This dissertation examines the role that Bologna’s university, the first inaugurated in western Europe, played in shaping the city’s visual culture at the turn of the sixteenth century. Originally founded to provide instruction in civil and canon law, by the late fifteenth century students came to Bologna to study disparate fields, including the studia humanitatis, medicine, the notarial arts, grammar, logic, astronomy, and theology, among others. Artists enjoyed ready access to Bologna’s large faculty and to the networks of courtiers, nobility, and antiquarians associated with the city’s intellectual elite, which was concentrated around the court of Giovanni II Bentivoglio (1443–1508). Through three case studies, this dissertation establishes how artists and professors collaborated to create a uniquely Bolognese visual vocabulary that celebrates the scholar as an heir to ancient knowledge, and as a nurturer of future generations.My analysis of works in various media produced by a generation of local, stylistically diverse artists, including Francesco Francia (1447–1517), Lorenzo Costa (1460–1535), Marcantonio Raimondi (c. 1470–c. 1534), and Amico Aspertini (c. 1474–1552), demonstrates the breadth and character of the university as a catalytic force of artistic creation. Weaving together iconographic interpretation with analyses of humanist literature, city chronicles, and scholarly treatises, this dissertation demonstrates how artists participated in university discourse and debate. Chapter One introduces the history of Bologna’s university, how it shaped and was shaped by local political and intellectual forces, and its position within the wider context of early modern Italian universities. Chapter Two explores how Bologna’s characteristic porticoes shaped civic engagement with the university and with painting. Chapter Three charts the history of scholars’ tombs as originators of the city’s most recognizable iconographic convention: images of seated professors lecturing to students. Chapter Four focuses on Amico Aspertini’s portrait of philosopher and physician, Alessandro Achillini (1463–1512), showing how the work engages both local iconographic traditions and wider contemporary debates in Italian portraiture. In this first integrated consideration of late Quattrocento Bolognese art history, I show how picture-making and university scholarship were deeply intertwined, forming an essential feature of artistic expression and life in Bentivoglio-era Bologna.