Monastic communities dominated the physical and intellectual landscapes of the Latin Middle Ages; the manuscript production, the musical, liturgical, architectural, and artistic enterprises of nuns and monks, as well as monastic influences in commerce, education, and politics were central to the culture. Since the revival of Benedictine monasticism in Europe in the mid-19th century, and the spread of new and reformed communities to the United States, scholars and their students have carried out studies of medieval monasticism in the light of these groups, especially those that consciously mirror the life and practices of distant times. What can be learned from comparative study of medieval communities and modern ones, especially when they followed the same rule of life? This paper demonstrates the ways in which a documentary film made in 2004 (Work and Pray: Living the Psalms with the Nuns of Regina Laudis) in conjunction with a (2007) bibliography by Antoinette Bosco of the foundress Mother Benedict (Vera Duss) can be of special use in the classroom, whether studying the Middle Ages, contemporary practice, or comparative monasticism. The same kinds of evidence that are crucial for the study of medieval communities can be found and engaged through these materials, sometimes in genres that demand somewhat different approaches, but that teach about both the old and the new.