The Freakonomics blog has a nice post about Chicago and New York duking it out back in the 1970’s for financial dominance.
The movie I, Robot, (very) loosely based on Isaac Asimov’s short stories, takes place in Chicago, in the year 2035. In the movie, the main new addition to the skyline is the US Robotics building. Here are a collection of photographs and charts exploring the architecture and skyline of Chicago from the movie. Attempts are made to place the new building in its setting (complete with a map of where the US Robotics building is located), as well as better understand the skyline design in general.
Awhile back, the Skyscraper Museum in New York City had an exhibit entitled BIG BUILDINGS. This exhibit, with an extensive online component, explored the history of really big buildings. Two categories, based on research, were created for these large structures, called Jumbos and Super Jumbos. These are buildings that are extreme, both in height and volume, relative to when they were built. Here is the Jumbo calculation methodology and here are the Jumbos and Super Jumbos built since 1950 (as of 1999, when the exhibit was held). Lots of good pictures and data for the skyscraper enthusiast.