Alvin goes through an identity crisis and starts trying all kinds of different personalities, with embarrassing results.

Alvin nearly runs over an elderly woman in the mall with his skateboard. When Alvin finds out that she is wealthy, he sends out invitations for a senior citizens' party in order to find her.

The Chipmunks and Chipettes get to perform on a high class cruise ship, the Island Lady, but instead they end up ship wrecked on an island.