This thesis presents an interweaving of the discourse surrounding Colin McCahon and Ralph Hotere, the philosophy of art, and Lacanian psychoanalysis. In so doing, a Lacanian understanding of subjectivity, painting, discourse, and their interrelationships is elaborated in order to generate some new perspectives on, specifically, the work of McCahon and Hotere, and related writing and testimony, and more generally, the practice of art history and art criticism in Aotearoa/New Zealand. In the first place, this project explains, develops, and applies a Lacanian model of subjectivity/meaning-making understood in terms of the figuring of desire. This formula models expressions of subjectivity/meaning-making in terms of the reciprocity obtaining between the agent-like, metaphoric precipitation and automatist, metonymic perpetuation of symptomatic formations or points de capiton in discourses of desire. Secondly, this study analyses the discourse comprising paintings by McCahon and Hotere, and related writing, from the perspective of two points de capiton – the key features of which are gathered under the rubrics ‘McCahon’s doubt’ and ‘Hotere’s reticence’. The thesis demonstrates that these two formations enliven the possibility of interpreting McCahon discourse and Hotere discourse, respectively, in terms of repeated and contradictory characterisations of McCahon as a visionary and a doubter, and of Hotere as eloquent and reticent. Furthermore, the thesis shows how, by virtue of their fixation on the symptomatic formations ‘McCahon’s doubt’ and ‘Hotere’s reticence’, respectively, McCahon and Hotere discourses bear witness to radically contingent affirmations of, or leaps of faith in, praxes of contradiction, thereby sustaining fantasies of the revelation of the reality and truth of the being and meaning of art subjects and art objects. The impossibility of objectively realising these fantasies testifies to the status of subjective desire as that which seeks only its own perpetuation or that finds fulfilment in endlessly missing its aim and, by the same token, in Lacanian terms, underscores the (structural and ethical) necessity of subjectively being in and as traversing fantasy.