The following essay provides a close reading of Pieter Bruegel the Elder’s painting The Misanthrope [Fig. 14.1] from 1568. The large-format picture is part of his late work and was paint only one year before his death. The theology of that time forms the context of my interpretation. In particular, Sebastian Franck’s writing Paradoxa from 1534 is my point of reference for the interpretation of the Naples painting. The German theologian was one of the most popular authors of the time in the Netherlands. H. Bonger and A.J. Gelderblom, looking at the research, note that between 1558 and 1621 translations of seventeen major and minor writings of the theologian were made, more than of Luther or Calvin. Franck’s spiritualistic thinking was of the greatest influence.1 So within the framework of existing research, reference was made to this source early on and almost all the texts of the German theologian’s were available for Bruegel in Dutch translation from the middle of the 16th century onwards. The concept of scepticism serves me in two ways to specify my interpretive project. Firstly, it denotes doubt about the cognitive performance of seeing and enables a self-reflection of the medium of the image. Secondly, it helps us to focus on a hermeneutic practice that is co-determined by doubt insofar as Bruegel’s pictorial programmes can contain hidden critical commentaries in relation to the Catholic Church.