Gangster Chicago, 1936

If there's anything that the movie Chicago taught us, it's that women's prisons routinely stage elaborate musical numbers. But if there's another thing that Chicago taught us, it's that the city of Chicago was a hustler's paradise in the first half of the 20th century.

The Sting definitely doubles down on that second point.

Almost all of this movie takes place in Chicago in 1936. From what we can tell, the entire town is run by a bunch of crooked politicians…and the private citizens aren't much more upstanding. That's why Luther Coleman tells Johnny to get to Chicago as quickly as possible if he wants to pull off a big con, saying,

LUTHER COLMAN: I got an old friend in Chicago named Henry Gondorff. I want you to look him up.

When Johnny finally finds Henry and asks him about his conman background, Henry explains how Chicago is "a rigged town." Henry knows that grifting is a business like any other in Chicago.

[…] owns a packinghouse, a few banks […] and half the politicians in New York and Chicago.

Could The Sting have been set in, say, San Francisco or Miami? Sure, but it might not have rung as true. Fictional depictions of The Windy City usually capitalize on its reputation for being corrupt and, since key plot points in The Sting involve a corrupt police force, corrupt politicians, and the idea of a corrupt Western Union…we're going to go ahead and say The City That Works was the right choice of location.