Founded as Educational Comics in 1944 and rebranding itself as Entertaining Comics a few years later, EC Comics would publish several comic book titles, such as Tales from the Crypt, and the magazine, Mad. While the success of these publications can be measured by a legacy of directors, writers, comedians, and others in the entertainment industry who describe EC's properties as an early inspiration for them, the company itself cannot be seen as equally successful in the business world. Though its publications have left permanent fingerprints on American popular culture, the company represents an interesting example of a company that never became 'big.' In short, EC provides an interesting contrast to standard narratives about entertainment companies and properties. With scholarship in this field typically analyzing how a company started off small and grew into a larger corporation, EC is an example of a company that started small and remained small as a subsidiary of a larger corporation. In addition to this dissertation functioning as a critical corporate biography of EC's evolution, it also examines how U.S. entertainment has changed as mass audiences have become increasingly fractured as new forms of entertainment technologies have emerged. Overall, this dissertation aims to show how standard humanities approaches to analyzing popular culture can be augmented by also investigating the business practices and work cultures that shaped an entertainment property.