The monumental Crucifixion fresco in the Chapter room of the San Marco Monastery in Florence, Italy, provided the Observant Dominican friars who gathered there daily with powerful visual models for their communal religious life. Painted by the renowned friar-artist known as Fra Angelico c. 1441–42, this emotionally charged scene includes a retinue of grieving saints drawn from throughout Christian history, variously demonstrating their sorrow and contrition. In this video, we explore Angelico’s painting and learn about the community of sacred men and women who modeled their sorrows for the audience of Dominican friars. As the friars met, confessed their sins, and welcomed visitors beneath the image, its sacred figures offered models for how they themselves should live together.