In 1968, amidst critical debates about objecthood in the history of postwar sculpture in New York, Louise Bourgeois fashioned five bronze sculptures hung from wire and titled Janus. The pieces germinated from a series of soft, viscous, dripped, and piled horizontal objects displayed sans bases on a table top or directly on the floor. Included in Lucy Lippard’s pivotal Eccentric Abstraction exhibition in 1966—focused on the liminality of anti-sculptural and sensuous materials such as latex, wax, and fiber—the radical nature of such work announced Bourgeois as a figure to watch during that unstable decade. Formed by plaster poured into flexible molds, and then cast in permanent bronze, the ludic Janus sculptures evoke sexual reproduction, bodily thresholds, tumescence, and tactility while also registering affects of desire, aggression, ambivalence, and melancholia. The Januses are double-faced like their phantasmagorical namesake, the Roman deity of creation and city gates who could gaze both forward and backward, further emphasizing their dialectical structure. Made at a turning point in late modernism that positioned sculpture’s status as a “specific object” and one critically engaged with the expanded fields of time and space, the history of Janus entwines the aesthetic, the phenomenological, and the psychoanalytic. Bourgeois conceived her sculptures as whole, autonomous objects (even when cannibalized from cognates and soldered together) within the dynamics of physical and psychological perception. A serious student of psychoanalysis, her approach calls forth not only formalist procedures of contiguity and asynchrony, but a framework of object relations put forth by W. R. D. Fairbairn, Michael Balint, D. W. Winnicott, and Heinz Kohut—psychoanalysts who contended that the aesthetic object functioned as a restored and numinous object in the emotional life of the beholder. As distinguished from ordinary objects, enlivened aesthetic and cultural productions resonate with the indelible fantasy objects of interior space. Both types of objects—those of the inner and outer worlds—comprise symbolic reconstructions, and as such, generate multifarious meanings for artists and beholders, often difficult to pin down. This paper explores Janus as a courier of fantasy and reality along the margins of what Winnicott called transitional or intermediate space. The site of play and creativity that catalyzes the being and doing of the self and others, his understudied ideas surrounding transitional space expand disciplinary boundaries of aesthetic reception, and especially, empathy.