This paper examines the relationship between art and Judaism, focusing on the distinctive context of Livorno over three centuries, from the Grand Duchy of Tuscany to the Unification of Italy. Beginning with the Medici period in Seventeenth century, it investigates the presence of Jewish painters and even Jewish draughtsmen who actively participated in the field of natural science, benefiting from both the absence of a ghetto and the religious openness within their community. While observing religious holidays — which occasionally required them to justify extended periods of inactivity in October — Jewish artists collaborated with Christian counterparts in a cultural exchange that influenced both communities. It was not until the 19th century, however, that a formal debate on the role of Jewish artists and collecting practices emerged. National journals such as the Vessillo Israelitico (1874-1922) served as a platform where local and national rabbis deliberated on suitable themes for Jewish painters and sculptors, as well as for Jewish art collectors. An analysis of the journal's issues, including insights and recommendations from Livornese rabbis such as Dante Lattes, Giuseppe Cammeo, and Giacomo Mosè Montefiore, invites a reexamination of the complex relationship between Judaism and art, a subject often treated simplistically in existing scholarship. As this study underscores, rabbinical authorities in Livorno and Italy never wholly rejected figurative art. Instead, a more rigorous scrutiny of what aligned with Jewish religious and cultural values began to emerge after the Unification of the country, driven by growing concerns over the assimilation of Jewish communities and the potential loss of their cultural identity.