This chapter explores the transformative journey of fine art painting into the virtual realm, examining how Virtual Reality (VR) is liberating the art form from its traditional constraints. It charts painting’s expansion beyond the flat canvas, highlighting pivotal moments where artists embraced new dimensions and technologies. From the pioneering experiments of the Supports/Surfaces group and Gutai movement to the seamless integration of digital tools exemplified by Hockney’s iPad drawings and Maraccio’s hybrid ‘paintants’, the text illustrates fine art painting’s continuous drive for redefinition. The emergence of VR is positioned as the latest stage in this evolution, offering unprecedented creative capacities while remaining rooted in fine art painting’s rich history, methods, and traditions. VR empowers artists to extend fundamental concerns like colour, form, space, and perception into uncharted virtual territories, representing not a break from the past but an exciting new chapter in fine art painting’s ongoing story.