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I absolutely believe something like that can. The Dark Knight and the Transformers movie are well known to have been shot here. But I'm not convinced yet we've experienced enough recent films that sell our city very well. Like I said in a previous post, there's very little in these particular films that would have changed if you used NYC or Toronto instead of Chicago. We need neighborhood name drops and significant screen times in those neighborhoods. We need locally loved restaurants in commanding scenes. We need movie characters to explicity talk about the uniqueness of Chicago.
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I believe this will come out more as Chicago just has more film infrastructure. LA and New York are in so many movies because they have everything you need in abundance. An indie director can find camera men, grips, etc much more easily. Films with a lesser budget don't have to pay premiums for equipment, and so on. We have many people who want to film here. Joe Swanberg is a native and he tries to film his movies in Chicago and actually use it. For instance, the film Drinking Buddies used neighborhood names, the main characters worked at Revolution, and they took a trip to Michigan (St. Joe's if I'm not mistaken.) As the industry builds up you will get more films like this, films that show the heart of the city.