A complex triangular relationship of ideas, naturalness, and emotion is distinctly evident in the artistic practice and theory of Su Shi 蘇軾 (1037–1101), the leading figure exploring ways to expand the expressive capabilities of the graphic arts in the late Northern Song. This article traces the evolution of Su's practice, focusing first on the close relationship with a cousin, the bamboo painter Wen Tong 文同 (1018–79). Examination of communication between the two men sets a historical framework through the decade of the 1070s leading to Su's first exile at Huangzhou. This is followed by analyses of key works of calligraphy related to Su's efforts to give visual form to a discourse on emotions that ironically includes a vocal declaration of the absence of emotions as a philosophical ideal. A final section draws attention to Su's one known painting, Old Tree, Rock, and Bamboo, and ties it to what can be learned from Su's poetic and calligraphic practice.