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Definitely Rochester, Minnesota. It has a big downtown (area wise) and has buildings taller than most cities twice or three times its size. It has a population of 110,000 and a metro population of 190,000 and has buildings well over 300 feet, with the tallest being around 350 feet.
Also, Des Moines. Golden Valley and St. Louis Park MN have a shared skyline that is decent, but it is also only a few miles west of Downtown Minneapolis.
(in no particular order except for Chicago because i live there) My top skylines based on population are:
1. Chicago
2. Denver
3. Atlanta
4. Miami
5. Seattle
6. Minneapolis
7. Pittsburgh
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