The most prominent contemporaries of Hebbar in Bombay were the Bombay Progressive Artists’ Group of the time which included artists like F N Souza, S H Raza, M F Husain, K H Ara, H A Gade, S K Bakre et al. Hebbar had grown up amidst a musical environment rich with folk performative traditions like Yakshagana. His long standing friendship with the cultural polyglot Dr. Shivarama Karanth who also hailed from the same region is well-known while Charles Gerard, the dean of Sir J J School of Art Mumbai was a mentor to K K Hebbar who helped him find his individual style beyond mere technical skill. Hebbar’s portraits stand testimony to historical figures, friendships, and professional relationships which existed and constituted the world of the artist and perhaps shaped his worldview. Art historically portraiture has close links with traditions of masks and performative practises closely related to styles such as realism, expressionism, representational and anti-representational modes and so on. An instance of this is evident in the expressionist aesthetic used by Hebbar in his portraiture of his contemporary (member of the Bombay Progressive artists), K H Ara. While some formal traditions of art criticism maintain that the model in a portrait is a mere scaffolding upon which the artist builds up a form, others define it as a ‘biography in a kernel’. His portraits of his creative contemporaries reflect a web of the artist’s kinships that formed and informed his aesthetics.