On the cover of the magazine, the text says "New York $9", the Twin Towers look like the number 11. So ironically it shows the numbers 9 and 11 and this episode aired 4 years before the September 11 attacks.
After the September 11 attacks, the episode was banned from television due to the prominence of the World Trade Center towers. After a few years, the episode came back, though some airings banned all the scenes of Homer near the Twin Towers (including his bathroom rush to both towers) or left them in and cut out the line, "They stick all the jerks in Tower One." This is particularly sensitive because in 1993, Tower One (the North Tower) was the site of the initial bombing, and in the 2001 attacks, Tower One was the first to be hit and the tower where more people were killed or trapped.
A clip from this episode are also shown in the 2000 movie The Beach.
The writers on the DVD commentary have mentioned how dated this episode has become following 9/11, and regret using the "jerks in Tower One" line.
In this episode a New York civilian tosses a coin in front of Homer, leaving Homer to respond, "I'm not a bum." However, the subplot of Milhouse Doesn't Live Here Anymore revolves around Homer posing as a bum which he proves to be so good at that he steals attention from real bums.
Marge tells Homer they will meet in Central Park. However, it is 843 acres big so there are many places where they can meet.
The South Tower's indoor observation deck is on the 107th floor.
Jurassic Park - The way the bowl of peanuts starts to vibrate as the Duffmobile approaches references the 1993 film, particularly the cup of water vibrating when the Tyrannosaurus Rex approaches.
When Bart, Marge, and Lisa are on the subway an ad can be seen that says "Can you throw a football? Become a New York Jet. Call 1-800-4NYJETS." This is a reference to the New York Jets, who had the worst season in franchise history the year before this episode came out, with a 1–15 record. The year this episode came out the Jets went 9–7.
When Duffman first arrives at Moe's Tavern, he hands several people cans of beer from his utility belt. In the very next shot, after Barney tells Duffman that he's the designated driver and cannot claim his free bottomless mug of Duff, Duffman's belt is still completely stocked with cans.
Homer tapes a number of homemade signs to both front windows of Moe's Tavern requesting information about the car Barney drove off with, in the shot immediately after Barney is dropped off by the chauffeur not only are the signs gone from the window, but Moe's only has one front window.
The amount of damage of the windows and headlights on Homer's car changes innumerable times between shots.
The car's headlights are destroyed while Homer tries to get the car boot off his car using a jackhammer; however, during the credits as the screen pans away from Homer's car showing the Brooklyn Bridge, the headlights are shown intact.
An outside mirror reappears and disappears from Homer's car between shots.
Homer's wristwatch reappears and disappears during scenes where he has to call and wait for the officer.
When Homer attempts to leave without his getting his car towed away, his car door he opens has no window or door post. But when he first stops to get his car boot off, the car door now has changed with a window and a door post present.
As Homer is infuriated by the radio tunes playing, he kicks and breaks the radio. But when he's trying to get his car boot off, the radio (shown from an inside view of the car) has fixed itself.
When the original World Trade Center was still around, the North Tower had a 360 ft. tall TV antenna on the center of its roof which was installed in 1978. However, at the moment when Homer discovers the restroom to be out of order in the South Tower's indoor observation deck, he rushes himself over to the North Tower where it is noticeably missing. It's worth noting because all other shots of the roof in this episode show it.
Homer should have called the police because Barney stole his car, as borrowing something and failing to return it is considered a form of theft.