The actual heist is merely a backdrop for the internal monsters that plague the protagonist. This makes for an amazing story.
The good thing about critically acclaimed box office failures is that they all get a second chance. So even if mis-marketing or lack of mainstream appeal might have been a film's downfall, there's always a new life waiting in the DVD market. It happened with Fight Club. It happened with Serenity. Hopefully, it'll happen with The Lookout, one of the best movies of the year.
As far as The Lookout's dismal box office performance, marketing was probably the main culprit. After all, audiences were getting tired of the "ultra cool heist flick" and judging by the trailers and promos, The Lookout looked like just another carbon copy in this genre. Even the DVD cover has the three leads standing side-by-side, looking like they're about to kick some major butt with the tag line, "Whoever has the money, has the power."
The Lookout is actually less of a heist flick and more of an involved character study. The actual heist is merely a backdrop for the internal monsters that plague the protagonist. There's less emphasis on flash and style, and more on simply telling an amazing story.
After a car crash left him with a severe head injury, Chris Pratt (Joseph Gordon-Levitt) has to struggle through life knowing he's no longer the person he was. Simple things like preparing coffee or reading the newspaper confuse him and he struggles daily with his memory. A once successful hockey player, he now spends his time mopping the floors at a bank as he daydreams about life before the crash.
Suddenly, in comes Gary Spargo (Matthew Goode) who seems to fill the void missing in Chris' life. Gary, and the help of braindead ex-stripper Luvlee (Isla Fisher), manipulate the lonely, impressionable Chris and convince him to take part in a heist. Chris is apprehensive at first, but soon sees it as an opportunity to rebel against his current self and to get a small grasp on his past self.
Now, before anyone mentions similarities with Memento, the topic of head injury is all the two movies have in common. While Memento was an exciting, stylish workout for the audience, The Lookout is less preoccupied with being cutting-edge, and instead thrives on simplicity. With such an impressive script and well-written characters, there's not much else the film needs.
Simply following Chris as he narrates his day ("I wake up, I take a shower with soap, I don't read the paper,") is enough to pull us in. We experience the subtle changes in him and empathize when he stumbles and makes mistakes. Chris is the quintessential anti-hero. Even in his finest moments he tends to somehow screw it up, but his flaws make it easy for the audience to connect with him, making Chris a character to root for.
A true surprise was Jeff Daniels as Chris' blind roommate, Lewis. Daniels effortlessly takes control of every scene and drops one-liners like he was born to do it. Although at first Lewis seems to only serve as a light comic relief, he also looks out for Chris and is the wisest and most likable of the characters. In a scene where Chris tells Lewis how hard it is to simply sequence his day, Lewis tells him to start at the end and work up; "You can't tell a story if you don't know where it's going," Lewis says, which becomes a recurrent theme throughout the film.
Goode, who's mostly known for starring in Woody Allen's Match Point is also convincing as "the bad guy" Gary, so much so that, like Chris, even the audience begins to believe his charming facade. The scene where Gary and Chris meet for the first time in a bar is one of the highlights of the film. Gary's casual attitude and Chris' desperation for social interaction is interesting to watch unfold.
Fisher's portrayal of Luvlee, the ex-stripper who uses her sex appeal to lure Chris into the heist, goes against being the typical femme fatale and instead is more wide-eyed and naive. In the commentary, director Scott Frank remarks that he's still not entirely sure if he agrees with Fisher's portrayal, but it does make her character slightly more likable. Her dim-wittedness could have been turned down a notch.
The bonus features are typical, except the content is heavily slanted to the business side of film. In other words, it contains all those film technicalities that would drive a film student nuts. Although the mini featurette "Behind the Mind of Chris Pratt" delves a bit into the characters with an interview with Gordon-Levitt, the rest of it is mostly about how hard it was to film on location, how certain scenes were filmed in studios, the type of cameras used, etc. Of course, none of it is pointless information; it's informative for those interested in the technical side of film.
In a way, The Lookout's failure at the box office is actually a good thing. Many years from now it might be considered one of the greats, sandwiched inbetween other cult favorites that also got a second chance.