Tim Lippe (Helms) was the guy people always thought would go places but then he just ... didn't. He's been living in uber-sleepy Brown Valley, Wisconsin his whole life, still "pre-engaged" to his 7th grade teacher Millie Vanderhei (Weaver), while selling insurance to protect other people's dreams. But now, Tim's stalled life is about to get a kick-start because, for the first time in his 34 years, he's headed to a "major" metropolis - Cedar Rapids, Iowa - where he must try to save his company at a do-or-die insurance convention that, for him, will be entirely nonconventional. From the minute he checks into his hotel with his ancient American Tourister and cummerbund money-belt, it's clear Tim has no idea how the modern world really works. He is soon smitten with seductive Nebraskan insurance agent Joan (Heche) and awed by his experienced roommates, the straight-shooting Wilkes (Whitlock Jr.) and the suspicious Zeigler (Reilly).