Theo Knows Best is an episode of the ALVINNN!!! and The Chipmunks series.
While The Chipmunks and The Chipettes walk down the sidewalk, Theodore jumps happily into piles of leaves until he notices a piece of paper. He excitedly rushes to show the others only for Alvin to doubt its legitimacy. Simon confirms the paper appears real and Alvin attempts to weasel his way into sharing the prize. They each express what they believe is the best way to use the cash: Alvin wants a dangerous go-cart, Eleanor an oven master, Brittany a fashion gift certificate, and Simon computer upgrades. Jeanette finally cuts them off for being selfish and not considering what Theodore wants. As a result, the youngest chipmunk daydreams about a world of sweets. Waken from his dream, Theo spots a girl cold, siting on a bench across the street before running to catch up to the others who continued walking. At school, his brothers and fellow classmate try to convince him of their wishes or throw out a bunch of other ideas ranging from a robot to a rocket ship. Following hours of arguing, Theo sneaks away during which he drops his ticket and the girl he spotted earlier picks it up and returns it to him. He sees her enter a building Eleanor identifies as the homeless shelter before they head home. Dave finishes a phone call confirming Theodore get the money and Dave recommends he save it while Alvin makes a desperate effort to get him to spend it on the go-cart. Theodore, knowing what he wants to do with the winnings, gives it all to the homeless shelter, with Dave's help. Convinced Theo is lucky now, Alvin tries to convince him to look in trash bins and gutters for the next lottery ticket, earning him an "ALVINNN!!!" from Dave.
- "I Think You're Yummy" 
- "Run the Runway" is briefly heard in the background during Brittany's idea.
- When Theodore crashes the car in Alvin's dream, he makes the same groaning sound that he made in Something's Fishy when he was tackled by Alvin.
- Goof: In Eleanor's dream, she is baking chocolate chip cookies but the batter she demonstrates it with is pink.
- When this episode premiered in the US, it aired with a re-run of The Gift.