Since this is exactly the way I remember the Gay as a kid, I would guess that this picture was taken in the very late 50's or early 60's. Hidden behind the streetcar would be French's Fish and Chips, known locally as Frenchie's, and a variety store, then beyond that were some row houses with no front yards. All these buildings have been torn down.
This picture was taken just before the Gay was demolished and replaced by townhouses. At the extreme left, which is the N.E. corner of Parliament and Dundas Streets, one of the three story apartment buildings in North Regent Park can be seen.
The Bluebell, later renamed the Gay theatre, stood at Parliament and Dundas right next to Cross's Esso service station. Even though it had been renovated, it didn't take long to once again become a dump. The floor was coated with gallons of spilled soda pop making it quite a challenge to walk between the seats without losing a shoe to the sticky floor.
The Saturday afternoon matinees could get so rowdy that there was actually a bouncer to throw out any kids that got out of hand.
But it was still very dear to my heart because this was my favorite neighborhood theatre. I spent many hours in this building watching monsters and cowboy heros like John Wayne parade across the torn silver screen.