[90 degrees west]
St. Louis

See also Rockwell Gray's excellent essay, "History Lessons".
I hope to eventually add my own opinions here, but Rockwell has the advantage of being, first, an outsider, and second, a much better writer than I: which means that he can better see St. Louis as a single entity, and that he can impart the idea of that to the reader much more accurately.
Suffice to say that I am from St. Louis, and that I continue to hold the opinion that it is much better than most other places.
There is a very interesting website here that discusses the architecture of St. Louis. (The protograph above was shamelessly stolen from that site.) Of particular interest, to me, are the sections on St. Louis landmarks that have been torn down or that are being allowed to fall down. At the turn of the 20th century, St. Louis was a much more important place than it is today; it was the third largest city in the United States, and industry was booming. Quite a few fantastic early skyscrapers (among other things) were built, and the world's busiest train station (shed visible in the above photo) was in operation.
Well, the train station is now a struggling tourist-trap mall (there's a column about it here from the St. Louis Post-Dispatch), Amtrak having moved to a "temporary" station made of bolted-together trailers in 1978. And a good number of the old buildings have been demolished and replaced with glass boxes (usually with less rentable space than the buildings they replaced), parking garages, windswept plazas with nowhere to sit, etc.
For a city so hung up on its history (people still talk about the 1904 world's fair!), St. Louis is almost incredibly hostile toward its physical heritage. With a large industrial base, St. Louis was hit hard by the white flight to the suburbs of the 1950s and 1960s. In the 1980s, the city adopted the policy of tearing down and/or securely boarding up abandoned buildings. A lot of the boarded-up buildings catch on fire with alarming regularity, and are then torn down. When you fly into St. Louis today, you can see the results of this: large sections of the city look like a grid of parks, with buildings scattered here and there. These are formerly-healthy blocks that have been almost completely demolished and carted away.
Consider for a moment that the building pictured at right (photo also stolen; you really should go visit that page, which has a lot more photos and the most comprehensive history of this building that I've seen) sits in a major city in the richest country in the world in the middle of boom times for the U.S. and St. Louis. It has been left empty and allowed to deteriorate for nearly thirty years now. It's a three-block walk from a metro station, four blocks from an Interstate highway, and about five minutes' walk -- literally five minutes -- from St. Louis University, a large theatre, restaurants, the St. Louis Symphony Orchestra, etc.
It's possible in St. Louis to drive down wide avenues lined with actual mansions, all of which are boarded up and/or falling down. This would be bad enough in any city, but it's especially disheartening in St. Louis. Because of an accident of geography -- St. Louis sits roughly at the confluence of the Missouri and Mississippi rivers, but it's very nearly in the center of the United States (Kansas City is actually closer), and it's just a few miles west of being at 90 degrees west longitude, or the exact middle of the western hemisphere -- St. Louis was for a long time the jumping-off point for the West.
As a result, the city has a unique combination of attributes. It's built on a Western scale -- the streets are (too) wide, the lots and houses are large, etc. - but with largely east-coast-style architecure, with a definitely detectable French accent.
Chicago enjoys similar circumstances and a lot of the same results, but Chicago doesn't have anything like the history St. Louis does. Between the Fire and the incredibly rapid growth of the city around the turn of the century, large parts of Chicago have that depressing blandness that you get when entire neighborhoods are constructed at the same time.
It's a shame that the St. Louis "city fathers" -- an actual formal group there, known as Civic Progress, Inc. -- don't have the good sense or long planning horizon to preserve what they've got. St. Louis seems to think that its future is in tearing everything down and replacing it with something blander. I haven't known that to succeed yet.
