Lifetime of Simpsons

S28 E14 – The Cad and the Hat



Well, we’ve made it through another weird-as-hell week here, folks. And, what better way to celebrate that than with an episode where Bart has to deal with the horrible ramifications of crushing guilt? You know, a light topic to end the week on.

The episode begins with an odd little moment where Bart and Lisa are dressed up and telling us that they’re going to be telling us a story where they didn’t get a long, but learned to put their differences aside. I’m sure that this is a reference to something, but it’s not something I was familiar with, and the bit of research I did wasn’t able to dig something up. So, we’ll just chock that up to a fault in my reference base and move along.

After that we learn that Springfield is going through the hottest summer on record, and people are losing their goddamn minds. So, to curb the people of Springfield’s natural inclination to chaos, Mayor Quimby decides to lower some health standards so that they can reopen their beaches for citizens to use. Which of course causes a flood of townsfolk to rush to the beach, and the Simpsons are among them, because of course they are.

We get to see the Simpsons frolicking around on the beach, and specifically see Bart and Lisa getting along, pulling pranks on Homer. However, at some point they head into some little shops on the pier, and are both allowed to get something. Lisa finds an adorable little hat that she immediately falls in love with, and Bart gets a temporary tattoo that says “Bad to the Bone,” which promises to be water-proof.

Unfortunately, as soon as Bart gets back in the water his tattoo washes off, and he gets incredibly mad. And, to focus that anger, he starts to become very resentful of Lisa’s hat, because she’s getting to keep it and everyone starts complimenting it on her. So, clearly, Bart is going to be doing something horrible to that hat.

But, before we see what he does to the hat, we need to set up a B-Plot. It begins with Marge getting irritated that Homer is ogling the beach-volleyball players, and decides to force him to watch the old people playing chess instead. And, surprisingly, Homer gets really into it. In fact, he gets so interested that Jasper invites him to play a game, assuming he’ll kick his ass. However, Homer ends up winning. Quite handily. Because, apparently, Homer is a chess prodigy, and he used to play a lot with Abe, and this is something that he knows, and has just never chosen to inform any of us about.


Now that that ball’s in motion though, let’s get back to the main plot. Because that night as the Simpsons are leaving the beach and heading home, they of course make a pitstop for Homer to get an absurd amount of Krusty Burger. And, while waiting for the food, Bart notices that a) Lisa has fallen asleep, b) her hat is in between them, and c) there’s a junkyard next door to the Krusty Burger. So, putting them all together, Bart grabs the hat, throws it out the window, and tosses it into the junkyard.

However, that night Bart starts to notice that he’s having trouble sleeping. He’s not quite sure why, and as he’s trying to figure that out he’s suddenly visited by a little creature that looks kind of like him. The creature introduces itself as a manifestation of Bart’s guilt. But, not surprisingly, Bart doesn’t think that he did anything wrong, and does his best to ignore Guilt and get some sleep. But, the more he ignores his Guilt, the bigger and uglier it gets.

Meanwhile, Lisa wakes up in the middle of the night and realizes that she doesn’t have her hat. So, she races downstairs and outside to look for it in the car. Unfortunately, she only finds Krusty Burger detritus, and no hat. She then does something incredibly weird, and rides her bike all the way out to the pier again, only to find that Shauna is closing up the shop where they bought the hat. Lisa asks her if they have another one, and Shauna tells her that they’re sold out and don’t plan on getting more. The hat is gone forever.

The next morning the hat plot continues, but we also keep checking in on Homer. Because now that it’s been revealed that he’s a chess master, he decides to start showing off. He plays against the guys at the bar, and is able to beat them all handily. He then gives us some backstory. Apparently Homer and Abe played all the time after Mona left, and Abe always trounced him. So, Homer met a grandmaster and started taking lessons with him until he was finally skilled enough to beat Abe. However, before they could finish a game where Homer was clearly going to win, Abe throws a fit, stops the game, and never plays with him again.

And while all of that’s going on, we see that Lisa is growing increasingly sad that her hat is missing, all while Bart is ignoring his increasingly growing Guilt. He seems pretty convinced that he can keep ignoring Guilt, but eventually that breaks down, and that evening he decides to tell Lisa the truth. And, not surprisingly, she doesn’t forgive him. She’s furious, and Bart realizes that even though he came clean, the Guilt is still there.


Bart’s guilt is continuing to grow, becoming a massive and abusive monster. He knows that the only way to conquer the Guilt is to get Lisa to forgive him, so he decides to try and get the hat back for her. He heads over to the junkyard where he trashed the hat, and luckily finds it sitting atop a car. But, as soon as he does that, the car is smashed into a cube, and the hat is seemingly trapped inside, never to be retrieved.

Meanwhile, Moe has been poking around on reddit, something that never ends well, and he ends up finding out that Homer’s chess skill apparently represent a desire to destroy Abe. Homer decides this makes a whole lot of sense, and chooses to destroy all of his chess pieces rather than deal with all of the emotions that this revelation is stirring up. However, Marge thinks that this is a bad call, and does something kind of strange.

She gets in contact with grandmaster Magnus Carlson, and he gives Homer a Skype call where he tells Homer that he needs to keep perusing chess, and the only way to get past his feelings is to challenge Abe to a real match, and beat him. So, Homer calls Abe up, and they start playing a game of chess to prove once and for all who is the best. They keep trying to psych each other out, but it becomes clear that Homer is about to win. Which is when he does something surprising. He surrenders. Homer decides that he doesn’t need to crush Abe, and prefers to leave this question unanswered and keep a decent relationship with him.

Speaking of relationships, Bart is still in that junkyard, trying to figure out how to get the hat out of the cube. He can’t really see any way out of this, but does find something miraculous out. His Buzz soda eats through the metal of the car. So, Bart comes up with an elaborate plan where he fills a kiddie pool with soda, brings Rod and Todd in to perform a miracle and get God to lift the cube up, they drop it into the soda, and it eats away the car until the hat is freed. Bart then gets the hat, and brings it back to Lisa. She at first still doesn’t want to forgive him, but eventually decides that he’s at least trying, and she forgives him. Bart’s Guilt then fades away, and everything goes back to normal.


This episode is fine. There’s really not much to it that elevates it above fine, but it works alright. We’ve seen much better episodes revolving around Bart and Lisa’s relationship, and even better episodes about Bart having to come to terms with his guilt surrounding doing something bad to Lisa. Yeah, I do think that this episode’s weird manifestation of Guilt is kind of interesting, but even that kind of fades away after a while, basically once Bart gets to the junkyard and things get completely ridiculous. It’s heart’s in the right place, and there’s some good emotional stuff in here, it just feels like it’s all things we’ve seen before. Honestly, the ‘Homer knows chess know’ stuff is the best part of the episode, and even then it’s not anything completely mind-blowing. It’s just kind of fun. But, considering the way we started this week out, “kind of fun” isn’t a bad way to close the week out.

Take Away: Don’t just be motivated by guilt when you do shitty things, be motivated by the fact that you hurt someone.


“The Cad and the Hat” was written by Ron Zimmerman and directed by Steven Dean Moore, 2017.



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