"The Daily Show" alumni Ed Helms plays Tim Lippe, a small town insurance agent. He's a teetotaler manchild with a big heart.
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One day he's taken out of his comfort zone and sent to a big convention in Cedar Rapids, Iowa, with an important mission: he must win the coveted "Two Diamonds" award for his firm. The great Kurtwood Smith plays Orin Helgesson, the organizer and jury of the convention.
Tim soon meets fellow attendees Ronald Wilkes, Dean Ziegler (John C. Reilly) and Joan Ostrowski-Fox (Anne Heche).
A scavenger hunt is organized, with Tim and Joan forming a team. They like each other and sparks begin to fly, culminating in a night spent together.
The following morning, Tim is distressed when he finds out that in order to secure the award for his firm, he will have to bribe Orin. He reluctantly agrees to do this, though it leaves him ashamed of himself. In this depressed state, he befriends a prostitute named Bree (Alia Shawkat) and accompanies her to a wild party where he lets go of all his inhibitions. Predictably, he runs into trouble, but is bailed out by his new friends, Dean and Ronald.
Feeling guilt-ridden, he decides to expose the foul play going on during the award ceremony. This gets him fired immediately, however with his new friends and outlook on life, he is no longer afraid to take on the world.
Best part of story, including ending:
The supporting characters where well fleshed out, bypassing their stereotypes.
Best scene in story:
The scene where Tim goes to sing an a cappella song about his insurance firm is great. It shows a hidden talent as well as implausible commitment to his job which really fleshes out the character. The scene is played completely straight, which makes it work.
Opinion about the main character:
Naive men with childlike behaviour are a common comedic trope, but Tim is also a nice guy at heart and that helps us empathize.