Abstract: Prior to the eve of the Great Depression in the 1930s, the portfolio of towering skyscraper renderings crafted by American architect Hugh Ferriss profoundly ignited the imagination and fervor of architects, urban planners, and the general public alike, envisioning the metropolises of tomorrow. This paper first delves into the rationale, underlying realities, and far-reaching implications of Ferriss’s depictions of skyscrapers and futuristic cities, along with his seminal work, The Metropolis of Tomorrow. Subsequently, it explores the diverse receptions according to Ferriss’s drawings across various eras, in particular the critiques levied by his contemporaries in the 1920s with reinterpretations and enduring influence on subsequent architects and urban theorists, notably Rem Koolhaas during the 1980s and 1990s.