Li Shan was born into a family of scholars and officials in Yangzhou. The wealth and status of Li's family assured him an educational and cultural advantage, including his appointment at court. The subjects Li Shan chose to paint—orchids, bamboo, pines, and flowers—reflected his literati background. Five Pine Trees, painted late in his career, is an unconventional work. Rather than having focused on a realistic treatment of the subject, Li created the trees with an interplay of richly modulated strokes, while he utilized a semicursive script among the branches to illustrate the kinship between painting and calligraphy.