Introducing legalised gambling is an all-time great concept for this show to play with. If The Simpsons’ strengths can be distilled down to a few elements, it would be the knack for absurdity, the big heart, the satirical view of the world, and the strength of its worldbuilding, and bringing in the casino allows it to start broad, looking at why the town as a whole brings it in and how its affected, and then zooming in on our title characters. It’s another quick-fix solution that feels good, has awful consequences, and fuels Mr Burns’ monopoly, though it’s interesting to me that the show concedes that it’ll succeed at bringing more money in the town, including putting that perspective in Marge’s mouth.

The unifying premise actually allows the episode to branch off into more than just an A-plot and B-plot – there’s Marge’s addiction to gambling, Homer becoming a blackjack dealer, Bart making his own casino, and Burns descending into Howard Hughes madness. By holding obsessively to a setup-punchline approach to comedy, The Simpsons allows itself to make up its own storytelling rules, which creates a really organic feeling where a story can either hold to one central idea or branch off into more directions if it so chooses. In fact, I would say this episode shows four different perspectives on the same thing.

Marge’s story has the strongest emotional beats, which makes it what I would think of as the A-plot. It’s something that almost hits too hard – Marge, as the archetypal Mother, absolutely would play the slots, and her descent into addiction is just barely cartoony; the joke about Smithers putting in the barest minimal effort to address her clear addiction certainly matches my experiences and observations of the gambling industry, the same way the show delved into the alcohol industry. Why would these industries work hard to fight something they are trying to make money off (notice companies working to address sexism in their industries now that consumers are making it clear they won’t support them otherwise)?

Bart would absolutely be fascinated by the glitz and glamour of a casino; I always get a kick out of kid versions of adult things, and he absolutely would make his own casino and have tremendous fun doing it – love that the treehouse magically becomes four times bigger on the inside. Bart is always fascinated by semi-classy Hefner-esque style (like his dressing gown/bubble pipe combo), and this seems like a perfect combo of that love with his prank-style intelligence and his sense of showmanship. Also, it’s good fun seeing him con Robert Goulet into singing “Jingle Bells, Batman Smells”.

(Mr Burns jumps all the way to the other end of the scale, the guy right at the top of the empire. I suppose you could read it as showing how success warps people, but really I just take it as a funny bunch of riffs on the legend of Howard Hughes.)

Homer starts out in his own story, working as a blackjack dealer and delivering the edgy competence he brings to his day job, before getting subsumed into Marge’s story when he’s forced to step up and bring that edgy competence to his parenting, in order to show what Marge’s addiction means to the family. I could see how someone might find Homer’s incompetence unsympathetic here (though his attempt to cook a pie out of the few elements he has is an all time great joke – “Let’s go see Mom.”), but not only does it contain one of my favourite serious Homer moments, that moment is also one of the funniest Simpsons moments:

“No, Lisa. The only monster here is the gambling monster that has enslaved your mother. I call him Gamblor, and it’s time to snatch your mother from his neon claws!”

I have a deep love for stories that shoot for what I like to call ‘the ridiculous and the sublime’, hitting emotional beats that are as profound as they are silly. This joke is so many parts of the Simpsons ethos at once; for one thing, not only does it create absurdity by pushing the logic we’re presented with, it does it twice. For another, it’s such a rich character moment – the line starts out something you would fairly typically hear in this context on TV, but only Homer would go to the effort to give said monster a name, and even if someone did think to do that, they probably wouldn’t give it such a lazy name. And, as ever, Castellanetta puts so much sincerity in the line; outraged, heartbroken, and building up to a frothing frenzy.

The show ends with Marge not solving her gambling addiction, because the show recognises that you can’t really solve a problem like that in twenty minutes of airtime, but with Marge acknowledging her addiction, which feel appropriate. If this were a serialised show, that would be a good jumping off point for a longer story, but we’ll have to settle here; sadly, this is the limitation of this kind of episodic storytelling, although I think it works for what it is.

Chalkboard Gag: I will not say “Springfield” just to get applause
Couch Gag: The family collide and shatter while the dog looks on.

This episode was written by Bill Oakley and Josh Weinstein and directed by Wes Archer. The episode was inspired both by a newspaper article on a town that was introducing gambling, and by the desire to really explore what a crummy town Springfield is, which obviously worked out well. Archer was pleased with how the casino lights turned out, which is another example of the crew’s high standards. There was a short time where there was a subplot on Planet Hollywood in an attempt to capitalise on a deal that would have landed Arnold Schwarzenegger, Bruce Willis, and Sylvester Stallone as guest stars, which fell through.

Gerry Cooney and Robert Goulet guest star as themselves, and Mirkin described Goulet as a lot of fun and very willing to poke fun at himself.

One of my favourite minor recurring jokes is crowds applauding ridiculous things; Barney’s burp must be the purest essence of this joke.

The title is a reference to Dr Strangelove, or How I Learned to Stop Worrying and Love the Bomb. Burns’ bed resembles one from 2001: A Space Odyssey. Two characters at the casino are parodies of the leads from Rain Man. Homer’s lifelong dream this episode was to appear on The Gong Show. As said, Burns is a parody of Howard Hughes. Homer references The Wizard of Oz.

First Appearances: Gunter and Ernst, the Rich Texan.

Iconic Moments: “That’s a right triangle, ya idiot!” | “What was I laughing about? Oh yes, that crippled Irishman!” | “I have a photographic memory!” | The shot of Homer when he says “Bart, I don’t want to alarm you,” has become a popular reaction image for conveying overthinking in a lighthearted manner. | “I said hop in.”
Biggest Laugh: