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Tim Lippe (Helms) was the guy people always thought would go places but then he just ... didnt. Hes been living in über-sleepy Brown Valley, Wisconsin his whole life, still "pre-engaged" to his 7th grade teacher Macy Vanderhei (Weaver), while selling insurance to protect other peoples dreams. But now, Tims stalled life is about to get a kick-start because, for the first time in his 34 years, hes 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 unconventional. From the minute he checks into his hotel with his ancient American Tourister and cummerbund money belt, its clear Tim has no idea how the modern world really works. He is soon smitten with seductive Nebraskan insurance agent Joan Ostrowski-Fox (Heche) and awed by his experienced roommates, the straight-shooting Ronald Wilkes (Whitlock Jr.) and the suspicious Dean Zeigler (Reilly). Disheartened when he comes face-to-face with corporate corruption, Tim is ultimately lured beyond the lobby into an urban jungle hes only ever seen on DVD and when it seems his life - and chances to succeed - have gone completely topsy-turvy, he finds his own unjaded way to turn it all around.
Tim Lippe has led a sheltered life in Brown Valley, Wisconsin, and thus has a simplistic view of the world, he liking the comfort of knowing everyone he comes across in his small town daily life. In his naive view, he believes his once weekly sexual encounters with Macy Vanderhei, who was his seventh grade teacher now recently divorced, is true love on both their sides. He loves his job as an insurance salesman for Brown Star Insurance, owned for twenty-five years by Bill Krogstad. Tim truly tries to do whats best for his clients. Brown Star has done well as a company largely because it has won the American Society of Mutual Insurers (ASMI) Two-Diamond award three years in a row, it awarded only to one agency a year based on private presentations made by competing agencies to the ASMI president, Orin Helgesson, at ASMIs annual convention in Cedar Rapids, Iowa. On behalf of Brown Star, those winning presentations have been made by the agencys wunderkind, Roger Lemke, who Tim and everyone else in their office truly admires. Brown Stars winning streak is threatened when just before the upcoming ASMI convention, Roger dies under somewhat shady circumstances. His death not only means that he wont be making the presentation this year, but those shady circumstances, which if they came to ASMIs attention, would taint Brown Stars reputation as ASMI has a strong Christian morality at its core. Bill decides to send Tim to the convention as Brown Stars representative despite Tim feeling non-confident in heading to the big city to fill Rogers big shoes. At the convention, Tim is ill-prepared to deal with the people he meets, from the three conventioneers with who he ultimately hangs - Dean Ziegler, Joan Ostrowski-Fox, and Ronald Wilkes - to Bree, the young woman loitering in the convention hotel parking lot, she who he is naively unaware is a hooker. They are all outside his mentality of that comfortable Brown Valley life. As Tim spends time with this group, he will have to come to some decisions about his life, including how far he is willing to go to make it four in row for Brown Star and what his decision means in a holistic sense to him.
Ed Helms
Tim Lippe
John C. Reilly
Dean Ziegler
Anne Heche
Joan Ostrowski-Fox
Isiah Whitlock Jr.
Ronald Wilkes
Stephen Root
Bill Krogstad
Kurtwood Smith
Orin Helgesson
Alia Shawkat
Bree
Thomas Lennon
Roger Lemke
Rob Corddry
Gary
Mike O'Malley
Mike Pyle
Sigourney Weaver
Macy Vanderhei
Inga R. Wilson
Gwen Lemke
Mike Birbiglia
Trent
Seth Morris
Uncle Ken
Christopher Lemon
Rock Climbing Dude #1
Sudhi Rajagopal
Rock Climbing Dude #2
Chris DiAngelo
Kurt Gambsky
Lindsey Alexandra Hartley
Pam Gambsky
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