The purpose of this essay is to pinpoint Damisch's theoretical perspective in his treatise on painterly expression and its "symptom". In his account of the historical turns in painting during the late 19th century to the early 20th century, Damisch raises the idea of a "symptom" at play. Hence pointing out that "symptom" does not equal features presented to the eye, nor does it possess an absolute definition. Instead, "symptom" stands for the very gap between modes of thought. Thus, Damisch outlines "symptom" through a series of dialectical inquiries, investigating its relation to certain theoretical concepts. In this essay, I will elaborate on the three investigations applied by Damisch, which are: (1)"What is at stake in the field of 'representation' of expression?" (2)"What is at stake in the field of 'form'?" (3) "What further development does this 'symptom' lead to?" It is shown that these investigations do not merely reinterpret the significance of the historical turn of painting during the late 19th century to the early 20th century, but also bring together the act of painting and that of discursive analysis, amplifying their resemblance.