In truth, The Lookout's a rather straightforward narrative: A kid is riding high till he's brought low by a horrific accident that leaves him a shell of his former self. He spends years wrestling with pain and guilt but can make no headway thanks to the fact that his head's in the way; he can remember everything but keep nothing straight, not even his morning routine or where he keeps the can opener. His blind roommate (a bearded and bespectacled Jeff Daniels, looking strangely like The Dude) convinces him to treat his life as a short story, to write everything down in his notepad and to always begin at the end. "Can't tell a story if you don't know where it's going," says the roommate-turned-sage.
Scott Frank, however, begins at the beginning, with Chris Pratt (Joseph Gordon-Levitt) soaring at his highest, brightest moment: His wealthy old man (Bruce McGill) has just bought him a convertible sports car, which Chris drives into the dark, clear night accompanied by the ethereal Southern-rock strains of My Morning Jacket, his stunning blond girlfriend and another giggling couple. Chris kills the headlights, to woo and wow his girl with a sky full of fireflies. They laugh, sounding like every other high school jock and homecoming queen who believe themselves immortal—till their giggles are drowned out by the sound of crunched metal and shattered glass.
Years pass, and when next we see Chris he's in therapy, trying to piece together the fragments of his battered brain. He can't recall what he's done that very day. He makes grotesque overtures toward his forgiving caseworker (Carla Gugino, in a brief cameo). He thinks he sees out of the corner of his eye the old girlfriend, who, as far as the audience knows, might have been killed in the accident. He can't find the can opener, which his blind roommate can locate no problemo, bro. He's got a dead-end job sweeping up a small-town bank after hours. In short, he's trapped—by his guilt, by his injury, by the old man who gives him just enough dough to pay rent, by a bright future that turned into a shit present.
Which is why Chris, the least likely candidate for a bank heist, bites when a guy from high school named Gary (Matthew Goode) baits the hook. "Whoever has the money has the power," Gary tells him. "Don't you want your old life back?" Gary dangles extra incentive: Luvlee Lemons (Isla Fisher), a former stripper who, like Gary, was ahead of Chris in school but nonetheless in awe of him way back when. All they ask of Chris is that on the night of the heist, he act as—here it comes—the lookout.
There are moments when The Lookout feels like an early screenplay from a veteran writer; it has a few plot holes (involving a security system and a character who simply vanishes with no explanation), but when considered as a whole, when appreciated and absorbed from hypnotic start to thrilling finish, The Lookout works. It takes its time, saves its breath, lets us know these people before putting guns in their hands and tossing them in a tiny bank vault on a winter's night. Frank likes his story, but he loves his characters.
Gordon-Levitt, who was only beginning his stint on Third Rock From the Sun when Frank first wrote the script, was last seen on-screen swishing around in his mouth the tangy gumshoe slang of Rian Johnson's solid Brick. The Lookout is sort of Brick's flipside—noir filled with silences, a movie in which the hero's always this close to playing the patsy. As Chris, Gordon-Levitt has to play a kid who can't find the words to say what he means; the movie hints that for a long time he couldn't even talk. Gordon-Levitt's worth the admission all by his lonesome. He's that good—the proverbial young man with an old soul who brings unexpected depth, complexity and sincerity to what could have been just another damaged-guy role. He's the one to look out for.