked an entire web of historical associations--linked to hagiographic tradition and local legend--that would have been accessible to contemporary viewers. Finally, in Chapter Three I investigate Pontormo's pictorial approach, which combined an overarching diagrammatic simplicity with a complex, allusive figural language, as a means of communicating to the different levels of Florentine society that would have been his audience in this important parish church.