Wayne Thiebaud recalled being “fascinated, living in San Francisco, by the way the different streets came in and then just vanished. . . . No one view seemed to get this sense of edges appearing, things swooping around their own edges, that I loved.” Thiebaud’s vertiginous streetscapes reflect some of the anxieties of the modern age, their dizzyingly surreal vantages conveying a sense of the precariousness, fragility, and absurdity of human existence. Reflecting the impacts of human encroachment on the landscape, "Diagonal Freeway" compresses a dramatically vertical cityscape and barren stretch of hillside into the upper quadrant of the composition. The rest of the painting is dominated by the roadway’s striking geometries and vast expanse, against which the shadows of a few solitary vehicles are silhouetted as they ascend an impossibly steep incline.