5 Funny “The Simpsons” Episodes About Gambling

The Simpsons gambling image
The Simpsons. Image Credit: Shutterstock

The Simpsons are one of the best-loved cartoons ever produced, especially if you grew up in the 90s, with a few episodes dedicated to the topic of gambling.

Since it first aired in December 1989, The Simpsons has evolved to become one of the most-watched cartoons ever.  Today, our peculiar, yellow-skinned family continues to be an all-time favourite animation for young and old alike. But besides all the laughter, the show has also featured some friskier and riskier topics, including drugs, infidelity, organised crime, and even gambling! 

Here are a few episodes of The Simpsons that touch on the topic of gambling:

1. The President Wore Pearls (Season 15)

In the most unusual setting ever, Springfield Elementary decides to hold a casino fundraiser. Martin Prince is the evening’s host and the student president, and when Homer scores big on a game, he is informed that he can only redeem his jackpot in exchange for a meal voucher.

When other patrons realise that they can’t win any real money, the school stoops into chaos, and rioting breaks out. Martin is sacked from his position and new elections are held, with Lisa scooping all the ballots. She becomes a vocal advocate for the students, but it’s not long before fresh challenges arise, and the school’s only solution is to fire her too.

2. $pringfield (Season 5)

$pringfield, or “How I Learned to Stop Worrying and Love Legalised Gambling,” is an episode revolving around Springfield’s impending economic slump. In a bid to reverse the financial hardship, gambling is legalised, and Homer gets the job of a blackjack dealer in Mr Burns’ Casino.

Simultaneously, Bart opens his own casino, Marge develops a slots addiction, Barney becomes a coin dispenser, and Maggie nearly ends up as food for the tigers! The storyline features some hilarious guest appearances by Robert Goulet and Gerry Cooney. The episode is a great salute to the 1964 Stanley Kubrick classic, Dr Strangelove: How I Learned to Stop Worrying and Love the Bomb.

3. The Telltale Head (Season 1)

Following Homer’s advice, while he is absorbed in sports betting on a football game, Bart tries to gain popularity amongst the local bullies by decapitating the head of a statue. Unfortunately, the head happens to belong to the beloved town founder, Jebediah Springfield. Needless to say, the act doesn’t go down too well with the bullies, and matter backfires very quickly when locals learn of the crime.

Once an angry crowd is formed to discover the culprit, Bart owns up and touches people’s hearts when he returns the head. Although the act brings the community closer together, Homer blames himself for giving Bart poor advice in the first place. Luckily, both are forgiven, and the mob disperses for another episode!

4. Sky Police (Season 26)

After the local church becomes damaged from a jetpack accident, Marge gathers the congregation and organises to raise funds for the necessary repairs. However, contrary to the biblical teachings, they end up getting to their goal by learning how to count cards. With Apu as the swindling ringleader, the group wins wads of moolah at the local gambling house.

After they strike the jackpot, Homer is taken captive by the casino staff, who demand that he returns the money. When he informs them that it’s already gone to the church’s contractor, they threaten him with physical violence.

5. Lisa with an “S” (Season 27)

The plot begins with Homer taking part in a poker game at Moe’s with Lenny, Barney, and Carl. Prior to this, Homer assures Lisa that, should he win, he’ll pay her enrolment at a top-notch band camp she always wanted to attend. He ends up losing the $5,000 stake to Laney Fontaine, a Broadway icon. Homer then tries to coerce Laney to give him back the money by inviting her for dinner at the Simpson residence.

It’s here that Laney and Lisa get acquainted, and Lisa is recognised for her saxophone playing skills. As a result, Lisa jets off with Laney to New York to perform shows there for a month. But Marge soon begins yearning for her daughter, and the entire family flies to the Big Apple to persuade her to come back.

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