Spanning over three decades on television, The Simpsons is a series known for many things. On top of its trademark take on life in Middle America and an astonishing number of times it has correctly predicted the future, the show is also known for fantastic musical numbers.

The Simpsons has actually been nominated for an Emmy nine times in the Outstanding Music and Lyrics category, winning twice. And on top of original songs, the show has lampooned famous tunes and paid homage to classic musicals on numerous occasions. From a song about the best little whorehouse in Springfield to an epic duet between Lisa and Bleeding Gums Murphy, here are the best musical numbers in The Simpsons‘ history.

10. H.M.S. Pinafore

In the season 5 episode Cape Feare, Sideshow Bob (voiced by Kelsey Grammer) is once again after Bart. Toward the end of the episode, the two find themselves on a boat drifting down a river toward Springfield. Bart, realizing he needs to stall for time before they arrive in town, asks Sideshow Bob for a simple request before being killed: to sing the entire score of the 1878 English opera H.M.S. Pinafore.

Bob, being the theater lover that he is, obviously can’t refuse. What starts as Sideshow Bob singing a capella turns into a whole production filled with costumes, an orchestra, its own Playbill, and one song where Bart even joins in for a duet. It’s one of those classic Simpsons moments that was perfectly absurd while also being totally on brand for the characters, making it feel real and hilarious.

9. Jazzman

One of the most touching musical numbers in The Simpsons came in season 6’s ‘Round Springfield. In the episode, Bart is sent to the hospital after eating a bowl of Krusty-O’s that had metal in it. While at the hospital, Lisa sees that her jazz idol, Bleeding Gums Murphy, is also a patient … and sadly isn’t doing well.

After Bleeding Gums dies, Lisa makes the local radio station play his album Sax on the Beach in tribute. As the song plays, Bleeding Gums appears in a cloud (parodying The Lion King) and he and Lisa play a rendition of Carole King’s hit song Jazzman. It was a touching sendoff to Bleeding Gums Murphy, one of the few townspeople in Springfield who nurtured and encouraged Lisa.

8. See My Vest

If you thought Cruella de Vil was a wicked villain, then you’re going to faint when you see the atrocities committed by Mr. Burns in season 6’s Two Dozen and One Greyhounds. In an episode clearly inspired by 101 Dalmatians, Mr. Burns wants to turn a litter of greyhound puppies into a suit.

In his Be Our Guest-inspired musical number, Mr. Burns sings about all the clothes he has made from the fur, feathers, and skins of various animals, including gorillas, albino rhinos, poodles, gophers, and more. He’s a ruthless monster … but, then again, he sure knows how to put on a good show!

7. The Amendment Song

After Bart accidentally gets Itchy & Scratchy taken off the air in season 7’s The Day the Violence Died, the show is briefly replaced with an “edutainment” series that’s clearly spoofing Schoolhouse Rock. The show’s first topic: amendments. Done in the style of I’m Just a Bill, The Amendment Song is all about a poor little amendment who just wants to get passed by congress.

His goal? To make flag burning a crime punishable by a police beating. As the amendment says in the song, “those liberal freaks go too far.” The problem is that free speech is protected by that pesky Constitution everyone’s always talking about, so he, the amendment, needs to get ratified in order to limit free speech. The song is hilarious and, sadly, has become way more relevant now than when the episode premiered in 1996.

6. The Canyonero’s theme song

The Canyonero appears in a few Simpsons episodes and games, and why shouldn’t it? As its theme song says, it’s “65 tons of American pride” and is a “country-fried truck endorsed by a clown.” Also, it’s prone to spontaneous fires and has been deemed unsafe for both city and highway driving.

The Canyonero poked fun at America’s obsession with large gas-guzzling SUVs like Hummers, Jeeps, and Ford Excursions. Luckily, in recent years, as society becomes more aware of climate change and pollution, the super-huge-way-too-big-to-be-on-a-road SUV trend seems to be coming to an end. But fear not, we will always have the Cayonero.

5. Cut Every Corner

In season 8’s Simpsoncalifragilisticexpiala(Annoyed Grunt)cious, the Simpson children get a new nanny, Shary Bobbins. And unlike that uppity blowhard Mary Poppins, Ms. Bobbins has no desire to make the children better. Instead, she teaches them the real lessons of life.

In her song Cut Every Corner, she teaches the kids how easy it is to clean up your room when you cut every corner. Dirty clothes can be hidden under your covers, your toys can be thrown into the closet, and random knickknacks can be tossed in drawers, under the bed, or thrown right out the window!

4. Goodbye Middle Class

In one of The Simpsons‘ most subversive and powerful episodes in years, season 33’s Poorhouse Rock really brought the show back to its roots of calling out America for what it is. The entire second half of the episode plays out like one giant musical, thanks in part to guest star Hugh Jackman ,who leads many of the songs.

The episode calls out America’s dwindling middle class and explains how outsourcing, offshoring, automation, and greed mean that the current generation will never achieve the wealth of their parents because companies no longer pay high wages for menial work. To make it worse, right-wing politicians romanticize the past in order to manipulate older generations into believing that young people are struggling because they’re simply lazy or bad. The episode is traumatically real and relevant, but also masterfully done. It’s proof that The Simpsons still knows how to use its voice.

3. Checkin’ In

In season 9’s The City of New York vs. Homer Simpson, the Simpson family heads to the Big Apple. While there, they check out the new Broadway musical, Kickin’ It: A Musical Journey through the Betty Ford Center. The musical’s big number is Checkin’ In, which is about a Hollywood star who should go to jail for everything he’s done wrong while high on drugs … but since he’s rich and famous, he simply gets sent to the Betty Ford Center.

The phenomenon of celebrities going to rehab became en vogue once again in the 2000s, when everyone from Lindsay Lohan to Britney Spears, Kelly Osborne, and Tara Reid found themselves going to the ultraglam Promises Malibu rehab center. In a 2011 article, ABC News reported that the center’s 31-day rehab program costs anywhere between $55,000 and $90,000. The song ended up earning The Simpsons an Emmy.

2. We Put the Spring in Springfield

The Simpsons received another Emmy for season 8’s Bart After Dark, where Bart finds himself working at an illegal house of burlesque. Once the house of ill fame is discovered, the ladies need a smashing musical number to help remind the people of Springfield that they’re just “that little extra spice that makes existence extra nice!”

The song is catchy, fun, and somehow managed to be all about lascivious thrills without ever coming off as tawdry or offensive. After listening, I think we can all agree that the La Maison Derrière is a Springfield institution that needs to be protected and enjoyed by all.

1. The Monorail Song

Season 4’s Marge vs. the Monorail is universally hailed as one of the best Simpsons episodes ever. It’s an homage to The Music Man and sees a swindling monorail salesman come to Springfield to sell them exactly what a town of 60,000 people with no centralized business district needs — a monorail!

Marge is upset that taxpayer money is going towards uch a frivolous project and says, “Main Street’s still all cracked and broken”, but Bart reminds her, “Sorry, mom, the mob has spoken.” This is The Simpsons at its finest: highbrow in its references, yet still accessible and clever enough to be both funny and sweet. It doesn’t matter that you don’t know what The Music Man is, The Monorail Song stands on its own, and is even better than the source material it’s lampooning. So, let’s all rise to our feet, wave our hands, and sing, “Monorail! Monorail! Monoraaaaaail!”  I’m sure nothing could go wrong …

The first 33 seasons of The Simpsons are available to stream on Disney+.

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