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A childlike insurance salesman discovers his inner grown-up in this comedy from director Miguel Arteta and producer Alexander Payne. Tim Lippe (Ed Helms) sells insurance for a living. He's passionate about his career, so when the top salesman at the company dies on the eve of a big industry convention in Cedar Rapids, IA, his boss, Bill (Stephen Root), decides that Tim should take the trip to represent their company, and possibly accept a major award. Trouble is, not only has Tim never been on an airplane before, but he's in such a state of arrested development that he's even started sleeping with his former elementary school teacher Mrs. Vanderhei (Sigourney Weaver). Arriving at the convention ready to put his best foot forward, Tim hits it off with his hotel roommate Ron (Isiah Whitlock Jr.), but is soon thrust out of his comfort zone when he learns they will be sharing a room with their amoral, hard-partying colleague Dean (John C. Reilly), whom Tim has been instructed to avoid at all costs. Later, when the three unlikely roommates meet up with fellow insurance slinger Joan (Anne Heche), the chemistry just clicks. However, when the ultra-conservative president of the entire organization (Kurtwood Smith) catches Tim in a compromising position, it all starts to fall apart. Now, if Tim can just shed his illusions and finally see the truth about the people he always looked up to, perhaps he can find the courage to recapture his integrity, and return home and face the future with a newfound sense of self-assurance.