Blackboards were turned into tables … Questioning ‘horizontality’ in collaborative pedagogical art projects is research based on the practice of the collective microsillons, which is developing collaborative pedagogical art projects in different contexts. The aim of the research is to explore the possibilities offered by ‘horizontal pedagogical exchanges’ and to question the very notion of ‘horizontality’. It interrogates the possibility to challenge, through artistic projects in educational contexts, the traditional master–pupils (or artist–participants, or gallery educator–public) relationship. After a presentation of microsillons’ position in the cultural field, in particular regarding gallery education practices, collaborative art practices and the Educational Turn in Curating, a series of five collaborative pedagogical art projects realized by the collective between 2009 and 2011 are presented. Inspired by methods such as thick description and Participatory Action Research, situations in those projects are studied where a more horizontal pedagogical exchange is sought. Paulo Freire’s reflection about dialogical pedagogy serves as a starting point in this reflection. Anarchist and libertarian pedagogies, as well as the critical pedagogies discourses following Freire, are used to discuss the various strategies used by microsillons. Through those case studies are discussed the ideas of the classroom as a laboratory for democracy, of content co-generation, of network-like organization, of unpredictability and of constructive conflicts. Drawing from poststructuralist and feminist perspectives, key terms of critical pedagogy (such as empowerment) are then rethought and the idea of ‘horizontality’ questioned, complexified, presented as a utopian horizon rather than a practicable concept. Shortcomings and paradoxes in the projects’ attempts toward more egalitarian exchanges are identified and the limitations of the term are discussed. Thoughts about ways to overcome those reservations and to avoid romanticizing ‘horizontality’ are proposed, opening to microsillons’ future projects.