Season 1

Alvin gives away his cherished harmonica to a sick little boy while, at the same time, Dave has booked Alvin to perform a harmonica solo at Carnegie Hall.

Dave has been suffering financial setbacks when all of his recent songs got rejected, which triggers feelings of depression and worthlessness. Dave starts believing that it would be easier if he never existed, and is then shown visions of all three of the Chipmunks' futures if that were indeed so.

Alvin, as usual, is thinking of himself when it comes to Christmas. He is so focused on receiving presents that he fails to think of poor Mr. Carroll, who just wants his morning paper. He is then taught a lesson in an homage to A Christmas Carol.

Alvin, Simon, and Theodore finish making invitations to send to their relatives and then leave to audition for the town play "Pilgrims Adventures in a New Land". Alvin trys for the role of the Lead, while Simon trys for Lighting and Sound director, and Theodore Costume Designer.