The Simpsons Drama Festival was founded in 1946 by Ken Watts – an actor and children's radio personality.

Watts had been hired to help with youth promotions by Simpson's, where he met and subsequently married Ann Abbott. Abbott became business manager for the Simpsons-sponsored festival. Sears inherited the festival when it bought the store chain in 1980.

The festival began with three Toronto schools and expanded rapidly. It had tripled in size by 1954 and by 1956 it included 12 of Toronto DSB's 17 high schools plus 14 from what is now the GTA. By its 50th anniversary in 1996, participants numbered 7,000. Today, over 10,000 students compete annually from nearly 400 schools from accross the province.