Frank Hallenbeck’s widely distributed picture of a congested Chicago intersectionIntersections in 1909 depicts the chaos of early 20th-century streets. The photo shows a space teeming with people, horses, vehicles of all sorts, streetcars, awnings, and signs—all poured into one streetscape. Cluttered, yes. But a lively, animated street scene, nevertheless. If we check Google’s current street view of this space, a more orderly but less fascinating world presents itself. The chaotic competition between vehicles, animals, and people has given way to an orderly succession of automobiles. Sixty-plus years of planning regulations have taken their toll on the street’s appearance and liveliness. This chapter explores the street’s evolution from a lively, cluttered streetscape into an efficient, uninteresting throughway. It examines subsequent attempts to regain some of the street’s earlier liveliness and assesses the impact of the Covid-19 pandemic on reclaiming parts of the street for outdoor activities. Now that life has almost returned to the pre-pandemic normal, many city officials are searching for ways to keep their cities economically viable and ward off or turn around their decline. By creating new housingHousing and bringing back diverse activities to enliven what had become a transitTransit corridor, they hope to attract residents and visitors to support the economy and thus help reinvigorate the city streets and their surrounding areas. This chapter questions whether the 15-min-city concept can be successfully applied or, as A.R. becomes more common, whether the future of the American urban street lies in its virtual augmentation instead.