I also strongly agree with Jdot's post. Things take time. Many cities all over the world have a place like Times Square or Picadilly Circus, I've seen examples in Buenos Aires and Mexico City, and a long long time ago I remember seeing a hideous little ad covered building in Copenhagen - not sure if it's still there. No, Dundas Square is not Times Square, and it will never be. It will slowly improve, though, over time, and seem less like a rawness on the streetscape. I don't turn to ad covered buildings in Times Square for architecture, so whether or not TLS is architecturally significant is beside the point, I think.
Also, I think many posters look at everything European with an unrealistic eye. The centre of Paris is tourist and rich-Parisian land, from what I understand the suburbs are pretty dreadful. I have walked twice along the new waterfront in Amsterdam, some of it I like very much indeed, but some of it was absolutely appalling. The Dutch seem to have a fear of commercial activity, and right alongside an architecturally distinguished building, just outside a market and beside a tram stop, was a kind of tent-like apparatus, in what passed for a commercial zone, where someone was selling flowers. It was a complete failure of urban design:
Nice building!
What's this? (See lower left in upper photo).
Frankly, though I'm glad I went to Adam's waterfront, area, I won't be back. (That wasn't the only thing I didn't like about it). My point is not to slag Amsterdam, but merely to point out that the process of building a city is a long term and difficult one, full of hits and misses. I am certain that they might go back and fix some of their mistakes. But yes, they do make mistakes.
I do think that, in general, Europe gets it more right than we do, but the context of those cities in terms of the support for city building, their age and history, their land use policies, etc. is so different, that, unfortunately or not, we aren't going to have the same kinds of developments here.
What I object to is the tiresome kind of cherry picking from web cruisers that goes on. We're not Paris! Look at what Tokyo just built! What can't the Four Seasons be the Sydney Opera House? I have yet to visit a city where the majority of buildings are not banal everyday structures because that is, for better or for worse, what most cities are made of. You can stamp your little feet and demand Manolos all you want, and feel envious of what Marie over there has on her feet (even if they are causing her blisters), but it doesn't mean you are going to get them.