Caravaggio’s paintings are to a great extent vexing, ambiguous and provocative. They deviate from traditional visual patterns, subvert conventions of representation, and push the boundaries of what is worthy of painting by expanding the range of the genre. How can we explain the overtly calculated breaches of the principles of appropriateness and the clarity of depiction at a time when, in a quite unprecedented manner, religious pictorial imagery was being standardized and brought into line with the ideas of Catholic reform? This is the question addressed in this study, which outlines a model for describing the changes in painting around 1600.