This chapter explores the evolution of painting as it has transitioned into the digital realm, marking a significant shift from early computer painting systems of the 1980s to the emergence of post-internet aesthetics. It highlights early digital pioneers who adapted traditional styles to the new digital tools. It is argued that the convergence of analog and digital cultures has fundamentally altered artistic practices, making materials and tools more reproducible, manipulable, and shareable. This shift has also sparked critical discourse, questioning the concept of originality in the digital age. Virtual Reality (VR) painting is a rapidly evolving field, with artists exploring new possibilities and institutions increasingly recognizing its significance. VR artists have blended digital aesthetics with traditional artistic concerns, showing the potential for new forms of artistic expression and audience engagement. Ultimately, the integration of digital tools represents a profound transformation in the artistic creation and viewer experience of fine art painting.