A Chip Off the Old Tooth is episode 29A in Season 3 (1985) of Alvin and the Chipmunks.
PlotWhen Theodore doesn't feel like eating, Dave, Alvin, and Simon become worried about him. Once they discover he's trying to pull his tooth out because he's afraid of seeing the dentist, they attempt to help him. Dave finds out and makes plans to take Theodore to the dentist. With some convincing Theodore decides to see the dentist and leave his tooth under his pillow afterwards. Alvin slipped the tooth into the laundry so Theodore doesn't get disappointed that there's no Tooth Fairy, but Simon tells Alvin to get the tooth back. They try to get Theodore to fall asleep, but Dave wakes him up to say good night. After Theodore sets up Dave's camera, Alvin dresses up as the Tooth Fairy and tries to "fly" in the window but it's closed. They were going to tell him the truth, but a quarter was mysteriously under Theodore's pillow with a picture of sparkling dust, possibly making the Tooth Fairy real.
- "Goodbye to You" (modified) originally performed by Scandal.
- The title is a spoof of the saying "A chip off the old block."
- This episode marks the fifth time Alvin's dressed as a girl.
- A clip from the episode later appears in the episode Alvin in Analysis.
- Part of the Alvin and the Chipmunks in Alvin's Wildest Schemes VHS.
- Part of The Alvinnn!!! Edition and Driving Dave Crazier DVDs.