In the latter part of the 19th century, immigrant German and Swedish workers settled in Roscoe Village, split between the industrial depots along the Chicago River at the western most point of the village, and the plants and factories on the eastern border. The post-war economic boom of the 1920s brought more development to the area with brick buildings springing up, often creating entire blocks of identical two-story brownstones lining the streets. Practically impossible to distinguish one building from another, some of Roscoe Village's residential blocks still maintain this Old World architectural charm.

Because much of the economy collapsed during the Great Depression, many of the warehouses and factories ceased operation, and their spaces went unoccupied. Still, the character and history of Roscoe Village remained, as colorful politicians such as 'Burgermeister' Charlie Weber wore lederhosen during parades as a way to keep residents upbeat and optimistic.

After the federal interstate highway initiative in the 1950s made travel between the suburbs and city that much easier, many villagers left the struggling community for the inexpensive homes and good schools of the suburban 'collar counties.' By the late 1970s, residential developers started to take notice of the locational advantages of Roscoe Village with its proximity to many other up-and-coming neighborhoods, and looked to the old industrial corridors for urban pioneering.

With the housing explosion of the 1980s, much of the industrial space had been converted into loft condominiums, including the conversion of the Eversharp Pencil Factory at Roscoe and Ravenswood, which because of its size (nearly a full city block) and history caught the attention of the entire city. All the new rehabs and additional restoration of walk-ups caused real estate values to shoot up as did property taxes, forcing much of the working class out and bringing a more affluent class in.