Creative manipulations of language have long been recognized as important aspects of second language development. Research has largely examined playful language within adult foreign language classrooms; however, less attention has been given to the pragmatic use of humor among adolescent multilingual learners of English. Drawing on oral interactional and interview data in racially, ethnically, and linguistically diverse high school English as a second language (ESL) classrooms in the United States, this article examines humor and playful talk in the translanguaging practices of adolescent multilingual Central African immigrant and refugee students whose common languages are French and English. Data are analyzed through discursive identity frameworks that view identities produced through interaction, through heteroglossic perspectives on language use and development, and through a raciolinguistic lens. Findings reveal that everyday comedic classroom interaction afforded students opportunities to negotiate macro-processes of social, racial, and economic marginalization in and outside of school, and fostered group cohesion and metalinguistic awareness. This article concludes by presenting pedagogical implications of valuing and harnessing student-generated humorous interaction for meaningful language and content learning.