Welcome to Season Nine everyone! Woo! Nine seasons in! I’m not great at math, but I think I’m just about a third of the way through the project. Which, while that doesn’t seem like much, is a pretty ridiculous accomplishment. I’ve been doing this for eight months. So what do we have waiting for us to open up Season Nine? Oh…oh my. Huh. Well let’s dive on in to a truly awkward episode.

I had really forgotten how this story started. The whole scene with Duffman was crystallized in my memory, but this is one of those episodes where the first act and the rest of the episode just didn’t jive in my mind. And how it starts is with all the drunks showing up at Moe’s, right on time at five o’clock. And as the six of them prepare to get shit-faced just like every night, Moe announces that they are responsible for 91% of the traffic accidents in Springfield, so as a result one of them has to be a designated driver. And since none of them want to be the designated driver, Moe suggests they use the same method the Vatican uses to pick the Pope, and they have to reach into his jar of pickled eggs, and whoever grabs the black one has to stay sober. And the worst possible outcomes happens. Barney can’t drink the whole night.

And things go wrong almost immediately. The rest of the bar starts to get even drunker than normal, while Barney has to sit there, torturing himself and not drinking at all. Plus, just when things seem like they couldn’t be worse for Barney, something wonderful happens. Apparently Barney had sent in 10,000 Duff labels to the brewery, and as a reward they send over their corporate mascot Duffman, who is there to give Barney a dumpster full of beer and start a massive party in the bar. But Barney sticks to his guns, and remains sober, while the rest of the bar gets even more drunk. And in the end of the night, Barney drives everyone home, and drops Homer off at his house instead of taking him to the Lost City of Gold like he requested. But when Homer passes out in his doorway, Barney drives off. And doesn’t come back for two months.

So for two months Homer is carless, and Barney is nowhere to be seen. And just as he’s hanging fliers around town, Barney finally comes back in the trunk of a limo. He has no memory of the legendary bender that he’d gone on, and he has no idea where the car is. So Homer is still screwed. The logical thing to do at this point is for Homer to make his own car out of a mattress, but as he’s working on it he gets a serendipitous letter from the city of New York. Apparently Barney drove from wherever the hell Springfield is, all the way to New York, and left the car in Manhattan. And the city would like Homer to get rid of the car, because it’s illegally parked. So the family gets excited, thinking they get to go to Manhattan for a vacation, but Homer is less than thrilled. Turns out he went to New York when he was in college, and had a horrible time. Probably because it was the 70’s, and Manhattan was basically a dystopian wasteland in that decade. Homer tells the family about how he got his camera stolen, his luggage stolen by a cop, his wallet pickpocketed, his hotdog stolen by a bird, and garbage dumped on him by Woody Allen. All leading up to him getting in an altercation with a pimp, before getting attacked by the CHUDs in the sewer. But Marge tells Homer he’s being ridiculous, and announces that the family are going to take the bus to Manhattan and get the car back, since you can’t judge a place based on the “pimps and the CHUDs.”

So the family pile into a horrible bus, and take a monstrous trek across the country to the Big Apple. They roll into town, and we get the amazing scene where Bart mistakes a group of Hasidic Jewish men as ZZ Top, and tells them they rock. “Eh, maybe a little.” And as they get out of the bus station, Homer announces that he intends for the family to stay in the bus station, and just wait for him to come back. But Marge refuses and informs him that she and the kids are going to explore the town, and meet Homer in Central Park at sundown so they can head home. Homer is not really cool with that decision, but doesn’t argue. He then heads out to find his car. And where the car is parked is what gets us to the awkward part of this episode. He’s right between the Twin Towers of the World Trade Center.

Yep! Right in between the two towers. Oof. This episode came out in 1997, so of course they had no idea how uncomfortable a large portion of this episode was going to be in just a couple years, because how could they? Yeah, there are a lot of goofy things that the Simpsons have accidentally predicted, but they aren’t actually soothsayers. So let’s just try to put that aside, and focus on Homer’s goofy antics in World Trade Center Plaza. He gets to his car, and is baffled at the boot, which I guess isn’t a thing people in Springfield have. He starts looking through all the tickets piled up on the windshield, and calls the city’s traffic center, trying to get someone to come get the boot off. He has to wait there for Officer Grabowski, between 9am and 5pm, so he has a bit of a wait. And from here the episode starts to jump between Homer’s horrible time in the Plaza with the rest of the family’s magical day in New York.

