To inhabit the city is to inhabit a layered and contentious space, a space whose meaning cannot be comprehended without closely navigating its layers. This article analyses two images and representations – a tweet and a song – as narrative forms that reveal the palimpsestic nature of Nairobi in the context of the city’s expressway, which was constructed between September 2020 and July 2022. I read the expressway as a physical infrastructure for mobility as well as a material and metaphorical representation of urban marginalization, which at the same time materializes various forms of social marginalization and exclusion that predate it. The narrative forms, critically analysed together, underscore the palimpsestic nature of the city that would otherwise be obscured should readers be blinded by the iconicity of the expressway. I consider both the images, the tweet and the song alongside the arguments of Michel de Certeau, Karin Barber and Setha Low on urban aesthetics. While de Certeau provides lenses through which we understand the practices of everyday life in the city, Barber makes a case for urban infrastructure and the growth of popular culture, and Low focuses on how power relations influence the social construction of space. Ultimately, I argue for a reading of urban spaces using a synthesized literary approach as a nuanced way of understanding such spaces. This approach weaves together different media and approaches – both textual and visual – in its reading of the materialities of urban spaces and how meaning is constructed and contested within those spaces.