The problem with Calgary is the BOW.
It's an amazing building, don't get me wrong, but it's too bulky and in the wrong place.
My Favourite skylines are those following a bit of a pyramid or peak design.
The Calgary Tower should be more prominent yet it's being eclipsed by many new business towers in that area.
I'm going to be the odd guy out here and say that Vancouver looking south from lonsdale is my favourite skyline in Canada followed by the Toronto waterfront view you get from the Toronto Islands.
Notice the peak in the skyline around the shangri la and Trump Tower?
Vancouver's balance and density are it's saving grace. No mountains from this view, only the water front.