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.
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.
Trying to capitalize on the popularity of the movie "E.T.", the chipmunks dress Theordore up as an alien. But things don't go as planned. The boys are disappointed they don't have a mother to go to the mother/son picnic with them, so each of them choose a woman for Dave to marry.
Alvin decides to change the Chipmunks' clean-cut image to a punkier, more rebellious one in order to gain more publicity; the Chipmunks start a singing telegram service to help buy some golf clubs for Dave's birthday.
Alvin is not happy about having to play an angel in the school play. But when he hits his head, he truly believes he is an angel. / Dave hires a nanny, and the boys can't stand her.