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.

The Chipmunks start their own fire department.