The three friends refer to the pine, bamboo, and plum, which represent an age-old auspicious theme. Since the trees grow vigorously rather than wither in the intense cold of the winter, they also symbolize idealized images of men of noble character and lofty scholar-officials, who endure the corruption and problems of the world.
The present painting is recognized as the earliest Japanese example of this theme and, from the activities of the five Zen priests—Gakurin Shōsū (n.d.), Ishō Tokugan (d. 1437), Gyokuen Bonpō, Daigu Shōchi (d. 1439), and Kotō Shūshō (d. 1433)—whose inscriptions can be seen here, the work appears to have been produced some time between 1413 to 1420 (Ōei 20–27). The occasion for the collaborative production may have been a gathering of poetry friends led by the priest Gyokuen, one of the inscribers who lived at Nanzen-ji Temple in Kyoto. Rendered in deep black ink, the two pines standing upright with the plum and bamboo leaning in resemble the style of shigajiku (hanging scrolls with inscriptions written above an ink painting) from the Ōei era (1394–1428), such as in New Moon over the Brushwood Gate (Fujita Museum).