This research focuses on the “cavalier perspective” applied in Hieronymus Bosch’s paintings which bears the remarkable correspondence between Renaissance Dutch and Chinese and other Eastern paintings, followed by exploring visual and perceptual notions when it comes to applying perspective in artworks, as well as the shared and differed cultural and national roots and the ties between East and West, projecting the interaction between specific cultures and arts, and uncovering the essence of this novel artistic phenomenon from philosophical, sociocultural, historical, and transcultural perspectives.