I just ran some random stats through my skyline rater. Of the following cities, picked scientifically by my own choice, Toronto, Montreal, Vancouver, Calgary, Edmonton, Winnipeg, Quebec City, Ottawa, Hamilton, the worst skyline goes to:
Hamilton
It's not even close. Lack of height, lack of variance in heights, lack of anything architecturally interesting. Even with Ottawa's lack of height variance, having Place Export Canada, the Lithwick Building, and Parliament Centre Block save it from Hamilton's fate.