This episode was broken up into two parts.
After The Chipettes finish singing "New Attitude" at a concert, The Chipmunks remind them of a big party at their house before leaving. The producer tells them that someone is here to see them and shows them a gold bracelet. The girls run out the door and see Olivia. Everyone is overjoyed but Olivia asks why the girls ran away, Brittany informs her that they didn't.
Several years ago, Miss Grudge, the owner of the orphanage, was forcing children to sing. Olivia found Eleanor in a cup of water, Jeanette playing with her spider friend Herman, and Brittany in Eva's jewelry box singing (which they are not allowed to do, or Miss Grudge would keep them at the orphanage forever). That night, Miss Grudge makes Olivia scrub the bathroom with the Chipettes' help hoping that they one day can go to America, which Olivia says is a land of opportunity and liberty. After hours of cleaning, Olivia didn't get any sleep and is forced to give up her charm bracelet so Eva wouldn't tell that the Chipettes sing. After finding out, the girls try to get Olivia's bracelet back, which ends up getting Olivia in trouble and they have to reveal who they are. Olivia gets adopted and is unable to find the girls as she's leaving because they were tied up and locked away by Eva and Miss Grudge.
Jeanette was crying that Olivia was gone, so Brittany tried to cheer her up by singing "Tomorrow" and the girls decide to break out and start a new life. The girls get packed and sneak past Miss Grudge and Eva to start a new life in America with help from Wendy the Kangaroo. They arrive at New York after stowing away on a cargo ship. The girls' actual view of America is not exactly what Olivia described, in which the streets are paved with asphalt, not gold, and problems are aplenty. The girls decide to audition, but that gets them nowhere. After many failures, they become waitresses while singing "Neutron Dance." After years of working, the girls still were poor and living in the park.
They decide to audition for a singing group in California. After some hard traveling on a bus, the girls make it to California, but they are too late. They try to get the auditioner to listen to them anyway but must follow him. When they catch up to him, they sing "New Attitude". This impresses the auditioner, who convinces his boss to give the Chipettes a recording contract, and thus their first big break.
Back in the present, the Chipettes go to the Chipmunks' party with Olivia. Olivia says that she is Alvin's biggest fan and wants him to tell her all about himself, which he does.
- "New Attitude" originally performed by Patti LaBelle.
- "Tomorrow" originally performed in the musical and film Annie.
- "The Neutron Dance" originally performed by the Pointer Sisters.
- "You Are Beautiful" replaces "New Attitude" on DVD.
- "Keep Dancing" replaces "The Neutron Dance" on DVD.
- This is the Chipettes' counterpart to The Chipmunks Story, as both function as a backstory episode showing the characters as babies and how they came to be where they are at the series premiere.
- Part of The Chipettes: The Glass Slipper Collection DVD.