Air date: 11/2/99
Dilbert's mother's birthday is coming up, and in an attempts to find his mother the perfect birthday present, Dilbert returns to the mall, where he was abandoned by his father when he was a child, to confront his fears and find the perfect gift. He discovers his long-lost father has been holed up at the food court for the past ten years, obsessed with the challenge of an "All you can eat buffet", he tells Dilbert to give his mother a video of him, and give her a message. In the end Dilbert ends up getting his mother a gift certificate, which she hates, but she is touched when she learns that he confronted his fears simply for her. Together they watch the video of his father, and he gives her the message.
The Shroud of Wally
Air date: 11/9/99
Dilbert has a near-death experience when he has an accident at a gas station. Meanwhile, a group listening to a multi-level marketing speech become hypnotized, and through a bizarre accident create a religion based on Wally.
Art
Air date: 11/16/99
Dilbert is assigned to create a digital work of art. The result ends up appealing the lowest common denominator of society and as a result destroys the value and popularity of classic artworks.
The Trial
Air date: 11/23/99
Dilbert is sent to prison after being framed by the Pointy Haired Boss for a fatal traffic accident; once inside, he applies his knowledge of mathematics and engineering to prison life and takes over his cell block.
The Dupey
Air date: 11/7/99
Dilbert's attempts to design a children's toy go horribly awry when they gain sentience and mutate into hideous yet benevolent creatures that want independence.
The Security Guard
Air date: 1/18/00
After a heated debate, Dilbert and the building's security guard trade jobs, with whoever being the better at the other's job winning. However Dilbert quickly finds himself hopelessly out of his league when he discovers an illegal casino being run underneath the building.
The Merger
Air date: 1/25/00
The Boss decides that the company needs to merge with another, and chooses a company of brain-sucking extraterrestrials.
Hunger
Air date: 2/1/00
Dilbert almost ends world hunger by creating a new, safe artificial food, but it turns out to taste so horrible that not even people dying of starvation will eat it.