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? Scott Frank says, "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.
Note to Frank: If you'd googled "Kansas City" and "mafia," you'd have learned this:
Despite being in prison in 1995, Anthony “Tony Ripes” Civella was seen as the new crime boss. In 1992 he had been convicted of a scheme to divert pharmaceutical drugs from traditional sellers on to the gray market. He was convicted and sentenced to 4 years. Since 1996 he has been free and very active. The remaining Las Vegas interests fall under power of Kansas City LCN Family member Peter Ribaste. His underboss is William Cammisano, Jr. In 1997 all three were placed in Las Vegas’s Black Book and are barred from casinos in that area. Today the Kansas City LCN [la Cosa Nostra] Family is reported to have 20-30 “made” members and is a very tight knit group controlling many street-level rackets.