Top 10 gambling scenes from The Simpsons

Now well into its third decade on the air, The Simpsons has covered just about every topic under the sun. Religion, relationships, sex, fame, politics, sports, music, food, alcohol, drugs, technology, capitalism, organised crime, space travel, animal cruelty, gay culture – whatever you can dream up, they’ve done it.

Gambling is no exception. From whole storylines to one-line gags, betting and gaming culture has set the scene for some of the show’s most memorable moments. Thus, we thought it might be fun to dig up some of our favourite gambling-related episodes, scenes, quotes and jokes from television’s longest-running animated comedy.

10. Santa’s Little Helper

“Simpsons Roasting on an Open Fire”
Season 1, Episode 1

That’s right – gambling featured in the very first Simpsons episode to ever grace the airwaves. The 1989 Christmas special centres around the family’s financial troubles, with Homer taking on a second job as a shopping mall Santa to try and make ends meet. Money remains tight, however, so he heads to the Springfield Downs greyhound track and bets everything he has on a plucky outsider named Santa’s Little Helper. The dog runs last, but Homer’s failed wager becomes a source of Christmas joy as the Simpson family gains a new member.

9. Marge and Co. learn to count cards

“Sky Police”
Season 26, Episode 16

From the oldest episode in the Simpsons catalogue, we now fast forward to one of the newest. When Chief Wiggum’s rogue jetpack wrecks the church, members of the congregation turn to gambling in order to raise funds for repairs. Apu teaches Marge and a motley crew featuring Agnes Skinner, Sideshow Mel, Ned Flanders and the Lovejoys to count cards as a group a la the famous MIT team, as dramatised in the movie ’21’.

8. Krusty bets his daughter’s violin

“Insane Clown Poppy”
Season 12, Episode 3

It wasn’t the most popular episode of the 12th series, but Homer’s presence makes this one of the more memorable of the show’s many poker-related scenes. Having already lost all his cash and a Rolex watch to the Springfield mob boss Fat Tony, Krusty the Clown wagers his newfound daughter’s prized possession, a violin, on four Aces with a King kicker. It doesn’t end well.

7. Bart’s roulette fantasy

“‘Round Springfield”
Season 6, Episode 22

While Lisa bids a sad farewell to Bleeding Gums Murphy, her brother becomes entangled in a law suit after ingesting a rather harmful piece of Krusty-brand breakfast cereal. He wins $100,000 in damages, but the ever-shifty Lionel Hutz claims the majority of the payout for “legal fees”. Bart doesn’t register the scam, however, and daydreams about spending his $500 on a single spin at the roulette table. It’s a simple gag, but a classic.

6. Krusty bets against the Harlem Globetrotters

“Homie the Clown”
Season 6, Episode 15

Krusty is forced to open up a clown college after his gambling habit leads him to the brink of bankruptcy. In an attempt to wipe clean his slate with the Springfield mafia, he makes an all-or-nothing wager on the Washington Generals. Krusty’s accountant is gobsmacked, while the clown himself is exasperated by the Harlem Globetrotters’ questionable tactics: “That game was fixed! They were using a freakin’ ladder, for God’s sakes!”

5. Homer’s roulette masterclass

“Viva Ned Flanders”
Season 10, Episode 10

After questioning whether his piety has caused him to miss out on life’s myriad pleasures, Ned Flanders agrees to join Homer on a spur-of-the-moment trip to Las Vegas. They visit the casino floor at Nero’s Palace, where Homer shows off his method for picking roulette numbers. Ned unwittingly contributes a winner and is persuaded to have a modest flutter himself, but his next-door neighbour has other ideas.

4. Lisa helps Homer bet on football games

“Lisa the Greek”
Season 3, Episode 14

Betting and gaming has come up dozens of times throughout The Simpsons‘ 20-odd years on the air, but this was the first time it explored the topic in depth. In an attempt to connect with her father, Lisa helps the hapless Homer – a sucker for a bet – pick the winners for Sunday football matches. If the stories are to be believed, the episode came about because the show’s staffers were obsessed with NFL and Super Bowl betting.

3. Homer’s foolproof blackjack strategy

“Brother from the Same Planet”
Season 4, Episode 14

After Homer forgets to pick up his son from soccer practice, the disillusioned Bart seeks out a more reliable role model via The Bigger Brothers – a mentor program for orphans and disadvantaged children. When his new father figure, Tom, asks about his real dad, Bart conjures a tale of a man who squandered his family’s life savings on a single hand of blackjack. The faux flashback only lasts about five seconds, but it’s one of the best gags in all of the fourth season.

2. Homer is a little slow… but great at poker

“Secrets of a Successful Marriage”
Season 5, Episode 22

The Simpsons has churned out plenty of poker scenes over the years, but this is the absolute cream of the crop. Playing with Carl, Lenny and Moe, the clueless Homer – after choking on an apparently inedible poker chip – unwittingly flukes the pot with a straight flush. His reaction (or lack thereof) after being called “a little slow” has become one of the most quoted bits in the show’s entire run.

1. Mr. Burns’ Casino

“$pringfield (or, How I Learned to Stop Worrying and Legalize Gambling)”
Season 5, Episode 10

Hilarious, poignant and endlessly quotable, “$pringfield” ranks among the great all-round Simpsons episodes of the 1990s. It’s almost impossible to pick a favourite joke, line, or scene. Homer’s woeful ineptitude as a casino dealer tickles the ribs on numerous occasions, as do his futile attempts to keep the family functioning when Marge becomes hooked on the pokies. Bart starts his own casino, with amusing results, while Mr. Burns develops a nasty case of Howard Hughes syndrome.

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