Playhouse Square emerged in 1921-22 with the opening of the State, Ohio, Allen, Palace, and Hanna theaters near the intersection of Euclid Avenue and East Fourteenth Street. The brainchild of Joseph Laronge, four of the five theaters were interconnected. The largest theater, the Palace, was built to host B. F. Keith's vaudeville performances. In addition to vaudeville, the theater district featured plays, motion pictures, and eventually Cinerama films. By the end of 1969, however, all of the theaters but the Hanna had closed due to declining attendance.
The Junior League of Cleveland was instrumental in saving the theaters from demolition in the 1970s, forming the Playhouse Square Foundation and working with Cuyahoga County commissioners to restore and reopen the theaters. By the turn of the twenty-first century, all of the original theaters were again hosting performances, constituting the nation's second largest performing arts complex after New York's Lincoln Center. In addition to ticket sales, the Playhouse Square Foundation now maintains an extensive real estate portfolio stretching from the theater district to the suburbs, which supports ongoing preservation of the historic properties themselves while contributing to broader economic development.