As a social figure, the tramp held significant prominence in 19th and 20th-century Western culture, appearing in literature, vaudeville, and early cinema, notably exemplified by Charlie Chaplin’s iconic “The Tramp.” Similar to discourses surrounding other modern social figures like the flaneur, prostitute, and hysteric, early discussions on the tramp emerged from socioeconomic shifts, technological and institutional developments, and power structures resulting from industrialization and modernization. Initially perceived as deviant and criminal, tramps were linked to economic turmoil and labor disputes, often depicted through a flaneur’s lens as lazy, drunk, and frequently of foreign origin. However, by the early 20th century, there was a shift in the portrayal of tramps, with some romanticized depictions highlighting their lifestyle as a symbol of freedom and adventure, as exemplified by Chaplin’s tramp.This paper explores the resonance of these urban discourses and representations of tramps in 20th-century Egyptian cinema, first in Egypt’s “first wave” of cinema in the 1920s and 1930s, second, in Egypt’s first “realist” wave in the 1950s, and finally in Egypt’s “new realist” wave in the 1980s. Initially, I examine two comedy films—Egypt’s “first” silent film, Barhum Looks for a Job (Muhammad Bayumi, 1923), and the early talkie, Everything is Fine (Niyazi Mustafa, 1937)—both reflect global sentiments of the (roaring) 1920s and the following Great Depression, as well as local nationalist and anti-colonial politics following the 1919 Revolution and Egypt’s semi-independence from British rule. Subsequently, I analyze shifts in tone following the 1952 Revolution, as seen in films like Cairo Station (Youssef Chahine, 1958) and The Tramps (Dawud Abd al-Sayyid, 1985). Here, the tramp is no longer a deviant, criminal threat to bourgeois morality (as he was in the 19th century) nor a romantic, adventurous, and comedic figure (as illustrated in early 20th century), at least alone; he now evolves to embody revolutionary sentiments and critiques within a neorealist urban setting, representing themes of social mobility and class dynamics. In that light, I view the tramp as a transnational anti-hero of urban modernity, contrasting with the bourgeois flaneur, and explore their depiction in relation to class, gender, and sexuality. Thus, I examine Egyptian tramps, old and new, as reflections of shifting social realities across different eras and genres of cinema.