I have to say I still disagree with Empire's list. The reason why I rank Calgary as Canada's 2nd best, is because of the hieght of the buildings in the core, their design which taken all together I prefer over Montreal's or Vancouver's most distinctive buildings (by distinctive I mean height wise) and because of their placement in relation to one another. I trend prefer skylines with peaks i.e Toronto & Calgary as opposed to plateau skylines Vancouver(Shangri-la is not enough to break this effect) & Montreal(while the cities tallest are separated by gaps they still form a plateau effect since they are almost the same height).
But that's just my personal preference.
At the same time I respect his opinion and eveyone else's who says Vancouver's or Montreal's skyline is ahead of Calgary's.
A little friendly debating is fine, but there are really no wrong answers to this question.
Also, by no means am I suggesting that Vancouver's or Montreal's skylines are ugly or weak or flawed. To the contrary I think they are all very distinct and impressive and as Canadians we should be proud of our cities. For instance I'm very interested in seeing renders of the next 500ft+ buildings being proposed for Vancouver or Montreal. Where as I could hardly care less about some super tall going up half way across the planet. Canada is just where my heart is at.