Yellow, when I look at the comparisons you posted I think it helps prove why Sao Paulo's skyline is NOT the most massive. You are asking me to be in awe of a bunch of buildings that would barely even register in Shanghai or NYC, and are pretty much dwarfed by much of Tokyo, etc. It's all about the scale of it. When you throw up a 1600 foot building, suddenly everything else looks a little smaller. The buildings Sao Paulo is making its bones on are the types of buildings that you would gloss over as a "lull" in the main skylines of the other cities. When I see NYC I am not pointing out all the apartment buildings between and outside of Midtown and Downtown as the "impressive part of the skyline", yet most of those are still a larger scale than Sao Paulo! Let's throw a Pudong-sized area in the middle of Sao Paulo and then tell me how big the rest of the skyline looks then?
However, that is not to say it isn't massive, or massively impressive in scale. Obviously it is. But, if you take were to take Sao Paulo's tallest building and put it in one of the other cities mentioned... it would be ranked approximately in the low 50's in Tokyo, somewhere in the 60's in Shanghai, 70's in Hong Kong, and wouldn't even crack New York's top 120. In other words it wouldn't even register. Chicago has 4 buildings that are over DOUBLE the height to the roof. I think the lack of scale really works in Sao Paulo's favor for looking more massive, but if you ask me it's probably around 5th and dropping.
And that's my rant of the day