Originally, Autumn Landscape and Winter Landscape were passed down in the Kyoto temple Manshu-in as Summer and Winter Landscapes, and it is thought that these were two of four scrolls depicting the theme Landscapes of the Four Seasons. Sesshû (1420-1506?) studied many modes of painting, including those of Muromachi-period Japanese painter-monks Shûbun and Josetsu, as well as various masters of the Southern Song dynasty (c. 1127-1279), and of the Zhe School of the Ming dynasty (1368-1644), however, the stable composition and strong brushwork of these two scrolls demonstrate Sesshû's individual style.
In Autumn Landscape, Sesshû reveals a steady recession into pictorial space: he depicts a winding path following the flow of water from the bottom left of the painting, on which he conspicuously places two people engaged in conversation, with the buildings and mountains in the distant. The motifs are gathered at the bottom, while the upper portion of the painting expands infinitely, in strong contrast to Winter Landscape.
In Winter Landscape, a snow-laden cliff occupies the center of the painting, and a single figure, who has just disembarked from a boat, climbs towards the buildings. The powerful contour lines of the overhanging cliff and the barren winter trees evoke a sense of bitter cold. The composition, which places rocks and mountains in a counterclockwise spiral from the bottom left corner, strongly conveys the contrived structure of the painting. Along with the strong quality of the brushwork, this composition intentionally contradicts the sense of deep recession into pictorial space.