Edward Said's description of Orientalism as a constitutive element of the modern West is one of the enduring concepts of cultural history. The Orientalism thesis begins with the observation that in the 19th century Westerners began describing the "Orient," particularly the Middle East and India, as a place that was once gloriously civilized but had declined under the influence of incompetent Islamic governments. This construction was then employed to justify Western Imperialism and the expansion of Christianity into Asia. This dissertation examines a case of Orientalism with a twist. Between 1775 and 1830 a group of Anglophone writers and artists depicted Spain as a state with a cultural trajectory similar to that described by the Orientalists. But in the Spanish case, the glorious past was the age of the Islamic Moors who had ruled parts of the Iberian Peninsula from 700 until 1492, while the current Christian rulers were the backwards and religiously intolerant impediments to progress. Thus the case of Spanish Orientalism employs an argument structurally identical to Said's Orientalism, with the role of the Christians and Muslims reversed. In examining this phenomenon, I focus on three particular issues. The first is the representation of the Moors in early modern European popular culture. I argue that these earlier traditions use the Moors as an emblematic manifestation of oppositionality to the centralizing state and elite authority. The romantics found in the Moors a symbol comparable to such other proto-Europeans as the Celts and the Goths, worthy predecessors to the warlike, chivalric, and liberty-loving modern Europeans. The second is the political context of Spanish Orientalism. Like "classical" Orientalism, Spanish Orientalism had a clear political payoff. Its articulators meant to show that the Spanish government was an unworthy steward of its rapidly disintegrating empire, thus Spanish Orientalism is closely associated with attempts to assert Anglophone authority in the Caribbean. Third, I examine in detail the work of the author most clearly associated with Spanish Orientalism, Washington Irving. In the four books he wrote while in Spain during the 1820s, Irving became the individual most responsible for reframing the long representational tradition of the Moors into a modern idiom and bringing it to a mass audience.