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Underpinned by the assumption that the city was crowded with black immigrants from the South in the 1920s, this essay makes use of Benjamin’s concept of the flâneur to explore how the characters in Jazz can be reinvented as flâneur, extending the original concept of the flâneur to the previously neglected groups of people, namely, the black immigrants. To that end, I scrutinize what Benjamin delineates about the concept of the flâneur in The Arcades Project, and how the previous studies by Wilson and Parsons extend it, wherein I elicit the points that even these studies are not pertinent to racial diversity such as African American. Subsequently, focusing on aspects interspersed throughout the novel, I investigate how the black characters in Jazz are reintroduced as the flâneur. This paper concludes with “going back to in place.” The City, which used to be an observer watching and predicting what would happen to the characters, admits its position as a mere onlooker whereas the characters, Violet and Joe, become as a moving observer with their own individuality to stroll and watch the City. This essay, ultimately, aims to situate Toni Morrison’s Jazz on the trajectory of literary figure of flâneur.