With the exception of New York, which American city comes the closest to looking like this? (compare, Boston)
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Probably Miami. Chicago also has a good shot due to the Loop and large parts of the North side (though the highrises are far more collected together in Chicago). Los Angeles is increasingly becoming more and more like that with a lot of dense apartment buildings and multiple skylines and individual skyscrapers poking out randomly, but will probably always have some spreads of hills and/or historically protected bits of single family homes preventing that full spread.
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