This article discusses strategies which Afro-Brazilian men used to distance themselves from demeaning assumptions and stereotypes attached to slavery and vagrancy in Rio de Janeiro. The piece focuses on the first 50 years after abolition (1888) but also shows how the ideologia da vadiagem—a set of ideas and stereotypes which defined black, poor, and mixed-race men and women as lazy and inferior—cast a long shadow deep into the twentieth century. The primary lens is the music market, which, beginning around the turn of the century, provided one of the earliest and most public venues in which black men were judged as members of a free society. Some musicians played samba and a number used malandragem, the lifestyle and ethos of flashy, masculine, malandro hustler figures, to cater to audience desires and also to distinguish themselves from caricatures of sickly, weak vadios (vagrants or idlers). Other artists rejected malandragem or only embraced it selectively, instead preferring a more toned-down “professional” look and demeanor meant to secure dignity and respect for themselves, their music, and the communities for which they served as figureheads. Eduardo das Neves, Moreno, Donga, Pixinguinha, Brancura, and Ismael Silva are among the musicians discussed here. By interpreting malandragem as a response to the ideologia da vadiagem, and as one of many identities and strategies employed by black entertainers, the article provides unique insights about the relationship between race, class, gender, and sexuality and a new way to understand the long-term effects of slavery and related assumptions about race and masculinity in Brazil.