This paper discusses the studies of Adolfo Casais Monteiro, Jorge de Sena and Eduardo Lourenço who are three central authors in Fernando Pessoa’s critical reception, and connect them through the issue of irony in his work. Pessoa was an expert practitioner of irony, which unfolds at different levels in his writing, going from the simple banter to the expression of a deeply dubious conscience. However, irony becomes fundamental to the understanding of Pessoa’s work when characterized as a certain way of conceiving the world (unsettled in all aspects by a radical ambivalence), and is inseparable from the ideas of mask, fragmented subjectivity and the dissolving of boundaries between reality and fiction.