After Alvin, Simon and Theodore use Dave's antique gold pocket watch for Show & Tell at school, neighborhood bullies steal it. The Chipmunks find Mr.T to ask him for some advice and with his help they manage to get the watch back.

The Chipmunks make up a singing telegraph service to help buy some golf clubs for Dave's Birthday. But when Theodore loses the addresses, the boys are sent on a birthday mission, for a 100 dollar bonus. Except, that when Theodore wrote the number he wrote it upside down, so the Chipmunks end up going to the wrong house and are tricked into doing some different pranks for some highschoolers who are bored.

Dave hires a nanny to take care of the Chipmunks when he is away at work, and the Chipmunks will do anything to get rid of her.

Uncle Harry is up to no good again. This time, he makes Alvin a movie star so he can break up the Chipmunks.

The Chipmunks attempt to sell Theodore's famous muffins so they may buy Dave a new tape recorder for Father's Day, but Simon's hardening agent accidentally ending up in the batter causes the muffins to harden.

When Theodore loses a tooth, Alvin dresses as the tooth fairy.

Simon feels unappreciated and stows away on a cargo ship.