Folks, we’ve got a weird episode to discuss today. It’s an incredibly complicated episode with several plot lines jumping around, and it sure is going to be a joy trying to keep this clear for you fine folks. Oh, and it starts off with a serious bummer, because this episode came out shortly after Marcia Wallace, longtime voice of Mrs. Krabapple had passed away, which is notified to us by a rather emotional chalkboard gag where they simply say they’ll miss Mrs. K. And then we’re given a real moment of silence, because the couch gag is a weird Hobbit parody, and it lasts approximately two hours.

Well, after that bummer the episode proper begins, and guess where we start? At a funeral! Not for Mrs. Krabappel though, it’s for some dude named Chip that we’ve never met, but who was apparently the greatest person in history. Everyone in Springfield is attending this funeral, and they’re all devastated at the loss of this Chip guy. The citizens of Springfield talk about their precious memories with Chip, but at the end Reverend Lovejoy does mention that even someone like Chip had some regrets in his life.

And this concept, that everyone has regrets, gets the people of Springfield thinking, and they begin pondering their own regrets in life. Which means we’re going to be getting a bunch of stories about people’s greatest failures! It all begins with Marge, because while everyone is standing around Patty and Selma point out that Marge should have a lot of regrets, mainly about Bart. And it really starts to bother Marge, because she becomes convinced that Bart has been screwed up, and it all stems from the fact that she used to listen to KISS records a bunch when she was pregnant. Sure, Marge. Let’s go with that.

It’s not just Marge though, because we then rapid-fire off a couple other regrets. We see that Kent Brockman is sad that he’s still just a local anchor instead of getting his own national news show like his old colleague Rachel Maddow. Homer thinks about the fact that in 2001 he decided to sell his Apple stock, right before the iPod changed the company forever, and he ended up buying an expensive bowling ball. And Mr. Burns is sad that he had a long lost love, but he doesn’t really want to talk to these peons about such a topic.

While everyone is standing around reminiscing about painful memories we see that Bart has started to prank the folks outside of the church, trying to get a fake tithe from them. And this really upsets Marge, who becomes convinced that he incessant KISS listening is what made him such a monster. And honestly, that’s really all this plot is going to be, Marge just being sad and Bart being an asshole, until he takes matters into his own hands.

What actually is interesting is Mr. Burns’ story though. Because we learn that not only did he have a long lost love, it was a beautiful French woman named Lilah, and the two had a torrid love affair in Paris between World War I and World War II. They were madly in love, and Burns wanted to marry Lilah, but she refused because Burns could never think of anyone but himself, and she just couldn’t live with someone like him. So Lilah left Burns, and he never saw her again. But now he wants to find her!

Meanwhile, Kent Brockman is very depressed about being stuck in Springfield, and it isn’t helped when Rachel Maddow shows up, seemingly just to mock him. We learn that they used to have a show together back when they were both starting out, but Kent wanted to take the easy route with everything and focus on infotainment. And it all came to a head when she wanted to expose a story about Krusty keeping a mountain of tires in the forest, and Kent just wanted to cover it up and accept a bribe from Krusty. This then caused a fracture between the two, and Maddow went on to have a legitimate news career while Kent Brockman witnessed the birth of the Tire Fire.

Things start to get a little random at this point in the episode, and we begin hopping around into all the plots. We see that Burns has found Lilah, and she’s shockingly become a Buddhist nun outside a mountain monastery in Springfield. Kent Brockman decides to go get a real news job, but ends up at Fox News. However, when learning that their secret technique to new is to just lie, he finds he actually has scruples and leaves. Homer is sad about his bowling ball, and is even more sad when he finds the store is closed now and he can’t get it shined. Oh, and Bart has decided to tie a bunch of balloons to a laundry hamper, hop in, and take to the skies!

Bart then begins a wild journey, travelling all around Springfield. And on that journey he passes by the mountaintop that Lilah is living in. Burns has recently arrived, and the two decide to rekindle their love affair by having some nun sex. However, while Burns is busy tinkering around in the bathroom with a bunch of old-timey prophylactics, Lilah ends up passing away of old age. Burns is pretty depressed, but he decides to do something to honor Lilah’s world-view, and goes to serve soup to poor people, thinking about someone other than himself for once.

That doesn’t help Bart though, who is still trapped up in his basket. And while he’s soaring around he passes the bus that Kent Brockman gets off, fresh from his trip to Fox News. Kent sees Bart, and realizes that he’s ratings gold, and goes to do an emergency broadcast about Bart. Which is how Marge learns about Bart’s predicament. She becomes terrified, and gets the police involved to help her save her son.

While Chief Wiggum is coming up with plans to rescue Bart, Marge continues to complain about KISS, and Wiggum actually brings her some solace by saying that he had Ralph listen to Mozart, and he didn’t turn out to be a genius. This helps Marge, but Bart is still trapped. Professor Frink then arrives, with a canon, saying that he has worked out the trajectory to save the day. And, luckily, Homer arrives with his bowling ball, which fits the cannon perfectly. They fire the ball into the air, it lands in Bart’s basket, and he’s dragged back down to Earth and safety. The town then apparently decides to never have regrets again.

I don’t know about this episode. In theory I think this should be an episode I like a whole lot. It’s similar to “22 Short Films about Springfield,” or “The Seemingly Never-Ending Story,” where we jump all around Springfield to check out a bunch of weird stories from some lesser seen characters. But none of these stories are overly engaging. Homer is complaining about a ball, Marge keeps talking about KISS, and Kent Brockman’s plot just kind of feels truncated. Honestly the Burns thing could have been interesting, but it’s so anemic and just feels completely half-baked. Normally these episode work, even though they have such frantic plots, but for some reason this one really came off as stitched together to me. It was somehow racing around while having not enough to say, just making a rather dull episode.

Take Away: We’ll miss you Mrs. K.

“Four Regrettings and a Funeral” was written by Marc Wilmore and directed by Mark Kirkland, 2013.