The film begins with Alvin (Justin Long), Simon (Matthew Gray Gubler), and Theodore (Jesse McCartney), along with The Chipettes – Brittany (Christina Applegate), Jeanette (Anna Faris) and Eleanor (Kaley Cuoco) – setting up a surprise birthday bash for Dave (Jason Lee) that also serves as a going away party for The Chipettes, who are moving out on their own to be guest judges on American Idol. Alvin invites and hires many people and celebrities to the dismay of Simon, before Dave returns home in dissatisfaction. Nevertheless, Dave agrees to take them to mini-golf, and meet the woman he has been dating for the past few months. While the Chipmunks like Samantha (Kimberly Williams-Paisley), her son Miles (Josh Green) is a bully who physically abuses the trio. Later, the Chipmunks find an engagement ring in a bag Dave brought home and believe that he’s going to propose to Samantha. They try to steal the ring but are unsuccessful. Dave has to produce a record for rising pop artist Ashley Grey (Bella Thorne) in Miami and decides to bring Samantha along with him. The Chipmunks and Miles are staying together, but they agree to head to Miami to sabotage the proposal. The Chipmunks drug three squirrels and dress them up in their clothes to fool their hard of seeing neighbor Ms. Price (Jennifer Coolidge), who was tasked with looking after them. The Chipmunks travel on a plane, but Theodore lets out several animals which cause an emergency landing and brings the ire of Air Marshall James Suggs (Tony Hale), who has a personal vendetta against the Chipmunks (Suggs’ girlfriend left him while “The Chipmunk Song (Christmas Don’t Be Late)” played in the background). The Chipmunks head to a bar and perform, but this is interrupted by Suggs and they cause a bar brawl as a diversion. They jump into a cab sitting outside. After the cab driver (Mark Jeffrey Miller) learns they can’t pay him, he kicks the four out of the cab. The Chipmunks and Miles rest, and he reveals that his dad left him when he was five years old. They raise money to take a bus to New Orleans, and sing “Uptown Funk”, which gets the attention of Dave when it is broadcast on live television, and allows for the Chipmunks to cause Suggs, who has followed them to New Orleans, to get drunk. Dave and Samantha meet up with Miles and the Chipmunks and proceed to take them to Miami. Because the Chipmunks are now on the No-Fly List, Dave has to drive the boys over. When they get there, Alvin reveals that he stole the ring from the container, thus ruining the proposal. However, Miles had bonded with the Chipmunks and was upset that they were celebrating over this. He crosses the street with his headphones on and is almost hit by a car, but the Chipmunks swing Theodore and push Miles out of the way, saving his life. They agree to give the ring back. During the dinner, Suggs catches up with the Chipmunks, but they trap him in an elevator. Miles and the Chipmunks return the ring to Dave, who reveals he never intended to propose to Samantha, and the ring belonged to his friend Barry (Eddie Steeples). Dave is very disappointed in the kids, so they try to make it up to him by singing a new song to him at the launch party with the help of The Chipettes, Ashley, and Miles. Having forgiven them, Dave returns home with the Chipmunks and takes them to a courthouse where he officially adopts them. Dave claims that nothing could ruin his day, but returns home to see the squirrels had destroyed everything. He then predictably screams Alvin’s name. In a mid-credits scene, Suggs has escaped the elevator and decides to relax by the pool, only for two security guards to carry him away. Cast[edit]