Alvin wins the Publishing Warehouse Sweepstakes, a mail contest in which he has the choice of two prizes, $500 in cash or a mystery prize, which will range anywhere from a free lunch for four to millions of dollars. Alvin cannot make up his mind, so his asks Theodore for help. Theodore says to go with the mystery prize; when Alvin is concerned if that only turns out to be a free lunch for four, Theodore responds "What could be so bad about a free lunch?" Realizing Theodore is only interested in free food, Alvin then goes to Simon. Simon uses his time machine to look into two futures, the timelines dependent upon which prize Alvin chooses, but both showing the Chipmunks and the Chipettes married. The $500 future shows Alvin living in a mansion with Brittany, Simon and Jeanette winning Nobel Prizes, and Theodore and Eleanor co-owning a popular restaurant and nightclub. Alvin is encouraged by this, and wonders that if he invested $500 so well, imagine what he could do with millions! In the mystery prize future, Alvin receives a free lunch. Eating it made Alvin very ill, stopping his singing career, and bankrupts him, as well as the others. After watching this future, the time machine breaks. Jeanette consoles Simon on the destruction by saying the Nobel Prize ought to cheer him up, and Brittany demands Alvin get to the phone as he had to respond by 6 PM and it is close to expiring. Alvin calls to take the $500, with visions of big bucks, only to find out he is ineligible as he had to be 18 or older to win, dashing everyone's hopes of a great future.
2010 (Poor Timeline)
- Alvin Seville: Alvin is married to Brittany, has twin sons with her, lives in a tenement whose's front wall comes loose. He suffered acute food poisoning from the free lunch, and does not appear to be employed, sitting in a rocking chair by the fireplace and feeling regretful he has let everyone down.
- Brittany Seville: Brittany is married to Alvin, and is shown to be a housewife. She cooks Christmas dinner, which consists of one bean per person, and is bitter that Alvin did not take the $500 cash as she recommended.
- Alvin Seville, Jr.: He has to serve as a table leg, holding up the kitchen table with his head since they are too poor to afford a replacement leg. He and his brother reminisce about better days.
- Al Seville Jr: He is the other son of Alvin and Brittany. He is shown with his brother, reminiscing about better days.
- Simon Seville: Simon is self-employed. However, his accounting business is doing poorly as he works out of his car. He is balding, has a gray mustache and also seems weary like Alvin.
- Jeanette Seville: Jeanette is also presumably a housewife, or may aid Simon is his fly-by-night business. They appear to be childless.
- Theodore Seville: Theodore is a dirt farmer who brings a single turnip to Alvin as a Christmas gift. He also sold an old battered pickup truck.
- Eleanor Seville: The only female who is visibly employed, she helps Theodore on his dirt farm. She donates Theodore's entire profit of $2 from the sale of his pickup truck to Alvin and Brittany, as they are the poorest Sevilles.
2010 (Rich Timeline)
- Alvin Seville: Alvin is married to Brittany, has two twin sons with her, lives in a mansion and is a successful rock star.
- Brittany Miller/Seville: Brittany is also married to Alvin, has two sons with him and lives in the same mansion. It is unknown whether Brittany is still performing, or has given that up for the sake of being a full-time mother.
- Alvin Seville, Jr.: He is one of the two, twin sons of Alvin and Brittany. He is shown briefly with his brother, running and playing around the house. He and his brother both look identical to not only each other, but their father at age eight. Since he is named after Alvin, it could be possible that he is the most like Alvin.
- Al Seville Jr: He is the other son of Alvin and Brittany. He is shown briefly, playing with his brother, Alvin Junior.
- Simon Seville: Simon has a goatee and is married to Jeanette. It is stated that he has won the Nobel prize in physics.
- Jeanette Miller/Seville: Jeanette is married to Simon and dresses in a way that makes her look very similar to her then mother-in-law, Vinny. It is said that she has won the Nobel prize in literature, hinting that she may be an author now instead of a performer. Whether she has children with Simon or not remains unknown.
- Theodore Seville: Theodore is married to Eleanor and co-owns a popular restaurant with her.
- Eleanor Miller/Seville: Eleanor is married to Theodore and co-owns a popular restaurant with him. As with Simon and Jeanette, it is unknown whether she and Theodore have any children.
- "Everybody Have Fun Tonight" originally performed by Wang Chung.
- The year is 2010 in the future.
- Dave doesn't appear in this episode.
- "Publishing Warehouse" is a parody of the "Publisher's Clearing House Sweepstakes."
- It was revealed that if Alvin took the mystery prize, it would start a chain reaction as it was the free lunch, which gave Alvin acute food poisoning and ruined his music career, spiraling the Chipmunks into penury. This is an ironic answer to Theodore's innocent rhetorical question at the beginning of "what could be so bad about a free lunch?"
- A clip from the episode later appears in the episodes Alvin in Analysis and Chipmunkmania.