Although Essanay Studios closed in 1918, the area’s reputation as an entertainment center continued. Among the splendid theaters which operated in the area were the Uptown (4816 N Broadway), the Riviera (4746 N Racine), the Lakeside (4730 N Sheridan), and the lavish Aragon Ballroom which opened in 1926 at 1106 W Lawrence Avenue. For nearly thirty years the Aragon featured Big Band music. Even after the popularity of ballroom dancing waned, the Aragon survived as a roller rink, then as a boxing and wrestling arena, a discotheque, and a gathering place for fans of rock and Latin American music. The Green Mill on the corner of Lawrence and Broadway is full of so many stories, including stories from Prohibition days, when gangsters and their women mixed in with other speakeasy clientele, dead-end stories of crime and revenge, purple stories of romance and fame, all jumbled together and allowed to gradually mellow and ferment.
The community was christened “Uptown” in the 1920s by Broadway and Wilson Avenue merchants who borrowed the name from the Uptown Store, a fashionable department store in the area.
This area became popular among young singles and married couples. Encouraged by the demand for living and commercial space in a prime city area, property owners converted older mansions, homes, three flats and six flats into smaller units and even kitchenettes. Basement apartments were converted into shops, and stores were built into the fronts of existing buildings.
The community's fortunes changed during the Great Depression. A resident at the time said “…residents ranged from the poor to the rich… but the poor were jobless… only because there were few jobs to be had. Most were educated to some degree, proud and ambitious, and they had hope coupled with strong family ties and discipline. People were able to cope with the Depression. Our mothers were culinary magicians in preparing good meals on a poor income. A member of the family would ask the friendly neighborhood grocer if he could have a couple of dollars worth of groceries ‘on the cuff’ until some money came in.”In addition to the Great Depression, the extension of Lake Shore Drive to Foster Avenue in 1933 made it possible for shoppers to bypass the Uptown/Argyle area for places further north.