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 so they'll now have to have designated drivers to prevent anymore accidents. This prompts Moe to hold a pickled egg drawing to see who will stay sober and be the designated driver. Barney, the most unlikely one, draws the black egg and therefore becomes the designated driver. 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 (Lenny suggesting the "Girls college", Carl the "playboy mansion" and Homer the "Lost City of Gold" all of 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 as he undergoes a severe mental breakdown and disappears.
Two months after Barney drops Homer at home, the car has still not been brought back and Barney has completely vanished. Homer is hanging signs claiming the car as missing and that it was last seen with Barney, but Moe tells Homer to just give up and accept that the car is gone and Barney is never going to come back. Ironically, Barney then arrives in the trunk of a limousine, completely hungover with bloodshot eyes, discolored skin and most of his motor skills absent. Homer furiously demands to know what Barney did with his car, but Barney tells him he has no recollection of any events that happened over 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 three days or it will be (at his expense) thrown into the East River. Homer is frustrated and refuses to go claiming New York as a "hell-hole". Lisa tells Homer that he can't just judge a place he's never been to before. It is then Homer reveals to the family that he had been to New York before when he was 17, and had a very bad experience where; he was on his way to a coat outlet in Harrisburg Pennsylvania for an irregular coat but he had to stop at New York City and walk from the port authority bus terminal to Penn station to catch his train. On his way he paid a photographer some money to take his picture, only for the man to run off with his camera and money. Later he was giving a police officer a report about what happened only for the office to grab his briefcase and run. Even later while standing at a cross walk and looking at an electronic billboard (stating crime was up 8 million percent) when a thug pickpockets his wallet, a seagull steals his hot dog and trash is dumped on him from an apartment denizen. Though it seemed things could not have gotten worse, they did when he accidentally threw a banana peel at a pimp resulting in him being chased through the streets and down an alleyway. Homer then tried to escape via a fire exit ladder, only for the ladder to come loose resulting in him falling down into an open manhole and getting attacked by CHUDs. Marge tries to change Homer's oppinion by telling him that he'll always have a bad opinion if he only focuses on the negatives. This doesn't change Homer's views, but because travel fare is so cheap and the rest of the family want to go, 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 it's not stolen again.
When the family arrive in New York, Marge, Bart, Lisa and Maggie go off to explore the city while Homer goes to the World Trade Center to retrieve his car. He arrives finding his car parked in the middle of the plaza, 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 that the only restrooms are at the observation decks of the towers. Seeing how this means he would have to leave his car, Homer tries to resist, but it soon becomes too much to bare. He rudely and desperately cuts in front of everybody in the line but upon reaching the top floor to relieve himself and make it back to his car in time. Unfortunately, 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 looks out the window and sees the parking officer, who hadn't shown up for the whole day, giving him a ticket. Homer's subsequent "D'oh!" echoes across the entire city, reaching his family on the observation deck of the Empire State Building. Homer rushes out of the tower and reads the ticket stating that for his "failure to wait by vehicle." he will be charged an additional $250 . 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, punching holes in the bodywork, shattering the windows and detonating the airbag in the process. 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, but none the less got the boot off the front of the car (after which he angrily and psychotically hammers into the ground) leaving him relatively satisfied. His satisfaction soon disappears when he is forced to speed off to get his family after an enraged driver takes a potshot at him for holding up traffic.
Meanwhile, the rest of the family have had a wonderful time. They watch a Broadway musical and visit 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, While driving back to Springfield, the rest of the family reflect on their wonderful time in the city while Homer's antipathy towards New York is even worse. When Lisa asks if they can come back to New York, Homer's eye is twitching and he simply says "We'll see, honey. We'll see." as garbage flies from a truck and on to 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 currently airs uncut on Channel 11 (A sister channel of Channel Ten). 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.