I think it's necessary to evaluate a skyscraper at multiple scales, since that's how we experience it: from right next to it on the street to from across the river, as well as at all kinds of points in between. It's important to think of it as an element in a larger skyline, but also as an element in an immediate streetscape.
Right after 9/11 it looked as if the idea of a huge skyscraper might be considered obsolete. It came back, but I think that's more closely connected to the rise of Asian and Middle Eastern cities in the world economy (Dubai, Shanghai, Taipei, etc.) than anything else.
The bias among architecture critics isn't against skyscrapers per se, but against the way in which their design is so heavily dictated by economic considerations - the way in which skyscrapers are real estate before they are architecture.
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