When I was in my mid-20's, I dug out the old family 'etch-a-sketch' (google it) and could do the Toronto skyline at that time in about 10 minutes. I'd start with the CN Tower for height perspective on the screen, then move along to the Royal York Hotel (which you could still see in the classic Island postcard view - I intentionally did not include those lakeshore apartments or Westin because they were so hideous) then drop in the TWO towers of TD Centre, and behind it popped up FCP, then moving further east CCW and the classic CCN, the old Montreal Trust building, before moving just east to include the original Toronto 'skyscrapers: the little cluster at King & Yonge. It had that very pyramid feel, and was very easy to draw. I did it from my minds eye as I was such a skyscraper geek at that time. I hate to think of how hard it would be to draw today's skyline on the ole etch-a-sketch...much less 5-10 years from now!