Recent discussions on English as an International Language have highlighted the important role played by English language popular culture for the identities and bilingual development of diverse global citizens who learn and use English. However, there has been little attention to connections between popular culture and "teacher" identity. In this article, based on life history interviews with Chilean English teachers, I draw on a Bakhtinian theoretical framework to illustrate similarities and differences between generations of teachers in their appropriation of English language popular culture. I examine discursive connections between these investments and their English teacher identities, outline teachers' perspectives on popular culture and English language pedagogies, and conclude by discussing the links between pedagogy, bilingual development, and English teacher identities in an era of globalization. (Contains 7 notes.)