Toronto's skyline is pretty epic for sure. If I had it my way, I would have no CN Tower in the mix, and the office towers a little more to the north. It would be my favourite hands down, and one of my top 5 in the world.While Toronto added a lot of density to it's skyline over the last decade, that density unfortunately covered up a few iconic elements to the skyline: the Royal York hotel, and the five distinctly designed (and coloured) bank buildings. Nonetheless, it remains the most iconic skyline in Canada and among the most iconic in the world (as can be seen over at UrbanToronto.ca: http://urbantoronto.ca/forum/threads/toronto-skyline.8967/page-121#post-1250476)
Calgary's skyline is great (2nd place, in my view), but the Bow Tower does give it a bit of a lopsided look, sitting off on the eastern side. The Bow also doesn't have a particularly elegant profile.