Chan paintings, as the name suggests, are artworks related to Chan. It is generally recognized that Chan painting originated in the late Tang and the Five Dynasties, developed in the Song Dynasty, and matured in the Mongolian-ruled Yuan Dynasty. The art form was brought to Japan along with the Chinese Chan School to be known as Zen. It had a pinnacle of development in the Ming and Qing Dynasties, and the first half of the twentieth century made another important turning point, becoming worldly popularized. In this long course of history the Song-Yuan era formed an important transition for the art's development. Chan practitioners of the period made such paintings from as a way to express a poetic state of mind or to take load off one's chest to art pieces infused with Chan spirit, not limited to conventions, beyond imagination, yet simple and straightforward. Therefore, they can be called paintings of one's experience of Chan state of mind. This article is to explore the development of these paintings in the Song-Yuan era in terms of the presentation, techniques, and as well the delivered state of Chan.