Lizzy Caplan, Catherine O'Hara, Alexandra Breckenridge, Kevin Kline
Shaun Brumder is an A student and class president at Vista Del Mar High School in Orange County, California. It has always been his desire to go to Stanford. He lives in a nice house with his mom Cindy who married a second time, and although Bob has money, he is now in a wheelchair and heavily medicated so he can hardly function. His loser brother Lance lives with them.At the start of the movie Shaun is narrating. He is actually reading the letter he is sending along with his book "Orange County" to Stanford professor Marcus Skinner, who wrote the book "Straight Jacket" which Shaun found on the beach and read many times. It changed his life and inspired him to become a writer. The audience sees flashbacks of events recalled by Shaun.Although he does very well in school, Shaun has one weakness. When his friends Lonny, Arlo and Chad want to go surfing, he goes with them. It doesn't matter how important other activities are. And on April 15 the group just has to take advantage of these killer waves. Lonny's funeral follows.One morning Lupe is fed up with being bossed around by Shaun's mom, who does little other than drink, and she decides to quit. Shaun persuades her to stay, speaking in Spanish so his mom won't understand. Bob needs his pills.After the audience sees Shaun find the book that changes his life, Shaun sends the letter.Lance, lying on the floor, gets bumped by Shaun opening a door. He asks Shaun to provide him with urine so he will pass a test required by his parole officer.At school, Shaun's girlfriend Ashley tells Principal Harbert that she wants to help save animals affected by an environmental disaster.Time has passed. It is the anniversary of Lonny's death and Shaun and his friends want to do something special. In English class, Mr. Burke announces they will be studying "Romeo and Juliet". Lonny's girlfriend and shallow cheerleader Tanya just can't. She's still grieving. Then class is interrupted by a female student telling Tanya she got into Stanford. Tanya's depression mysteriously disappears. Shaun drops everything and calls Lance on his cell phone. Shaun tells Lance to check the mail, and Shaun rushes home to find a thin envelope.Having been rejected by the one school he applied to, Shaun goes to guidance counselor Ms. Cobb and demands to know what happened. Ms. Cobb doesn't remember that she talked to Shaun earlier or even that Shaun is a student. In a previous scene she said he was definitely getting into Berkeley, and Shaun had to correct her. Ms. Cobb calls up the transcript on her computer and sees Shaun has a 2.5 GPA and a 970 SAT score. Shaun knows this is wrong and looks at the transcript. It is Shane Brainard's. Meanwhile, a clearly inadequate Shane announces to his friends he applied to Stanford as a joke and actually got in. Shaun blames Ms. Cobb for sending the wrong transcript and nearly attacks her.Shaun leaves the building walking right through a group of cheerleaders dancing to "Butterfly" by Crazy Town.What to do? Shaun's father Bud is very rich and he could donate money to Stanford and get Shaun in. He and Ashley drive to Bud's huge mansion on the Pacific Coast Highway where toddler Jake is misbehaving and his mom Krista, wearing a bikini, can't control him so she asks Rosa to. Krista invites Shaun in but his father is yelling at someone on the phone. When Shaun talks to Bud, Bud indicates he won't do anything to help because Shaun is throwing away his life. Bud says even though he fears his health isn't good and he may not have much time left, he will devote all his energy to keeping his business going so he can leave it to Shaun. Meanwhile, Krista is making out with Jorge, and Ashley, who waited in the car, rescues a dog which is about to get run over.Ashley admits she wants Shaun to go to Orange County University with her. She is going to study marine biology there and she is afraid they won't be able to stay together otherwise.There is another way. How could someone like Tanya get in to Stanford? Her grandfather Arthur Gantner is an official there. Ashley tells Tanya what she knows about her. The audience sees flashbacks of Tanya in bed with a guy at a Halloween party and several other incidents Tanya would rather not make public, including one after Lonny's funeral. Soon, Shaun has just minutes to prepare for a home visit from Mr. and Mrs. Gantner. Shaun has to get his mother to change into clothes that make her look presentable, and he tells Lance to stay hidden.The Gantners arrive and Shaun welcomes them, and tells them how much he wants to go to Stanford, and everything Mr. Gantner needs to know in order to accept him. Shaun's mom comes in drinking and volunteering way too much information, including that Bud left her for a 20-year-old and the details of how she ended up with Bob. Some of the details are not appropriate for polite company. Lance comes in wearing only underpants and socks and asks where his urine sample is. Then he realizes the small glass beside Mrs. Gantner must be it. Arlo and Chad come to the door wanting Shaun to come surf, and announces they heard he tried to kill Ms. Cobb. And Bob needs his drugs. Somehow Lance, whose drugs are kept in aspirin and Tylenol bottles, got his drugs and Bob's drugs mixed up and sold Bob's drugs. The rescue dog also causes trouble. The Gantners have had enough and leave, and as Shaun is trying to change their minds, Bob in his wheelchair rolls down the stairs and bumps the car. Mr. Gantner says Shaun will never get into Stanford.What to do now? Lance says Shaun should just go to Stanford and pretend to be a student. And then Lance decides to drive him there in a Ford Bronco. Ashley comes along. Lance is not that good a driver, constantly getting distracted and almost hitting several cars.Bud comes over to his ex's house and admits he misses her and has sometimes driven to her house hoping they will get back together. They end up in bed.By the time the young people arrive at Stanford, it is long past dark, but Mona the receptionist is still in the admissions building. Amazingly, Shaun thinks he can ask to see the dean of admissions. Mona explains that is late and won't even give them information allowing them to talk to the dean at home. After they leave, Lance sneaks in, while Shaun and Ashley figure out they can find the dean's address. Dean Durkett's teenage daughters argue while his wife is busy packing for vacation. Shaun finally persuades Dean Durkett to look at his transcript and while Dean Durkett is impressed, he says it is too late for Shaun to get in. While the dean is out of the room, Ashley discovers she has Lance's aspirin and Tylenol bottles. The dean comes back and sees them and asks for something for his pain. Ashley is unaware of what she is giving the dean, and soon he is high and can be persuaded to do anything.Meanwhile, Lance started taking his clothes off in front of Mona, and after Mona has also taken her clothes off, Mona shows Lance the list of students who were accepted. Lance sets it on fire and throws it in the trash. When the dean, who can barely remember who he is, arrives with Shaun and Ashley, the building is in flames and Lance and Mona are leaving. A firefighter interrogates Lance, who claims he knows nothing and was just walking around the neighborhood. The firefighter soon has enough information to get Lance in trouble and Lance, Shaun and Ashley leave before they get arrested.Shaun and Ashley go their separate ways and Shaun meets Gretchen, who is reading Faulkner, and they have a conversation. Gretchen eventually invites him to a party at Alpha Rho Chi house. She introduces him to some other girls and then the whole group starts dancing to "Butterfly" by Crazy Town.Shaun goes upstairs and can see Ashley talking to Kip, who is good looking and intelligent. He falls off the balcony and he and Ashley get in an argument.Shaun sees Professor Skinner and tells him who he is. Skinner remembers him and says he was impressed by Shaun's book about his life and as they talk, Skinner says he thinks Shaun will be a good writer.Eventually Shaun is able to persuade Ashley to leave with him. With Lance back in the Bronco, they head home.Bud makes a large donation to Stanford for a new admissions building, but Shaun realizes he can stay in Orange County and be a writer. Bud announces he and Cindy will get back together. Shaun narrates the ending, where he buries his copy of Skinner's book on the beach hoping it will help someone else.