I came across these photo from an old European-produced movie starring Brad Harris (left) and Tony Kendall (center). It's called "Kommissar X - Drei blaue Panther" and was shot in 1967 in Montreal as it was released in March 1968 in Italy. The photos are amazing. In the top photo the Montreal skyline is so different. I can spot Place Ville Marie, the Chateau Champlain Hotel (now a Marriott hotel) and of course the Sun Life building, which looks somehow different.
There are a few other building I know but there are a couple of them that I don't recognize. The building indicated with number 1 is totally unknown to me. It looks old and looks like it's supposed to be were the CIBC building is now. And then there's the building on the right, indicated with the number 2. Looks like an apartment building. I don't recognize it as well. It's beyond my time I guess. If anyone has any info on them, just write to me.
The photos below show how different the Montreal skyline looks different from a distance.