Tim Lippe (Ed Helms) is an insurance salesman for Brown Star Insurance in Wisconsin. He is dedicated and loyal to his company and tries to do his best for his clients. It is time for the annual insurance convention in Cedar Rapids, and the company’s star salesman, Roger, is going once again to hopefully obtain the coveted “2-Diamond” award and rating from the company president. Tim has never been before.
An attractive, older woman rings the bell at Tim’s house. It is Macy (Sigourney Weaver), who, while being a client of Tim’s, is also having a fling with him. They have sex, and he tries to give her a “promise ring”, but she clearly isn’t interested. Later, Tim is woken up in the middle of the night with a phone call: Roger is dead. He accidentally killed himself while performing an auto-erotic act. Tim now has to go to Cedar Rapids for the ASMI convention, and must give a brilliant presentation in order to get the 2-Diamond award. He is thrilled and scaredTim has never been out of his small town, and never been on a plane or in a hotel. His boss, Mr. Krogstad (Stephen Root) warns him to steer clear of Dan Zieglar, a rep from another agency who also competing for the 2-Diamond.
Tim panics at the airport screening, as this is a new experience for him. He enjoys the bag of peanuts on the plane, and exclaims, “Sweet!” when he sees that he gets a red Aveo (small car) for his rental. At the hotel entrance, a cute young girl asks him if he wants any drugs or if he wants to party. He says no, but offers her butterscotch. Bree (Alia Shawkat) smiles, and says, “Goodbye Butterscotch” to Tim, and he likes the nickname. She picks up another john and leaves the hotel. Tim checks in the hotel, and is amazed that his room key looks like a credit card. He opens the door and is greeted by a huge “afro-american” man; it is his roommate, Ronald Wilkes (Isiah Whitlock Jr.). They have been upgraded to the Junior Suite as the hotel is overbooked, but they will get a 3rd guy in the room, to stay on the sofa bed. It turns out to be Dean Zieglar (John C. Reilly), the guy he was warned about. Dan is loud, crass, and veteran of the conventions, and knows everyone there.
Tim goes to workout in the hotel gym. A woman is also working out, and he eyes her. She introduces herself as Joan (Anne Heche), and is also an insurance rep, from Omaha. Tim meets the company president, Orin Helgesson (Kurtwood Smith), who reminds him that there is a lot of competition for the 2-Diamond award. He gives Tim extra drink coupons for the hotel bar to network and meet the others there.
At the bar, “Horizons”, he meets with his roommates and Joan joins them. Those three all know each other well from past conventions and drink shots and make jokes, and Tim, who doesn’t drink, is uncomfortable. He finally agrees to have a drink and orders a cream sherry, which makes the rest of the gang laugh. Back in the room, Dean tells Tim that there is a petition going around to revoke the 2-Diamond from his firm because Roger was such a deviate with a bad reputation for kinky behavior. Dean refused to sign it b/c he says that it is a business, and you shouldn’t have to be a boy scout to sell insurance.
At the ASMI convention opener, another insurance guy, Mike Pyle (Mike O’Malley) gives the invocation. He is a big competitor of Brown Star Insurance. Tim’s cell phone rings: it is his boss. He has already heard that Tim is hanging out with Zieglar, and is mad that Tim disobeyed his direction to stay away from him. After the speeches, Tim and Joan take a walk to the park nearby and sit on the swings and talk. She asks him why he is in insurance, and he tells her that after his dad died in a sawmill accident when he was young, the insurance agent fought for him and his mom, and he looks at insurance agents as heroes. “Wow, you make it sound cool, not “dweeby” marvels Joan.
The convention has a scavenger hunt, and the winning team gets to share a $45 gift certificate to a restaurant in the local mall. Tim and Joan are paired up for it, and win. They go out to dinner together, and being confident from the victory, Tim orders a cream sherry. They meet the gang back at Horizons and they get Tim to do shots. This is his first time ever drinking, and he gets drunk like the rest of them. Unbeknownst to Tim, Joan has signed him up for karaoke. He is mortified, but takes a shot and goes up. He introduces his song as one he sang at the company Christmas party, and begins singing “O Holy Night”…but the lyrics are changed to be about insurance. The crowd goes wild with applause, and Tim is having a good time. The gang leaves and sees a wedding going on, and Dean yells, “Free booze!” and they crash it, dancing and drinking with the wedding party. They leave, and Zieglar wants to take a swim, but the indoor pool is closed. He opens it up anyway, and waltzes in, in all his clothes. He puts the trashcan lid on his head, and they think he looks like R2D2. Ronald wants no part of the shenanigans and leaves for the room. Joan strips down to her underwear and gets in, and beckons Tim to join. He strips down to his tighty-whities, and gets in. Drunk Dean watches as Joan takes off her bra and gets close to Tim. They kiss, and then the boss, Orin, comes out of his room in his bathroom to tell the noisy people to be quiet, and sees who it is. He gives them a glare, and they grab their clothes and run to their rooms. Tim goes with Joan, and they make out, and then he exclaims, “I want to make love!” and they do. He stays the night with Joan and in the morning tells her it was “super-awesome”.
