An interesting field of psychopathology has been historically oriented towards identifying the links between artistic expression and psychological problems, searching the biographies of various artists for the deep psychological origins of their art. The painter Giorgio De Chirico has been the object of many studies and recently his documented suffering was diagnosed as problems with migraines and temporal epilepsy. However, a precise psychiatric diagnosis is still missing. The authors, using autobiographical and biographical resources, attempt to reconstruct the psychopathological medical history of the painter and subsequently classify the psychiatric diagnoses using the DSM-IV. With this methodology the authors proposed that the artist displayed a personality disorder with narcissistic and paranoid traits and had suffered from somatization disorder and adjustment disorders in three-year periods, from 1909-1911 and 1915-1918.