It's December 31st, 1999 in New York City; and Fry is having a cruddy night at his pizza delivery job, like usual. His boss tells him he has a delivery, and Fry is off. One bad thing leads to another. First he sees his girlfriend, Michelle, riding in a cab with another man. When Fry asks where she is going, she just tells him it's not working out; and the cab speeds off. Fry continues on angrily and reaches his destination, a cryo chamber building. Soon after locking up his bike outside, it is stolen. He goes upstairs only to find out that the name of the person the pizza goes to, I. C. Weiner, is a fake. So, Fry sits down and decides to eat the pizza by himself. Soon, the countdown to midnight has begun. As soon as it hits zero, though, Fry falls back out of his chair and into a freezing chamber which was set to open in 1,000 years...
The chamber opens up on December 31st, 2999. Fry gets out a little bewildered about what had happened. When he takes a look out the window and sees what New York have evolved into, he realizes what had happened and with joy greets the future. After two men introduce Fry to the "world of tomorrow" they take him to a Fate Assignment Officer in order for him to get a permanent career assignment. This is when Fry first meets Leela, a one-eyed alien. After a small series of tests, Fry finds out that he has one living relative, Professor Hubert Farnsworth, his Great, Great, Great, Great (times 30) nephew. Things seem to be looking up for Fry, that is until he finds out what his permanent career is. He finds out that he is destined to be a delivery boy. Leela insists that he has to do what he has to do and tries to install his career chip into his palm, but Fry runs away. He tricks Leela and she accidentally falls into a freezing chamber. Fry is about to leave her; but, feeling guilty, he decides to set it for five minutes, just long enough for him to escape into the city.
Fry is now out on the streets of New New York experiencing the world of 2999. He decides to call Professor Farnsworth, so he gets in line for a phone booth. Little did he know that it wasn't a phone booth, but it was actually a suicide booth. Behind him in the line is Bender, a cocky, wise-cracking robot. Bender and Fry have a small quarrel, but Fry ignores him and get into the booth. He doesn't know how to work it, so Bender comes in and says that he can get them a double kill for the price of one. Fry finds out that it is a suicide booth and manages to save himself and Bender from the knives and zappers that came out of it. With nothing else to do, Bender suggests that the two go and get drunk.
Leela gets out of her chamber and continues her pursuit of Fry. Fry and Bender are at a nearby bar enjoying a drink. Fry tells him of his troubles and Bender tells Fry of his. He is a bender that was designed only to bend girders. After finding out that the girders were used for suicide booths, he couldn't go on living. While they are drinking, Fry notices Leela outside showing his picture to people seeing if they've seen him. Leela spots them and Fry and Bender are on the run again. They run and hide in the head museum. There they meet the head of Leonard Nimoy and chat with him for a minute or two until Leela and two cops come in and storm the building. They see Bender and Fry and the cops use force to bring them down after Fry accidentally knocks over the jar containing President Nixon's head in it. When Leela tries to intervene saying that they don't need to use force they tell her to keep her big nose out of it and Leela kicks them around in anger, allowing for time for Bender and Fry to get away.
Bender and Fry make their way to the sewers which contain the decaying remains of Old New York. Fry looks upon what the city once was, the city that he had once known, and realizes that everyone he ever knew or cared about was gone. Just after, Leela catches up. Fry says that she couldn't possibly understand his loneliness, but she says that she does. Leela reveals that she is an alien from another planet that had been abandoned as a baby and she doesn't even know where she came from. Fry realizes that he can relate with her so he gives up and tells her to insert his career chip. Leela has a change of heart, however, and instead takes out her own chip. Now with no jobs and nowhere else to go, they head to Professor Farnsworth's. After a little convincing and a DNA test, the Professor realizes that he is Fry's nephew. He shows them around and tells them of his delivery business; but the tour is cut short when the police catch up to Fry, Bender and Leela and order them to come out. They quickly head for Farnsworth's intergalactic spaceship and take off. Thanks to the New Years' Celebration going on outside, the ship was well hidden within an explosion of fireworks in the sky.
Fry comes to realize that without jobs that they would be fugitives forever. Then the Professor suggests that they could become his new spaceship crew. Leela says that they would, but they don't have the proper career chips. Luckily, the Professor had saved the chips from his previous crew (who obviously had a gruesome death). Fry then realizes that he will be a delivery boy, but doesn't seem to care.