In the midst of the cold war with its accelerating weapons race and in response to an increasingly problematic fragmentation of modern culture, several projects emerged that mobilized the arts for bridging across the gulf separating the „two cultures.“ Among the most prominent count in the US the Center for Advanced Visual Studies (CAVS) at M.I.T. and the Experiments in Art and Technology (E.A.T.) in the New York area. With the CAVS, the Bauhaus teacher and photo artist Gyorgy Kepes crowned his teaching career at an academic engineering institution, whereas the E.A.T. were conceived within industry by Billy Klüver, electrical engineer at Bell Telephone Laboratories, as loosely connected series of collaboration projects between artists, engineers and technicians. Falling roughly in the same time period, a comparison of both crossovers between art, science, and technology reveals important epistemic as well as aesthetic divergences under the overarching sociopolitical agenda of hybridizing arts with engineering: Kepes advertised a universal visual education that was grounded in gestalt psychology and adopted the more recently developed principles of cybernetics and systems thinking as the means for directly addressing, and overcoming, what he regarded as the crisis of the contemporary chaos. Klüver and artists like Robert Rauschenberg, instead, embraced the very fragmentation of the contemporary and engaged in multi media art projects that resulted in fragile, temporary constellations often destined to failure. And consequently, both projects materialized in very different ways – practically, technologically, institutionally, but also politically, aesthetically and materially. Beyond period specific political, personal or technological limitations of both projects, the comparative analysis thus sheds light on the important epistemic differences between these two art-science-technology crossovers that may inform current debate on similar transdisciplinary engagements.