The Expressionist period of art featured bright, exaggerated colors and lines, representative of the artists’ own feelings and ideas rather than an objective view of reality. Two artists of this period, James Ensor and Emil Nolde, produced aesthetically similar pieces of art, predominantly featuring imagery of the grotesque and the exotic. However, while stylistically similar, Ensor and Nolde’s artworks do not necessarily have the same meanings and interpretations. This paper will discuss the possible interpretations of Ensor’s and Nolde’s artworks, and how these two artists exemplify the risks of oversimplification caused by grouping artists by movement, such as Expressionism. It will argue that Expressionist art does not have a standardized formula for understanding certain imagery, such as the grotesque and the exotic. Despite visual and stylistic similarities, James Ensor and Emil Nolde might have had vastly different intentions behind producing images of masked figures, grotesque faces, and non-European imagery. In order to determine and better understand the interpretations behind Ensor’s and Nolde’s artworks, and thus explain why art movements can be limiting, this paper will address both of the artists’ biographical information, primarily focusing on their political affiliations and opinions regarding the social hierarchies of their time, and how these factors may have contributed to their artistic choices. It will also examine the historical contexts in which the artists were working, discussing how this might have influenced their works. Additionally, this paper will examine multiple artworks of each artist, in order to compare and contrast their potential motives in creating certain aesthetically similar works. Through this comparison, this paper seeks to better comprehend Expressionist art as a whole: can it be assumed that an Expressionist image of the grotesque/exotic has one essential interpretation, or does the interpretation vary on the artists’ own experiences and beliefs? This paper concludes that, through examining the artwork of Ensor and Nolde, the latter holds true. Although Expressionist artworks may be similar from a visual stance, the interpretations are entirely subjective and relate heavily to the beliefs, histories, and affiliations of the individual artists.