One of the staple components of "Sesame Street" over the last 50 years is the short, animated segments that periodically interrupt the narratives and focus on brief educational and literacy concepts. Histories of the show have recognized these segments and referred to them as commercials, but to date, literature lacks a comprehensive examination of the managerial forces involved in planning and producing these commercial segments to identify the depth of understanding Children's Television Workshop (CTW) possessed as they created this material. Even more intriguing, contemporary literature has identified conceptual overlaps between the components of successfully persuasive children's advertisements and successful strategies for teaching early childhood literacy. This study uses a historical analysis and primary evidence, from corporate and executives' personal archives, to identify and chronicle how CTW married literacy education and advertising to effectively "sell" literacy to child viewers of "Sesame Street." This study also identifies important implications and opportunities for research and the future promotion and presentation of educational concepts in contemporary digital media settings.