Shi Song was born in Shanghai in 1947. He later moved to Taipei with his family. He attended Taiwan Normal University High School, later gaining a place at National Taiwan Junior College of Arts (now National Taiwan University of Arts). In addition to painting during university, he loved to read translations of Western literary works. In 1967, while still in art school Shi Song and seniors Huang Yung-sung and Yaomeng Jia formed the "Up Painting Society." The group experimented with anti-aesthetic avant-garde creations. In 1971, Shi Song published his first short story, “Story of the Gods”, in "Modern Literature Magazine" (Issue 44), which garnered attention in literary circles.

Aged 25 Shi Song went to Paris to study at the Academy of Fine Arts and Atelier 17. After being
exposed to Western culture and lifestyle in Paris, Shi Song started to rethink his ideas about the link between culture and environment and his ideas about art. He returned to Taiwan in 1975 and worked as an editor at "Lion Art" and "Echo Magazine", where advocated for art and cultural in Taiwan. He was also involved in the planning and editing of many children's books and even adapted three traditional Chinese children's picture story books. In 1991, because of his mother's death, Shi Song began to follow Buddhism. His new ascetic outlook influenced his later art and literature.

For the artist, Thirty-three Guanyin Bodhisttvas Drawings is more like a “conceptual” work of art. It began as a spiritual comfort to soothe the pain of bereavement. However, it has gradually turned into a regular practice of self-restraint and meditation. Shi Song describes it as “a painting of insight meditation.” It puts extraordinary emphasis on the winding lines like silkworm spinning silk, which not only clarifies the inner struggle but also inexplicably creates a pacifying atmosphere of softness.

The abstract movement had already passed its peak before the time Shi Song began university.
During his time at university, there was a brief wave of experimental and anti-aesthetic avant-garde groups working in composite media such as the “Greater Taipei School” and the “Outsider Art Society”. Two important exhibitions of the movement were the "Modern Poetry Exhibition" and the "Formless Exhibition". Influenced by this movement Shi Song rebelled against his college training, and tried his hand at experimenting with art of this type at the end of the 1960s. During the 1970s, Taiwan’s international status was hit by a series of crises, leading to a crisis of national identity and confidence among Taiwanese. Unable to rely on the West, Taiwanese intellectuals began to look to Taiwan to find their cultural footing based on their own land.

After returning from France in 1975, Shi Song became an important standard-bearer of local art and culture. Shi Song saw himself as a craftsman and creating art as a simple activity. From this he developed a philosophy best summed up as "leading the soul with the hand"; he regarded painting or writing as a vocation or way of life. In the late 1980s, Shi Song started to view himself and the world through the lens of classical Buddhist teachings. For Shi Song art became a bridge connecting him to a natural state of being, a way of concentrating the attention and getting back to a primal way of being.