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This paper aims to approach cinema, philosophy, and pedagogy from a double Deleuzian perspective: from the work of the Portuguese filmmaker, Manoel de Oliveira, and from the philosophical praxis of Gilles Deleuze. According to Deleuze, there is a principle of affinity between the cinematographic and the philosophical form of thought expression, explored as a peculiar transversal project alongside pure philosophical inquiry. When Oliveira saw the public lecture that Deleuze gave in 1987 at La Fémis (“What is the creative act?”), he felt challenged by the philosopher’s words and wrote him a letter in 1991. Furthermore, Deleuze referred to the Portuguese filmmaker’s films as one of the “greatest pedagogies,” along with Roberto Rossellini, Marguerite Duras, or Jean-Luc Godard, for example. Cinema was then seen, for the first time, as a new (possible) cartography to the philosophical plane contributing to a mutually reciprocal movement between cinema and philosophy. In this sense, the encounters between cinema, philosophy, pedagogy, and thought as well as the connection between cinematic images and philosophical concepts, will be the theme of this essay.