Deemed eccentric, El Greco's work presented a Greek path contrary to the one promoted in Vasari's history of art. His was an art that was sensual, complex, and difficult. Michael Damaskenos's profound engagement with Venetian painting was mixed with traditional iconic styles, reflecting life in a colony in which Orthodox and Catholic, Greek and Venetian were fluid rather than static descriptors of the self. Georgios Klontzas used his art to confront the horrors of his day. The impending threat of the Ottoman conquest of Crete and the outbreak of plague in 1592 shaped his extraordinary manuscript, Apocalypse and History, that sought to understand these calamities in light of both divine providence and human experience. Each of these artists chose an eccentric point of departure for their work. Greek, colonized, and fearful, they invite us to look again and to look differently at the later sixteenth century.