This research is about approaching bossa nova from intra- and extramusical perspectives aiming to create interdisciplinary discussions about music. I analyze the Brazilian music genre as a social phenomenon raising hypotheses from various frameworks (race, class, identity, politics, US American imperialism, and culture appropriation) to support a linguistic study about content lost in translation in both music notation and music performance. I compare celebrated versions of Antonio Carlos Jobim’s composition Chega de Saudade (charts from U.S. Fakebooks,  a chart from Brazilian Songbook, and my transcription of Joao Gilberto’s version of the song) to highlight the ways in which U.S. Jazz musicians mistranscribed, mistranslated, and erased the Brazilian “accent”/groove as they proliferated Jobim’s work through recordings and Fakebooks. Ultimately, I discuss how these musicians failed to capture the underlying Afro-Brazilian essence of the genre and misrepresented the tradition, with lasting consequences on how much of the non-Brazilian world still hears and plays bossa nova today.