Hoping to win some money, the boys enter Theodore in a wrestling competition against Mr.Fabulous. / The Chipmunks visit their grandparents and help them save their farm.
The melodramatic episode which the Chipmunks' very first adopted kitten gets killed in a traffic accident, and Dave sympathizes with the Chipmunks noticing they are heavily depressed due to the loss.
After a concert, the Chippettes meet up with Olivia, an old friend from the orphanage in Australia where they grew up. They explain how they escaped from it and its evil headmistress and came to be singing sensations.
Bullies steal Dave's antique pocket watch, and the Chipmunks enlist the aid of Mr. T to retrieve it; the Chipmunks meet Brittany, Jeanette, and Eleanor for the first time.