This paper presents a computational framework for critically reinterpreting colonial-era stereoscopic box sets. Using James Ricalton’s China through the Stereoscope (1901) as a case study, we deconstruct its linear narrative using NLP methods for thematic modeling, semantic mapping, and colonial language identification. This analysis informs two complementary artworks in a large-scale 360° VR environment. Cross Eyed offers a guided experience, using the thematic models as lenses for inquiry and visually distinguishing identified rhetoric. Latent Cartographies, in contrast, empowers users to freely navigate the archive’s raw semantic space, fostering diverse modes of experiential engagement with contested heritage. For demonstration visit: https://epfl-emplus.github.io/EntangledGazes/