Ronald is primping in front of the mirror when Tim returns to their room and reminds him that he has his presentation with Orin in 10 minutes. Dean is passed out on one of the poolside tables, in his boxers.
Tim has remorse for his acts. He talks to Joan and thinks they should tell their significant others that they slept together. She says nowhat happens in Cedar Rapids stays there. He calls Macy anyways, and Macy is glad he slept with someone. She tells him she is like a momma bird, nudging the baby bird out of the nest to fly---he needs to move on and meet other women. She isn’t interested in being his girlfriend. He is devastated.
He talks to Joan, and thinks his life is over: he is now a philanderer, and has also botched their chances for the 2-Diamond award. She swore she wouldn’t tell, but she tells Tim anyway: Roger got the 4 past awards by bribing Orinhe paid him off. Tim tells Dean and doesn’t know what to do. Dean tells Tim that even though he is a blowhard he is there for the people who need him. He is 100% behind Tim and is his friend. He tells Tim to buy Orin off, to “show him the tiger’s teat” and let him see the cash.
Tim starts his presentation, but is interrupted by Orin, who tells him that his antics in the hotel pool have cost him the award, Tim begs for a second chance, and says he is “prepared to show him the tiger’s teat”, to which Orin is confused, shocked and alarmed. When he sees it is just cash that Tim pulls out, he smiles, and asks him how much he has. Tim has $1500, which he brought in case of emergency. Orin replies that this IS an emergency. He congratulated Tim, and tears up the petition.
Tim goes outside to think and sits in the park. Walking back to the hotel, he sees Bree. She says, “Hey, Butterscotch” with a smile and invites him to join her at her Uncle Ken’s for a party. He rides with them, and in the car smokes crack with her. He is wasted and in the party, which is out in the country. The gang is back at Horizons for the company talent show, and all wonder where Tim is. They call his cell phone, and he says, “I’m on drugs!” and tells them to come to the party. Dean gets directions, and they go to rescue Tim in Ronald’s minivan.
A tough guy starts a fight with Tim, and he is about to get beaten to a pulp, when in comes Ronald, in his black trench coat and tie. They start to laugh at him, and he puts his hand in his coat pocket, and talks tough, swears and tells them he always keeps “one in the chamber” for punks like this, and pats his chest. They think he is a ghetto-tough guy with a gun, so they let him take Tim. They get in the van and escape before they are all beat up. They ask quiet, subdued Ronald how he acted so tough in there, and he tells him he was copying his favorite character from the HBO show, “The Wire”. They all laugh together.
Back at the hotel, Tim tells the guys that he sold his soul, and can’t live with it. He is crashing from the drugs, and Joan offers to stay with him until he is ok. In the morning, Mr. Krogstad walks in; he had a call from Orin that Tim was amazing and got them the 2-Diamond award. He wanted to congratulate them, and tell him the news: he has a deal with Pyle that says if they did get the 2-Diamond award, Pyle would buy Brown Star Insurance. But, then Pyle is going to close it. Pyle is going to keep Tim on, though, at his Milwaukee office. Tim is shockedall the workers back home will be let go. He and his friends don’t like this, but come up with an idea: they all call Tim’s clients and talk to them.
At the convention closing ceremony, Orin announces that Brown Star Insurance won the 2-Diamond again. As Krogstad accepts the award, Tim interrupts and tells the crowd about the $1500 he paid to Orin, and apologizes to everyone there. Pyle won’t buy the company without the 2-Diamond award, so the sale is off. Orin is furious and yells at Tim, and says he fucked up a great deal, Tim tells him, “No, you fucked it up”. He tells him he quits, and is taking his clients with him. Orin doesn’t believe him, but Dean pulls out a stack of faxes from his clients, all vowing to go with Tim, wherever he works.
As the convention ends, they say good-bye to each other, and vow to stay in contact. They plan to get together at cousin’s cabin in Canada in the summer.
Tim flies home, and the flight attendant asks him about the cut on his head (from the fight at Bree’s crack party), and he tells her he got blotto on drugs, drank alcohol…and she tells him that he deserves 2 bags of peanuts. He smiles, proud.
(During credits, we see the three drinking at a cabin, telling jokes, and Dean shows them that he can light a fart on fire.. and does. Then we see a commercial for “Top Notch Mutual Insurance” with Tim, Dean and Ronald as owners, all very happy.)
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