This article investigates the relationship between the philosophy of freedom and the history of art. It maintains that contemplating the two fields together is productive and necessary in understanding some of the compelling interdisciplinary aspects at work in both arenas. Isaiah Berlin’s seminal _Two Concepts of Liberty_ (1958) acts as a touchstone, as the essay establishes the historical and political grounds for uniting the two fields, with other thinkers contributing to the analysis. The ideas discussed correlate the history of art (...) as a narrative of creativity and freedom with art’s political function as it pertains to the positive–negative liberty perspective. These two forces offer a fecund way of thinking about freedom and the arts co-terminally. This essay argues that the creative motivations embedded in the history of art are intimately linked to political motivations, which it is claimed tie the two subjects together both historically and philosophically. (shrink)