Let’s start with the family. They start riding the subway while Bart tries to grift people out of money by licking handrails, and Lisa befriends a crazy homeless guy. They then start hitting all of the big tourist destinations, like all small town rubes. First they make it to Chinatown where Bart sets off a bunch of fireworks while Lisa is aghast at the rabbits who are sleeping upside down, and inside out. Next up the ladies check out some amazing designer shoes while Bart wanders off and finds the offices of Mad Magazine, which appear to be pretty bland, until he finds out that Alfred E Neuman is real and runs the place with all the other goofy comic characters from the magazine. And after that they hit up a Broadway show, the hilarious “Kickin’ It,” a musical journey through the Betty Ford Center. Which is just genius guys. The Simpsons have made a lot of fake musicals over the years, but I think Kickin’ It may be the funniest. Plus I love that there’s a lady behind Marge who can’t see around her hair.

But while all of this is going on, Homer’s having a pretty nightmarish time in the Plaza. He waits around for the officer, trying to find something to do, and ends up getting some spare change from passersby, who assume he’s a bum. And after a while Homer goes with it, and realizes he’s made enough money to get some pizza. And since its New York there’s a pizza parlor right across the street. But he can’t leave his car, and since he can’t stretch his arms a whole block, he ends up having to eat some street meat called Khlav Kalash from an awkward Middle Eastern guy who doesn’t speak much English. Khlav Kalash sadly isn’t a real food, but it looks terrible. However Homer chokes down some, and ends up drinking a bunch of crab juice, since it’s a better alternative than Mountain Dew. But after all the crab juice he finds he needs to pee, but still can’t leave. Which is a conundrum.

Homer asks the Khlav Kalash guy if he has a bathroom in his cart, and finds that the nearest one is at the observation deck of the Tower. Which doesn’t seem accurate, but whatever. So after a lot of internal debate, and an attempt to pee in a mailbox, he decides he has no choice, and heads off to the top of the Tower. And after taking forever, he gets there and finds that that bathroom is temporarily closed, and he has to go to the other Tower. So he zips down and up the next tower, and is able to have the most satisfying pee in the world. Unfortunately, as he’s peeing, he glances down at his car, and finds that he’s misses Officer Grabowski, gaining yet another ticket.

Homer gets down to his car, furious that he’s been screwed over yet again by New York. And as he’s wandering around swearing, he realizes that his worst dream is about to occur. The sun is going down, and all the weirdos are about to come out, since Homer apparently thinks that New York is like the Warriors. So with this new urgency, Homer decides to do something drastic, and starts revving his car until he’s able to drive with the boot, even though it just destroys more of his car. But who cares, he’s moving! Slowly. So after a little bit of journeying through the city, Homer pulls over and get a hold of a jackhammer to try and get the boot off. And after destroying a lot of his car, he succeeds! So Homer races off to Central Park, and after a brief chase with a carriage that the rest of the family are riding in, they all pile into the car and head home to Springfield. And the episode ends as the family fondly remembers their wonderful trip to New York, as Homer deals with medical waste flying into his face thanks to his missing windshield.

This episode…is challenging. I remember the four years in between its airing and the September 11^th terrorist attacks that this was a hilarious episode. The Khlav Kalash guy, Homer’s pee woes, the carriage race, the family wandering around the town, this episode is really great. It’s basically an episode like “Bart vs. Australia,” where it’s just the Simpsons going on vacation and experiencing a new location while making fun of the stereotypes the city has. And it’s a really solid example of that kind of episode. The problem is, it’s pretty much impossible to watch it without thinking about the attacks, and the fact that Homer is running around in two buildings which don’t exist anymore. Yeah, there’s some specific moments like the line “they stick all the jerks in Tower One,” which really don’t feel right any more, but by and large it’s just a feeling of awkwardness that lingers over the whole episode. Plus there’s all the idiots that misconstrue the human mind’s ability to find patterns with the Simpsons somehow being able to predict the future, like when Bart holds up the flyer that says the bus fare is $9, while the Twin Towers are right next to it, making a nice like 9/11. Yeah, that’s weird, but there are a lot of weird Trade Center things that dumb people think are coded messages. That stuff is stupid, but there still is some awkwardness in this episode. If you can somehow watch the episode and divorce yourself from the real world horrors, this is a hilarious episode with some great scenes, it’s just a little difficult since the episode got ruined by one of the most recognizable and jointly shared moments in history.

Take Away: The Simpsons can’t predict the future. And everything seems bad if you focus of the pimps and the CHUDs.

“The City of New York vs. Homer Simpson” was written by Ian Maxtone-Graham and directed by Jim Reardon, 1997.