The work of Paulo Freire (1921–1997) is seen by many educators as topical and urgent to rethink pedagogy today. Furthermore, it inspires many contemporary artists through its use of visual materials. This article aims to investigate the various links – from different perspectives – between the work of the Brazilian pedagogue and art. In the first part, the text focuses on the images produced by artists especially for Freire’s literacy actions in Brazil in the 1960s and their use as illustrations of ‘generative themes’ in order to facilitate both literacy and critical consciousness [conscientização]. A second part of the text looks into the perception of art by Freire and into the way he identified several similarities between pedagogy and art. This allows to put his rather classical approach of art as a discipline into perspective with his writings that played a key role in the emergence of the notion of dialogue-based art and critical gallery education. Three examples of artistic practices (from Rollins + K.O.S., Ultra-Red, De Andrade) directly borrowing concepts and tools from the Freireian pedagogy are then presented. The article concludes by highlighting the way Freire’s writings have been called up in contemporary artistic spheres – in particular by critical gallery educators – and how it could be implemented in the field in future.