Giorgio De Chirico definitely stands out as a peculiar character of the Italian Novecento and his art ties directly with Nietzsche's philosophy whose eternal questions paved the way to his "immanent meta-physics" which is typified and pervaded by ever-present melancholia brought about by a heightened awareness of the death of God. Grappling with "the world seen for the first time" De Chirico's narrative does not depict reality rather its ghost, the latter is seen by dint of revelations and hallucinations. This paper sheds light onto some significant kinships between the two characters as not only philosophical concerns are vital but illness too. The philosopher suffered since his very childhood from severe migraine and then from a psychiatric illness with depression while the painter unknowingly suffered from migraine aura. This ailment, affecting the fragile border amid perceived reality and hallucinated reality, turned out to be a remarkable source of inspiration which boosted the visions and the enigmas the artist was entwined with. Overall, Nietzsche ushered in a picture of the world that De Chirico has wholeheartedly shared, however, in the light of his disorder, the empathy went even further, and this is the noteworthy aspect this paper aims at underscoring.