On New Year's Eve 1999, Pizza Delivery boy Philip J. Fry accidentally falls into a cryogenic chamber and is frozen for 1,000 years. Finally unfrozen, he explores New New York, meets his new best friend (a kleptomaniacal robot named Bender) and goes to work for his great-great-great-great-grand-nephew's space delivery business.

During a Beastie Boys concert, Bender runs into a high school buddy, Fender. He invites him to a party, which turns out to be robots getting high off of electricity, or "jacking on". After one try, Bender is hooked.

Upon destroying the new DOOP headquarters, Zapp Brannigan and Kif find themselves court-martialed and dishonorably discharged. They take up jobs at Planet Express, where Kif learns what respect feels like and Zapp incites a mutiny against Leela.

Professor Farnsworth unveils his clone, Cubert Farnsworth, whom he plans to leave everything to upon his retirement. But Cubert wants no part of Farnsworth's lifestyle, prompting the professor into a premature retirement on the Near-Death Star.

The Professor's "What-If" machine simulates Bender, Leela and Fry's wishes. Bender discovers what it would be like if he were 500 feet tall, Leela discovers what it would be like if she were more impulsive, and Fry discovers what would happen if he never came to the future.

The combined explosions of a supernova and Fry putting metal in the microwave hurtle the Planet Express crew back in time to 1947. They land at Roswell, New Mexico, where a shattered Bender is mistaken for UFO debris, Zoidberg is taken in for an alien autopsy, and Fry accidentally kills his grandfather, Enis, in a nuclear explosion.

Desperate to learn how to play the holophonor in order to impress Leela, Fry swaps hands with the Robot Devil. He goes on to become a skilled holophonor player, winning Leela's heart and penning an opera about her life story, but the Robot Devil still has a trick or two up his sleeve.