When displayed in museums and classrooms, Renaissance-era (1420-1600) painting, architecture, and drawing masterworks are often decontextualized from the social reality of the Academy system under which they were produced. For centuries, the artworks of the Italian Renaissance have seduced viewers with technical mastery, exquisite pigments, and engaging narratives, yet reveal little to non-experts about the cultural context of their production. Contemporary research methodologies and critical thinking, however, can help to deepen one's understanding of the art of the Renaissance period. Through dialogue, content analysis, and digital-based research, one can form more complete stories behind visual artworks that helped to shape a rebirth of Western culture. In this article, the author presents a small portrait of the Academy with ideas for artmaking or critical culture-based dialogue. The Academy system may be perceived as outmoded, but captivating cultural histories of the apprenticeship systems, artists' philosophies, and workshop rivalries enliven the period. Often, the story behind the art is hidden behind the art itself. The art object reveals an aesthetic and a somewhat understandable narrative, but the social context of production is a story the layers of glaze and the gilded frames cannot tell. For art educators who seek to better integrate inherited traditions in the visual arts into art education, the best method may be 21st-century thinking applied to 16th-century worlds. (Contains 1 figure and 4 endnotes.)