The first photo is taken from the east side of Yonge St. looking west, just north of College.

The second really is ancient history as that entire intersection has changed. It looks like it’s taken from the north side of the Yonge and Dundas intersection, looking south. The World’s Biggest Jean Store, Jewellery Exchange, and Licks are all gone and Yonge Dundas Square now occupies their post. The Maritime Life tower would now be visible further south along Yonge St., at the corner of Queen. Just past the Licks, across what is now “Dundas Square” street, is the current home of the Hard Rock Cafe Toronto.

The third is a reverse angle of the first, taken from the same side of the street but facing north. The building just visible on the right edge of the frame is the Courtyard Marriott, which has a Second Cup in the corner closest to you.

The fourth is really tough. The leftmost skyscraper looks like the Scotia Plaza and the one on the right looks like Commerce Court. Given the two building’s relative location to each other, I think this was taken looking south. The very square and squat building at the left edge of the frame looks like part of the Bay Adelaide Centre, which was abandoned in 1991 before construction really even got underway. It’s now on again (as the end of the Wikipedia article states), so that view will soon no longer exist.

Thanks for the trip down memory lane!

You’re right that the B&W film and poor quality of the scan make these photos seem older than they actually are. A good film scan, on the other hand, can make very old photos seem like they were taken yesterday.