It is recognised that Freud formulated his theory of ‘narcissistic personality’ through his psychopathography of Leonardo da Vinci and that psychoanalytic approaches to art practice have been much influenced by this text. Nevertheless, concerns can be raised as to the relationship between pathological analyses of creative practices and historical representations of the aesthetic. This chapter takes up this problematic by addressing the position that Freud holds in establishing Leonardo’s work as both compensatory and sublimatory with the focus on Freud’s presumptions regarding Leonardo’s infancy and his assertion that Leonardo’s paintings trace his attempt to re-create the ‘boy adored and desired’ by his mother. From this position, the incorporation of Freud’s analysis of Leonardo will be examined as well as the way in which certain psychoanalytic theorists have conceived analyses which promote a contrast between creative practices, casting that which is seen to derive from narcissistic investment as subordinate to that which is seen to derive from the sublimative ambitions of Oedipal resolution.