This paper explores the relationship between transnational media and the dramatic increase in English language users and uses within Kachru’s (1990. World Englishes and applied linguistics. World Englishes 9(1). 3–20) Expanding Circle. Traditionally, English has been considered a Foreign Language in the third and demographically largest sphere of Kachru’s (1990. World Englishes and applied linguistics. World Englishes 9(1). 3–20) World Englishes framework. Yet in recent decades, the language has spread significantly within speech communities in e.g., continental Europe, South America, and the Middle East. In contemporary Expanding Circle contexts, English has gained international and local uses, for interactions with individuals from abroad and fellow speech community members. Thus, English has evolved beyond its single, traditional role to acquire the added functions of Lingua Franca and Additional Language. This study examines these changing roles in connection with transnational media’s development over the last century, given the leading industry position of L1-English Hollywood. The paper reviews the transnational history of cinematic film, television programming, and video streaming on-demand, with their evolving top-down language policies and bottom-up viewer practices. The European context of Germany illustrates how English use within these domains over time reflects changing proficiencies and roles for the language.