This article discusses how orientalism has operated and continues to operate within the North American artistic landscape of dance artists. The author starts by focusing on Uday Shankar (1900–1977), one of the major, though often overlooked, figures over the last 100 years of South Asian (and predominantly Indian) dance performance on the concert stage in the diasporic context, to consider how orientalism, the desire for authenticity, a nationalist agenda, religious fundamentalism, economic necessities, multi-cultural initiatives, and diversity desires all interact and coalesce to form an undercurrent of limited potentials about how and why South Asian dance can exist within the American performance discourse. In an auto-ethnographic move, the author then juxtaposes Shankar’s historical legacy with a new artistic project by the author (b. 1969), entitled Reorient the Orient, premiering in 2024. The writing uses archival sources such as photographs, programs, publicity materials, featured essays, newspaper previews, reviews, filmed dance footage, choreographic analysis, and personal reflections to explore how social factors and personal ambitions create awkward relationships within orientalism’s manifestations in the diasporic U.S. performance landscape.