This chapter focuses on a comparative analyses of a series of chronicles, The Enchanting Soul of the Street, written by the writer and journalist João do Rio, and the short story 'The Art of Walking in Rio de Janeiro', written by Rubem Fonseca. There is no condemnatory or moralistic eye that judges looters, street people, prostitutes, evangelical preachers, or thugs in relation to a code of behavior. The stroller through the imploding streets of downtown Rio de Janeiro in the 1990s is experiencing a cultural demise that no longer relies on revealing the reversal of bourgeois decorum, notions of progress, and expectations of the ideal city. The chapter evokes the historical significance of downtown Rio in order to bring into the foreground the symbolic significance of the persistence of the past in a modern city.