Alvin's Oldest Fan is an episode of the Alvin and the Chipmunks series.
Alvin advertizes a publicity contest where people will send him postcards, and the whomever has the earliest postmark will get a night on the town with him in New York City. Simon determines the winner is Honey Ginger, causing Alvin to think a woman with a name like that must be some beautiful starlet. In New York, he finds out Honey Ginger is an elderly woman who is a Chipmunks fan. Alvin does not want to be seen with her, and pays a taxi driver to take her as far away as possible. When Simon and Theodore find out, they demand that Alvin help find her and honor his part of the contest. Simon determines by the direction the taxi traveled and the amount of money Alvin paid that Honey would have been taken as far as the pier. When The Chipmunks arrive at the pier, they hear the cab driver saying "the old girl has had it" and Alvin thinks Honey has been sent to the funeral parlor. Overcome with guilt, Alvin uses the remnant of his conscience to sacrifice his career so that Honey did not die. Simon then tells Alvin to pay up as Honey is seen on TV; the taxi driver's remark of "the old girl has had it" means he just bought a new taxi and sent his old one to the junkyard. When a tabloid reporters asks if Alvin ditched Honey, she denies it, saying that Alvin had some urgent matters and paid to send her on a tour of New York City, thus staving off bad publicity for Alvin. Alvin reunites with Honey Ginger, who admits she realized that not many senior citizens are Chipmunk fans and it would have been a surprise to Alvin to have her winning the contest. Alvin apologizes and makes good on the contest by having dinner with her.
- "Bad to the Bone" originally performed by George Thorogood & The Destroyers.