The special first aired on December 17, 1999, alongside Futurama on Fox, ten years after the premiere date of Groening's television series The Simpsons.

While in town, she meets Martini, a con artist penguin recently fired from the city zoo, from whom she buys a counterfeit Rolex watch.

When she returns home she finds her owner, Tim, sad that there "won't be any Christmas" and disappointed that Olive does not behave like a normal dog.

On the way to the bus station, a disgruntled Postman learns of Olive's plan and vows to foil it, stating he wants Christmas ruined because he cannot handle the increased strain on the postal system during the holiday season (it is later revealed that his first time on the naughty list triggered a downward spiral making him more vengeful and even naughtier).

At a nearby bar, the local patrons are initially hostile before Olive convinces them to be humble and rekindle their Christmas spirit, which they do.

Round John Virgin, the bar owner, takes Olive and Martini personally to the North Pole complex.

Due to the reduced flight weight tolerance because of the missing reindeer, Martini must find his own way home, but Olive helps deliver the presents to the world.