This film’s trailers make it look like a man (Ben Stiller) who has a crush on his coworker Cheryl (Kristen Wiig) has to overcome his crushing reliance on daydreams to save himself. And, yeah, the film is kinda about that. But it’s also about the ruthlessness of corporate America, about the magic of the photographic image, and about the most unlikely friendship in movie history.
Walter’s job is Negative Asset Manager. In other words, he keeps track of the millions of photos that come into Life magazine, photos that were the bread and butter of that now defunct organization. The “transition” is managed by a world-class douche (Adam Scott) who doesn’t really even understand what the magazine is about, but is nonetheless single-minded in his pursuit of one picture: #25. The picture in question was one shot by legendary photographer Sean O’Connell (Sean Penn), which O’Connell tells the magazine should be on the final cover. O’Connell sent the picture to Walter, but Walter can’t find it.
To save the day, Walter goes on a quest to find O’Connell and, hopefully, retrieve #25. This takes him to some crazy locations where he interacts with a wide variety of interesting characters. It’s at this point in the film when reality starts to become more fun than the fantasy sequences that dot the film in the first act.
The blossoming romance between Walter and Cheryl plays in fits and starts, but remains sweet throughout.
But the most fascinating relationship in the film is between Walter and O’Connell. In a world where Walter is the equivalent of “a gray piece of paper”, the one person who really appreciates and respects him is O’Connell, essentially the coolest guy on the planet. No, really. Photographing an erupting volcano while strapped onto a flying biplane cool. All of the other relationships–his battle of wills with the corporate restructuring guy, the strained relationship with his family, the tentative romance with Cheryl–all of these, in some sense, play second fiddle to the bond between Walter and O’Connell. The way that plays out is extraordinary.
All in all, I really loved this movie.