Brazil's 1964-1985 military regime served as one of the principle catalysts for the leftist counterculture movement, Tropicália, which gave way to a new class of músicas engajadas. Later, during the period of redemocratization that followed the dictatorship, musicians extended the morphed the art into new forms, particularly through the use of rock-and-roll. The sociopolitical musical criticism that was formerly cloaked under the censorship stylistically transformed itself into an open, blunt, and much louder movement. Standing at the head of this new period of músicas engajadas was Renato Russo, frontman and lyricist of the Brock band Legião Urbana. At the height of political turmoil following the abertura, Russo confessed in a 1989 interview, "Até bem pouco tempo atrás, a gente realmente acreditava que poderia mudar alguma coisa. Depois, percebemos que não ia dar mais para mudar, mas continuamos acreditando" (Assad 207). This contradictory sentiment of both hope and despair in regards to the future of Brazil is present in a number of the lyricist's works. An analysis of Russo's músicas engajadas reveals a pattern of oppositions in Russo's relationship with the political and social state of Brazil, all of which can be categorized under the topic of hope versus disillusionment: an imagined utopian Brazil versus a perceived, present dystopia; progress versus stagnancy; and ironic criticism versus sincere aspirations for the future of Brazil. These contradictions are in part due to Russo's conflict as both an insider and outsider of the Brazilian experience, being raised physically close to the source of political unrest, but otherwise considered an outlier in terms of education, social circle, sexual orientation, and musical taste. This work analyzes the duality of hope and disillusionment in Legião Urbana's oeuvre in order to explore Russo's path in both criticizing and identifying the continuous missteps within the Brazilian state, and inspiring a new generation to correct the errors plaguing Brazil since colonial times.