This study examines the ongoing hegemony of Orientalism and its “internal consistency” in the representation of Cleopatra. The Western image of Cleopatra so far has been the most celebrated stereotype of the ``goddess`` and the ``whore.`` Cleopatra is understood not only as a powerful and strategic sovereign but also as a seductive femme fatale who caused Antony`s fall. This ambivalence of the ``goddess`` and ``whore`` observed in the figure of Cleopatra originates from Shakespeare`s Antony and Cleopatra. Although many artists and writers after Shakespeare have created a variety of Cleopatras, interestingly, her images oscillate between the ``goddess`` and the ``whore`` from Shakespeare`s ambivalent representation. And such a dichotomous representational system is closely interlocked with the discourse of Orientalism. Based on the mechanism of discursive practice in Said`s terms of “narrative” and “vision” or “manifest Orientalism” and “latent Orientalism,” this study investigates a seemingly subversive representation of the queen in the musical Kleopatra, and its possibility to develop into a counter-discourse against the Cleopatra myth. The findings from this comparative and diachronic study suggest that the hegemony of Orientalism consistently functions in the deep structure, with surface variations only, in the matter of representation of the Oriental beauty.