| Summary: | Why were Caravaggio’s <i>Sleeping Cupid</i> (1608) and <i>The Seven Works of Mercy</i> (1607) requested for display at a number of humanitarian public events? And why did Caravaggio’s work inspire a series of photographic and journalistic reportages on contemporary migratory phenomena? This article surveys the main circumstances linking Caravaggio’s pictorial corpus to the so-called European migrant crisis. After critical reflection on the social construction of the “humanitarian Caravaggio,” the focus shifts onto a book that is at the same time a journalistic investigation of migratory phenomena, a literary work, and a theoretical reflection on the ways of looking: <i>La frontiera</i> (2015) by Alessandro Leogrande, which concludes with a reflection on the representation of suffering in Caravaggio’s <i>Martyrdom of St. Matthew</i> (1600). By following a path that connects Caravaggio’s painting, Susan Sontag’s thought, and Leogrande’s writing, what emerges is the critical and self-critical potentiality of a comparative approach to the arts and images.
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