Ed Helms plays Tim Lippe, an innocent and idealistic insurance agent who is thrust into a larger and more complicated world at the Cedar Rapids insurance conference.
John C. Reilly portrays Dean Ziegler, a boisterous and outspoken insurance salesman who befriends Tim and shows him the ropes at the conference.
Anne Heche takes on the role of Joan Ostrowski-Fox, a fellow insurance agent at the conference who forms a unique bond with Tim.
Isiah Whitlock Jr. plays Ronald Wilkes, a straight-laced and pragmatic insurance agent attending the conference.
Stephen Root portrays Bill Krogstad, Tim's boss at Brownstar Insurance who sends him to the conference in Cedar Rapids.
Kurtwood Smith plays Orin Helgesson, the self-righteous figurehead of the insurance convention known for his moral standing.
Alia Shawkat appears as Bree, an unconventional and free-spirited young woman who hangs around the conference and interacts with Tim.
Thomas Lennon plays Roger Lemke, a successful and seemingly model insurance agent who is celebrated at the conference.
Rob Corddry is Gary, a colleague of Tim's who has a cynical view on their line of work and its conventions.
Mike O'Malley portrays Mike Pyle, a minor character who contributes to the dynamics of the insurance agents' interactions at the conference.
Sigourney Weaver plays Macy Vanderhei, Tim Lippe's former teacher and current casual girlfriend, who is an influential figure in his life.
Seth Morris appears as Uncle Ken, a character presenting the quirks and idiosyncrasies of the small-town life that Tim Lippe hails from.
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