The New Yorker writer A. J. Liebling spent a year in Chicago in the early 1950s and wrote a three-part essay about the experience. The title of the book that followed from it, Second City, gave the city its nickname. It captured the urban rawness that poet Carl Sandburg had celebrated half a century earlier, but had a much less celebratory take on it, as in this famous passage:
Seen from the taxi, on the long ride in from the airport, the place looked slower, shabbier, and, in defiance of all chronology, older than New York. There was an outer-London dinginess to the streets; the low buildings, the industrial plants, and the railroad crossings at grade produced less the feeling of being in a great city than of riding through an endless succession of factory-town main streets. The transition to the Loop and its tall buildings was abrupt, like entering a walled city. I found it beguilingly medieval.
One of the angry responses to Second City was a postcard sent to Liebling that read, in full: "You were never in Chicago."
Here are images from that era in Chicago that Liebling captured so memorably in prose.