Something in the middle of nowhere. Little farm bank where they get all that USDA money. The four to five million cash that comes twice a year. Farm subsidy money.
In The Lookout, directed and written by Scott Frank (screenwriter of Out of Sight and Get Shorty), Gary Spargo (Matthew Goode) is the devil's advocate, a shady character, in appearance a formulaic plain thug, but some brilliant philosophical conclusions often burst forth from him whenever he's confronted with our bank nighttime clerk protagonist, Chris Pratt (Joseph Gordon-Levitt). Pratt is afflicted with a frontal lobe malfunction of his brain after surviving an accident four years ago when he was a hockey hero in his native small town of Noel, Kansas.
Chris walks funny and doesn't get along well with his estranged parents who don't visit his place (Bruce McGill and Alberta Watson), and his only friend is a blind man Lewis (Jeff Daniels), who works for a flower shop online. Lewis helps Chris to organize his messed-up sequencing of daily tasks as if it was an important story he must follow, listing such banal events as taking a shower, turning off the alarm, or cooking, creating a sense of order.
Chris is encouraged by Lewis to make small progress despite his terrible condition, so much so that Chris even tries to convince his boss Mr. Tuttle (David Huband) that he could be a competent teller at The Noel State Bank & Trust. If given a chance, he could be as friendly and accurate as Mrs. Lange (Alex Borstein) who "is never out of balance". But after attending a Thanksgiving day celebration in his parents' home, the tension between them refloats his internal bitterness again: "Never come back home," Lewis warns him.
His interactions with women are also frustrating; the scene he describes to his caseworker Jane (Carla Gugino) is an embarrassing proof of it; his social skills are weak, although some are friendly to him, like Deputy "Donut" Ted Tillman (Sergio di Zio), who jokes with Chris and whose wife is pregnant; he's the archetypal affable character we can find in classical noir cinema.
So when Gary – who suffers from anhelation breathing – chats Chris up about a risky business which he's been planning, this reactivates Chris' hidden desire to become a winnner for second time ("The Mustangs are the new state champions!"). Of course meeting ex-stripper, asthmatic Gary's collaborator and ditzy femme-fatale Luvlee Lemons (Isla Fisher), blinds him eventually after a seduction game so long needed by our sexually tormented ex-athlete. But for Lewis, this new redheaded female companion isn't good news – he makes a sleuthing report of her perfume, her "performer" vocation, and intentions for good measure.
Gary's message ("whoever has the money has the power" or quoting Amber Pawlik, "money is the cure to all evil") is almost the only honest thing that resonates in Chris' ears these days, and his father isn't disposed to lend him money for the moment. Chris is unable to forgive himself for the maiming of his ex-girlfriend Kelly (Laura Vandervoort) in the accident that left him brain-damaged, and in a dream she says to him she’s no longer mad at him.
The plot is divided in a third act of heist and gunfires, but especially in the moral order that Chris must pass through, where he will have to be saved or killed. "The simple truth is, Chris you're smart enough, you can get away with anything, including murder," is like an echo of that new brand convertible crashed into a truck because of Chris' negligence.
The film's metaphor could be more complex we'd suppose, the opposite stages of Chris as the high school victor, admired and envied (by Gary and Luvlee among them), and the lonely has-been, angry victim he's become. In Amber Pawlik's words: "Despite popular belief, evil is not the product of people who feel confident in their ability to negotiate reality. Evil has always been the product of have-nots. […] Indeed, I am looking forward to the movie that actually captures evil for what it is. A movie in which the antagonist is not the ultra-intelligent Ph.D, but rather the person who has slipped into the evils of victimology."
And of better days
From this town, we'd escape
If we holler loud and make our way
We'd all live one big holiday.
(From "One Big Holiday" by My Morning Jacket, from the film's opening sequence.)