This dissertation interrogates correlations between imperial expansion and the history paintings produced for London audiences by the American-born artist Benjamin West (1738-1820) during his first decade in England (1764-1774). Within that ten-year span, Grand Manner academic history painting shaped and reflected the imperial anxieties that elite Britons experienced as a result of dramatic territorial gains, consolidations and losses in North America and South Asia. To follow the trajectory of history painting’s rise, relevance and obsolescence is to track Britons’ negotiation of their global status as a “free though conquering people.” As England’s pre-eminent history painter, West secured for himself a place within the discourses of the imperial self-imaginary by developing two types of iconographic program. First, the selective appropriation of narratives from classical antiquity allowed West and his patrons to inculcate their audiences with visual models for British imperial virtue. Advancing the cause of imperial self-ratification through classical narrative, West cast the English as the natural heirs to the Roman empire. The resulting images paralleled and buoyed contemporary textual discourses of empire and intersected with antiquarian collecting practices, both of which were based on the notion of modern British proprietorship of classical antiquity. Second, developing and refining a model introduced by Francis Hayman (1708-1776) at Vauxhall Pleasure Gardens in 1761, West contrived a pictorial format which introduced persons living and recently dead into a realm of visual expression formally reserved for characters from biblical and classical textual sources. Invoking some of history painting’s most familiar compositional and figural conventions, West recombined history painting, portraiture, landscape and genre to formulate the iconographically hybrid heroics of empire, complete with its own set of pictorial motifs through which West and his followers styled their subjects exemplars of classical imperial virtue. Imperial anxiety afforded history painting its short-lived relevance among English-speaking audiences during the second half of the eighteenth and first quarter of the nineteenth centuries, and imperial self-acceptance rendered that most highly-esteemed of artistic genres obsolete. Through the visual heroics of empire, Benjamin West established history painting as a viable form of Anglophone cultural production during his first decade in London.