In the first half of the 20th century, the area now known as the Entertainment District was originally called the Garment District and was almost entirely industrial. With the rise of free trade and deindustrialization, industries began to leave the area in the 1970s. They left behind an array of historic warehouses and factories that were soon repurposed. The most notable new arrivals were nightclubs. In 1981, Toronto’s first large dance club, the Twilight Zone, opened in the area. Other clubs quickly followed, and by the 1990s, the area boasted one of the largest concentrations of nightclubs in North America. The railway lands to the south were also repurposed.

The SkyDome (now Rogers Centre) opened in 1989, drawing thousands of sports fans to the area. The CN Tower, which opened in 1976, also brought many tourists to the neighborhood. Along with the nightclubs, many bars and restaurants opened to cater to these crowds. In 1982, Roy Thomson Hall, home of the Toronto Symphony Orchestra, opened at King and Simcoe. The Mirvish family bought the historic Royal Alexandra Theatre in 1962, which proved to be a great success.

In 1993, they built the new 2000-seat Princess of Wales Theatre a block over. Independent theater companies also moved into the area, with Theatre Passe Muraille taking over a former warehouse and the Factory Theatre occupying a former manse. Toronto has since emerged as the world’s third-largest center for English-language theatre, behind only London’s West End and New York’s Broadway.