For the first time The Chipmunks meet their female counterparts, The Chipettes: Brittany, Jeanette and Eleanor.

A charaltan chipmunk named Harry claims to be Alvin, Simon and Theodore's long lost uncle and says he will have them see their mother as soon as they make enough money. The Chipmunks later not only find out that Harry is not their uncle but also the money he has them making is for a carnival strongman who he has owed for a long time.

The Chipmunks create a robot out of Alvin's video game, so that it can carry all of their equipment to their concerts. But, the robot goes beserk when it begins to capture every hat it sees, like the video game, it was created from, and It's up to Alvin, Simon, and Theodore to stop the robot.

Alvin tells a girl he wants to impress that they are famous and that they are going to be starring in a rock concert on live t.v., but Alvin must convince the producer to let him play.

Alvin unknowingly assists a jewel thief steal some jewelry from a cabin on their cruise ship, and Simon and Theodore begin to investigate the crime.

The origin of the Chipmunks is revealed, including how Dave ended up with the Chipmunks in the first place, as well as how their musical career got started.

Alvin and Simon have Theodore enter a wrestling exhibition under the name ""Mr.Fabulous"" and he goes up against a montrous Russian wrestler called Ivan The Terrible.

The Chipmunks meet their grandparents for the first time. Then, when they discover that someone is trying to take over their Grandparents farm, they decide to raise the money needed to save the farm.

Alvin convinces Theodore to dress up as an alien to attract more fans, but they also attract some investigators with the government who research ufo's. The investigators decide to kidnap Theodore and perform experiments on him and Alvin and Simon must think of a way to save him.