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During the Chipmunks’ benefit concert in Paris, Dave Seville (Jason Lee) suffers a severe injury, when Alvin (Justin Long) jumps on top of a scaffolding and a falling billboard sends Dave flying across the stage into some electric devices. After the accident, he is rushed to the hospital. Although he survives, he must stay for a few days to recover, so he leaves his lazy 21-year-old cousin Toby (Zachary Levi) and Aunt Jackie (Kathryn Joosten) in charge of the Chipmunks until he returns. Prior to the event, Dave had made arrangements for Alvin, Simon (Matthew Gray Gubler), and Theodore (Jesse McCartney) to go to school. But, at the airport, Aunt Jackie falls down some stairs and an airport luggage trolley crashes into her. She has to go to the hospital too, so Toby is left in charge. Little does Dave know, on their first day at school, the Chipmunks feel uncomfortable with all the bullies around, when Ryan, one of the bullies, gives Simon a swirlie. The boys have fun being babysat by Toby, mainly because he is basically a big kid himself. Theodore tries to bond with Toby but Toby is always either ignoring him or being short towards him.

Meanwhile, Ian Hawke (David Cross) now lives in the basement of Jett Records. But, a FedEx mail comes to the building and a package falls out. And, three singing female chipmunks, The Chipettes, Brittany (Christina Applegate), Jeanette (Anna Faris), and Eleanor (Amy Poehler) come out of it and want to be famous like the Chipmunks. So they sing Put Your Records On to make Ian adopt them. He does, telling them that the Chipmunks ran away from him and left him broken-hearted, to make the Chipettes not trust them. He lets the Chipettes stay in his apartment and have their own dressing mirrors. Meanwhile, the Chipmunks enter the school concert to win $25,000 and save the school’s music program. The tension between Alvin and Simon continues to build as Alvin hangs out with the jocks of the school, but the one who is most affected is Theodore who believes he is losing his brothers with them fighting all the time. The Chipmunks meet the Chipettes and fall in love, until they discover they’re with Ian. The Chipettes sing Hot N Cold to get Dr Rubin, the school principal to enter them in the contest. The Chipmunks and the Chipettes compete against each other in a Battle of the Bands. Alvin warns Brittany about what Ian did to him and his brothers, but she doesn’t believe Alvin. Alvin then humiliates Simon in front of everyone when one of the jocks tricks him into thinking he’s now the school Litter Moniter and he ends up being thrown into the dumpster. At the concert, the Chipettes win after Simon and Theodore forfeit the competition because Alvin failed to show up (he hung out with the football team instead). Eager to get rich, Ian videotapes the Chipettes performance and posts it on YouTube, along with his phone number. Finally, Alvin shows up only to see that everyone’s gone. Brittany says to Alvin that he doesn’t care about anyone but himself and that she never wanted to win the way Ian was making her. When Alvin returns home, Simon and Theodore pretend they’re sleeping and ignore him. The embarassment is too much for Theodore to take who runs away to the zoo. When Toby and the boys find him and save him from an eagle, it brings out the best in all of them and the Chipmunks all forgive each other and go back to “One for all, and three for one”. (As Theodore put it)

Soon, the Chipettes are hired as the opening act at a Britney Spears concert at the Staples Center. Since the concert is on the same night as the school concert, Ian decides to blow off the battle and force the Chipettes to perform at the concert, threatening to barbecue them at a resturant if they don’t. At the school, Alvin gets a phone call from Brittany, saying that she and her sisters have been locked in a cage. Alvin races to save them on his red motorbike while Simon tells Jeanette how to open the cage on the phone. The Chipettes escape from the cage, climb out of the limo, and they jump onto Alvin’s motorbike. (The Chipmunks’ cousin, Digger makes a cameo during the chase) While being chased, Brittany apoligizes to Alvin for not listening to him about Ian. Ian pursues them with a R.C. helicopter, but they leap off the motorbike and grab onto the helicopter. Jeanette than snatches the remote and steers the helicopter away from Ian, while the motorbike drives straight into Ian’s groin. Simon and Theodore are about to forfeit the concert again, but Alvin and the Chipettes fly into the hall on the helicopter and they all sing We Are Family. Dave then comes back and watches them perform. Meanwhile, Ian dresses up as Brittany, performing in the center alone while people boo him, while the Chipmunks and Chipettes sing Shake Your Groove Thing. Finally, the Chipettes are re-adopted at the boy’s request and sleep at the Chipmunks’ house where Dave has another injury, tripping over Alvin’s skateboard and he yells the famous line “ALVINNNNNNNNNNNNN!” As the credits roll, the screen shows photos of the Chipmunks and Chipettes at the beach, at Christmas, in the kitchen, and in the garden. An epilogue shows Ian being thrown into a dumpster backstage by the guards.