The Lookout was written and directed by Scott Frank. It took ten years to get made and is a labor of love... and a big piece of crap. Two thumbs down from Ngoc and me.
It's set in Kansas City. Why? According to Frank, "I spent time there, but mostly what I loved was that there was an urban environment right next to a rural environment and they're very close together. He can live downtown but work two hours away in the middle of nowhere and I really liked that." That is true, if you drive two hours outside Kansas City you're in the sticks, or another city. So, the setting is very important obviously. Kansas City is like a character in the film, you might say. Of course, his observation applies to nearly every city in the country between the east and west coasts. Obviously Frank had a window seat on a cross country flight or maybe a just layover at Kansas City International. And the in-flight entertainment, I'm guessing, was Memento.
"I really didn't know why, but I just loved where it was. I loved that the mob was no longer there, that it was sort of a dying mob city and more of a "sons and sons of" place now. I just thought it was kind of interesting. I ended up doing a lot of research." Apparently meaning he watched lots of old movies with Kansas City in the title because Kansas City has a very high crime rate and most gangs there don't look much like the Lookout's.