So far there haven’t been that many episodes that suffer from being made so long ago. The Simpsons generally have a pretty timeless quality about it that makes these stories work great at any point that you’re watching it. Yeah, sometimes the guest stars are a little odd, and need to be looked at in context to understand, but generally the show can really exist in any time. Then there’s this episode, the most mid-90s episode I’ve seen so far.

Things start off with a hilarious joke where Otto is getting an award for excellence in safety, only to have that be revealed as a dream. Because of course Otto isn’t getting safety awards, he’s too busy sleeping while driving a bus full of kids! Otto freaks out when Milhouse wakes him up, but is unable to keep the bus from flying into a junk yard where the bus is then crushed in a compactor. And after that little “unscheduled field trip,” the school announces that parents have to figure out a car-pool situation until a new bus can be brought in.

So lucky Homer gets to be a carpool leader and starts bringing Bart, Lisa, Nelson, Milhouse, and Janey to school. And almost immediately Homer starts being a typical dad, and weirding out all of the kids while embarrassing Bart and Lisa. He listens to classic rock while teaching the kids about “jive” and how you need to say the word jive with a lot of sass, much to the shame of everyone. And when it’s revealed that the kids don’t know who or what Grand Funk Railroad is, Homer loses it. He tries to educate the kids on real music, but they have no interest in that, and just run away as soon as they get to school, ignoring him. And this, coupled with Bart telling Homer that he’s out of touch and lame, causes Homer to do something that makes anyone feel old and sad; he goes to investigate contemporary music.

This leads Homer to a record store which is called Suicide Notes (formerly Good Vibrations) and Homer is shocked to learn that he doesn’t recognize any of the bands that are being sold. I’ll tell you, it’s a whole lot of fun to talk about current indie bands with my older co-workers, and see them struggle to figure out if I’m making up Trampled by Turtles, or it it’s a real band. And while talking to the cynical, detached teenager who is working at the record store, he learns about the hip new music festival that’s getting ready to come to Springfield, Hullabalooza. Which itself is a reference that I had to think about, trying to remember that Lollapalooza was a thing. Homer then tries to explain to the clerk that rock attained perfection in 1974, and that things shouldn’t have changed… which I kind of agree with.

But the trip to the record store leads Homer to start thinking about how he used to be cool, and we’re treated to an amazing flashback visual gag where we see some cool Dazed and Confused looking dudes setting up their strobe light in their awesome van, while Homer slowly gets closer and closer in the strobes, before shooting way far away. There’s also the great line from Grandpa when they make fun of him for not being cool anymore, which is an amazingly true statement: “I used to be with it, until they changed what it was. Now what I am with isn’t it, and what is it seems weird and scary to me. It’ll happen to you!” And this makes Homer realize that he needs to do something to cement his coolness, and reconnect with his youth. So the next day he piles Bart and Lisa into the car, but instead of going to school he announces that he got tickets to Hullabalooza for them. So Homer becomes a real amazing father and lets his kids skip school to be around a bunch of stoned teenagers!

The three get to the fairgrounds and start experiencing the weirdness of the festival. They watch a freakshow, learn that a lost child will become the property of Blockbuster if not claimed, and the kids are introduced to the smell of marijuana, which they describe as smelling like “Otto’s jacket.” But while Bart and Lisa are having a good time, things aren’t doing great for Homer. He got a Rasta hat and is walking around being called a narc by everyone, and after getting a lot of people pissed off at him while Smashing Pumpkins play Homer gets thrown out of the crowd, shunned for his lameness. But when Homer wanders off, sad that no one likes him, he ends up kicking a cannon that fires a balloon pig out of it, right into his gut. The roadies, and Peter Frampton, are worried that Homer damaged the pig, and are shocked that Homer barely seems fazed by the hit.

And that particular skill-set really appeals to the freakshow manager, so he offers Homer a job to travel around the country with the festival and get shot in the gut with cannonballs. Marge is obviously not down with this career choice, but that apparently doesn’t matter because Homer quickly starts heading out with the festival while becoming increasingly popular. People are loving him, specifically coming out to see him and even the sullen teenager like him:

Teen 1: “Oh here comes the cannonball guy. He’s cool.”

Teen 2: “Are you being sarcastic, dude?”

Teen1: “I don’t even know anymore.”

And not only are the crowds liking him, but so are the bands. He makes friends with the Smashing Pumpkins, Peter Frampton, Sonic Youth, and Cypress Hill while struggling to figure out their music. He even bonds with the Pumpkins over his being kicked out of AV club for his views on Vietnam, and stealing projectors.

But things start to go wrong when Homer’s stomach starts to make these incredibly strange noises. And since the freakshow manager gets worried, he sends Homer to a vet to get checked out. The vet gives him an examination, and finds that his stomach is destroyed, and one more cannonball could easily kill him. But Homer refuses to do anything about this, and says that he’ll still go ahead and get shot with cannonballs for a living, especially since the tour is coming back to Springfield soon. And his drive to still get shot strengthens when he get home and finds that Bart is super proud of him, and is even writing a paper about how Homer’s his hero. So even though he’s worried about the stomach, he still goes through with it.

The family then go to Hullabalooza where Homer gets them all back stage so they can see Cypress Hill struggle to remember if they ordered the London Symphony Orchestra to perform with them while high. We then see the town enjoy the concert while learning that Mr. Burns owns Ticketmaster, and that Sonic Youth have no problem stealing food from Peter Frampton. But after some music gags we see the real plot where Homer walks out to get shot, and the crowd goes nuts. The canon is then loaded, and right as it’s fired he dives out of the way, treasuring his safety over fame. Everyone in the crowd begins booing Homer, but he doesn’t care because he’s safe with his family. The freakshow manager fires Homer, and he goes back to his life while Bart and Lisa have immediately lost respect for Homer, and tells Homer and Marge just how uncool they are on their way home.

This is a weird episode. It’s one of the episodes like “Homer at Bat” that really exists more to show off their bounty of guest stars than anything else, and those episodes tend to either work great, or fail. And this one kind of fails. There’s some good gags in the episode, but it’s such a weird premise, and the bands were all so of that time that the episode has really aged poorly. So many detached, cynical teenagers in this episode. It just feels weird, and I had to really think about that time period for things to make sense, which isn’t something you have to do with other classic episodes. Really the only thing that holds up for me in this episode is Homer’s existential horror that he’s uncool, and that pop culture has moved on without him, because man is that a realistic problem that when you’re a kid seems ridiculous, but the closer you get to forty becomes a shocking reality.

Take Away: Teenagers suck, and what’s “it” will leave you long behind.

“Homerpalooza” was written by Brent Forrester and directed by Was Archer, 1996.