The day after they invented cities, they invented stories about what happens when country bumpkins arrive in them. The adventures of the innocent in the big, bad metropolis have been popular for centuries. In part that is because of that satisfying moment when the fool from the country ends up outsmarting the sophisticates from the city, the ones who think he is an easy mark. First, though, he has to identify which ones they are. And then he has to identify who he is, and recognize his own strength.

Tim Lippe (“The Office’s” Ed Helms) has spent his life in a tiny Wisconsin town, and almost all of his life working in the small local office of an insurance company. He started working there at age 16. He does not even let himself dream of the success and cosmopolitan elan of Roger Lemke (Thomas Lennon), the office star, who always brings home the coveted Two Diamond top award from the trade association’s annual meeting; he just sincerely wishes him well. But then Roger dies suddenly, and Tim has to take his place at the convention. The boss (Stephen Root) has no time to give him any instruction except to keep away from Dean Zeigler (John C. Reilly), a client poacher, and to win that Two Diamond award at any cost.

Tim takes off for Cedar Rapids, Iowa, after carefully laminating all of his maps. It is only slightly less daunting and terrifying and utterly strange from him than a visit to Mars. He has never been on an airplane. And when a friendly young woman at the hotel doorway (Alia Shawkat of “Arrested Development”) asks him if he’d like to party, he assumes that it’s just the way they welcome people in the big city.

Surprise number one is that the black man in his hotel room is not a criminal, but his roommate, Ronald Wilkes (“The Wire’s” Isiah Whitlock Jr.), a very proper, buttoned-down insurance agent. Surprise number two is that there is a third roommate, none other than the decidedly unbuttoned Zeigler, a loud, hard-drinking, dirty joke-telling cynic and instigator of trouble. With Joan Ostrowski-Fox (Anne Heche), a very pretty agent from Nebraska who is intent on living it up while she’s away from home, Tim starts to learn some important lessons about his ability to say yes and his ability to say no. And his ability to figure out which is required in a wide variety of unprecedented, unexpected, and highly anxiety-producing circumstances.

As we saw with Helms in “The Hangover,” it is always a lot of fun to see a guy who is tightly wrapped let go — and then to get to see him deal with the consequences. The boss tells Tim that he once thought, “Here’s a kid who’s going to go places,” but then he never did. He goes places and then some in this story. Most of us spend a good bit of time coping with “impostor syndrome, worried that everyone will catch on to our inadequacy. There are a lot of moments of awkwardness and insecurity, but it is heartening to see Tim begin to learn that there is not as big a gulf between him and other people as he thought, even people of exalted rank, and to see him apply what he has learned to get a better understanding of what he thought he knew about the people back home. It benefits from a strong structure, astute depiction of the inevitable corny humor and cheesy networking activities of business gatherings, gutsy performances, and genuine affection for its characters. You will even have a whole new appreciation for insurance. Really. (more…)