Driven to the brink of insanity by his appointed status as designated driver, Barney Gumble drives to downtown Manhattan in Homer's car, leaving it there. But when the family journeys to the Big Apple to retrieve their property, Homer faces a one-on-one showdown with the dreaded boot.
When Moe's "evening rush" comes into the bar one night, he tells his customers that they are responsible for 91% of all traffic accidents in Springfield. This prompts Moe to hold a pickled egg drawing to see who will stay sober and be the designated driver ("whoever draws the black egg, stays sober tonight." He also remarks that this is how they picked the Pope). However, Barney, the most unlikely one, draws the black egg and therefore becomes the designated driver. However, while his friends enjoy drunken antics, the Duff van arrives at Moe's with a bottomless mug of icy cold beer for Barney. Barney has an outburst, saying that he is the designated driver, and Duff Man remains at the bar to party with the drunks. Then Barney drops off Lenny, Carl and Homer at their homes, each of them suggesting a nonsensical destination (which Barney refers to as "sweet, beautiful drunk talk"). Barney promises an inebriated Homer that he will bring his car back the next day, but this proves not to be true and disappears.
Two months after Barney drops Homer at home, the car has still not been brought back. Homer has been putting up signs, which Moe says is a lost cause. Then Barney arrives in the trunk of a limousine, completely hungover with no recollection of the last two months (except for "giving a guest lecture at Villanova ... or maybe it was a street corner!"). Homer then rides angrily off on a scooter to pick Bart and Lisa up from school. Homer proceeds to construct a new car out of a mattress and other various parts from the garage (with Marge knitting him seat belts). However, Lisa bursts in with a letter from New York City, saying that Homer's car is parked in the borough of Manhattan and that he needs to pick up his car in 72 hours or it will be thrown into the East River. It is then Homer reveals to the family that he had been to New York before when he was 17-years-old and had a very bad experience where, when attempting to find a coat outlet for an irregular coat, he had to stop at New York City and paid a photographer some money for a picture, only to discover that he was jiffed out of his money, and later had his briefcase stolen by a Police Officer who he tried to report what happened, and ended up having his wallet and hot-dog stolen by a street thug and a pigeon, respectively while he was watching an electronic billboard and had trash dumped on him from an apartment denizen, and was forced to run for his life when he accidentally threw a banana peel at a pimp and tried to escape via a fire exit ladder, but ended up falling into a manhole cover due to the ladder coming loose and attacked by CHUDs. But because travel fare is so cheap, he reluctantly agrees to go back on the grounds that he can get his car and leave, as well as burning his wallet to ensure that New York doesn't steal it.
When Homer arrives in New York, Marge, Bart, Lisa and Maggie go off to explore the city while Homer goes to the World Trade Center, finding his car full of tickets and a boot on the wheel. Homer tries to pry the boot off with his hands, but a loud bystander tells him he needs to call the phone number on the boot. After the phone call, Homer learns that he needs to wait by his car for a parking officer between the hours of 9 A.M. and 5 P.M. He hungrily devours Khlav Kalash out of a passing cart and drinks can after can of crab juice. However, he then has to go the restroom, and the man driving the cart tells him to go to the observation deck at the top of the South Tower. Homer doesn't want to leave his car, but it soon becomes too much to bear. He rudely cuts in front of everybody in the line but upon reaching the top floor, the bathroom is locked and out of order. Homer then races out of the South Tower and goes to the top of the North Tower, where he relieves himself. However, once he finishes, he sees the parking officer, who hadn't shown up for the whole day, giving him a $250 ticket for "failure to wait by vehicle." Infuriated and desperate to rescue his car from the East River, Homer drives out of the World Trade Center with the boot still on his tire. When he realizes that he won't be able to get very far, he distracts a construction worker and uses his jackhammer to pry the boot off his tire. However, it then gets stuck on his foot, so he kicks the front of his car until it comes off. At this point, Homer has completely wrecked his car and is speeding off to get his family.
Meanwhile, the rest of the family have had a wonderful time. They watched a Broadway musical and visited several ethnic neighborhoods, concluding with a carriage ride in Central Park. Homer speeds through bridges and ponds to get to his family, who jump into his car and leave as fast as possible, only to stop one second later to throw the Carriage driver out of the car, who yells back: "Tell your friends to ask for Jimmy!" While driving back to Springfield, the family reflect on their wonderful time in the city while Homer's hatred for New York remains. When Lisa says "Can we come back next year, Dad?", Homer's eye is twitching and he says "We'll see, honey. We'll see." as garbage flies from a truck on Homer's face. The credits use the song "New York, New York".
This episode was aired four years before the 9/11 terrorist attacks. Due to the central plot being a dilemma that Homer has at the World Trade Center, the episode didn't air in the United States for a long time (many viewers thought it would never come back). After an appropriate amount of time passed, some stations began to air the episode again. The episode remained in somewhat constant syndication in Australia, with regular reruns playing on the Cable Channel FOX8. It is shown uncut on the Season 9 DVD. The episode was also kept in regular syndication in Canada, airing on Global, Omni 2 and CBC.
On the DVD commentary for the episode, Executive Producer Josh Weinstein remarks that the line "They stick all the jerks in Tower One," spoken by an occupant of Tower Two after the Tower One occupant shouts obscenely at Homer, is "regrettable."
In the United Kingdom, the British satellite TV channel Sky One did not show the episode again until August 7, 2005, with several cuts to remove some (but not all) shots of the towers. The episode was pulled from the first showing of season 9 on terrestrial TV (then running on BBC2) as it was due to be shown shortly after the attacks. The show finally aired on British Terrestrial television on Channel 4 on October 7, 2007, although the "jerks in tower one" line was removed.