In terms of sheer size and awe factor, I still say NYC is number 1.
Although, for sheer beauty Pittsburgh is really tough to beat, your driving through the mountains, emerge from a tunnel and there suddenly is downtown Pittsburgh. It's really cool!
I don't put much stock into those formulas that try to rank skylines by some linear combination of buidlings and heights - the fact of the matter is that places like Montreal and Vancouver would likely have much higher skylines than Calgary if they didn't have height moratoriums to protect the view of Mt. Royal and the mountains.
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