Some old school Toronto 'shit'
...
CCN (1930)
The Royal York (1929)
Old City Hall (1899)
Canada Life (1931)
Optima Business Centre (1915)
Concourse Building (1928)
Whitney Block (1933)
Canadian Pacific (1911)
Traders Bank (1905)
There's a ton missing, but I can't find the pics as easily. You can find many of them on Emporis.
And to put in perspective, here's how it all looked like back then (all pics ~1930 +-5):
This one is a bit older:
And finally our greatest loss--the beautiful old Toronto Star building, replaced by the crappiest tall in the CBD, the First Canadian Place: