Alphabetic letters are ubiquitous, multivalent, and largely ignored. Playful Letters reveals their important cultural contributions through Alphabetics—a new interpretive model for understanding artistic production that attends to the signifying interplay of the graphemic, phonemic, lexical, and material capacities of letters. A key period for examining this interplay is the century and a half after the invention of printing, with its unique media ecology of print, manuscript, sound, and image. Drawing on Shakespeare, anthropomorphic typography, figured letters, and Cyrillic pedagogy and politics, this book explores the ways in which alphabetic thinking and writing inform literature and the visual arts, and it develops reading strategies for the “letterature” that underwrites such cultural production. Playful Letters begins with early modern engagements with the alphabet and the human body—an intersection where letterature emerges with startling force. The linking of letters and typography with bodies produced a new kind of literacy. In turn, educational habits that shaped letter learning and writing permeated the interrelated practices of typography, orthography, and poetry. These mutually informing processes render visible the persistent crumbling of words into letters and their reconstitution into narrative, poetry, and image. In addition to providing a rich history of literary and artistic alphabetic interrogation in early modern Western Europe and Russia, Playful Letters contributes to the continuous story of how people use new technologies and media to reflect on older forms, including the alphabet itself.