Way back in season three, Bart pranks the town by pretending to be ten-year-old orphan Timmy O’ Toole trapped down a well with no means of escape. How? By using his new microphone that transmits to AM radios of course. Oh, the ‘90s… we’d probably Skype it in nowadays. But with the police force too fat to fit down the well and rescue the boy, and options of hawks and cryogenically freezing him out of the question, the only reasonable response is a charity single.
After Krusty The Clown called his good friend Sting, he enlists a host of Springfield’s biggest names - including Sideshow Mel, Ranier Wolfcastle, and the Capitol City Goofball - to record a special song with minimal proceeds going to Timmy. Of course, later in the episode, Bart finds himself actually stuck down the well and has to be dug out by Sting and the Simpson family.
8. Happy Birthday, Lisa
Another episode from season three, but this time based around Homer and a man with a very familiar voice. After Homer is mistakenly sent to a mental institution (not sure how much of a mistake they made), he meets and befriends a man believing himself to be Michael Jackson, although he turns out to be a bricklayer named Leon Kompowsky. Following a falling out between Bart and Lisa (Bart forgets Lisa’s birthday), Michael/Leon helps him compose a special birthday song for his sister with the aid of a piano and an upturned bin.
The actual, real-life Michael Jackson leaned his voice to the character of Leon but was credited as John Jay Smith, presumably for boring legal reasons. He also wrote the song Happy Birthday, Lisa and co-wrote Do The Bartman, which went to number one in the UK singles charts. Contractual issues dictated that a sound-alike actually performs the song, however.
7. Doctor Zaius
In one of Selma Bouvier’s many marriages over the years, she gets hitched to actor Troy McClure as a cover up for what his sexual desires actually are (we think they involve fish) and to resurrect his floundering career. In another move to kickstart his return to fame he stars in the musical Stop The Planet Of The Apes, I Want To Get Off! in what Homer describes as “legitimate theater”.
But it wouldn’t be a musical without songs and Doctor Zaius is perhaps one of the most famous songs in Simpson's history, sung by one of its greatest comic creations. A parody of Rock Me Amadeus by Falco, this is peak Troy McClure and the line “from chimpan-A to chimpan-Z” still raises a smile from even the sternest Simpsons critic.
6. We Put The Spring In Springfield
Back in the fifth season of the four-fingered yellow beings, Bart is forced to work at a boring looking old house as punishment for breaking one of its gargoyles. Of course, this being a cartoon and not sounding like much of a plot for the next 20 minutes, it turns out to be a burlesque house - much to Bart’s delight. But after an angry mob turns up to knock down La Maison Derriere, Homer starts to sing about the “heart and soul of Springfield” with the house’s employees and patrons, including Mayor Quimby and Reverend Lovejoy’s dad.
We Put The Spring In Springfield actually won an Emmy for Outstanding Music And Lyrics, and the episode itself Bart After Dark brought us the Grandpa swiftly exiting .gif that you simply cannot escape on social media.
5. We Do
After stalking Lenny and Carl to their secret club, Homer is allowed to join The Stonecutters after it is revealed his dad Abe is already a member. And when the underground club isn't drinking from tankards and eating ribs, they’re singing a shanty about all their shadowy deeds including keeping the metric system down, keeping the Martians under wraps, and holding back the electric car. However, with this being Homer, he manages to balls it up by using their sacred document as a bib and covering it in all manner of bodily fluids.
We Do receive a Primetime Emmy Award nomination for Outstanding Music And Lyrics and is undeniably one of the most quoted songs in Simpson's history, from one of the standout episodes of season six.
4. Who Needs The Kwik-E-Mart
Another one from season five, it’s the imaginatively titled episode Homer And Apu. After longtime Kwik-E-Mart worker, Apu Nahasapeemapetilon is fired for selling Homer rancid meat and giving him food poisoning (twice), he goes to live with the Simpson family to get back on his feet. After weeks of chores, Apu decides to visit the sage Head Of The Kwik-E-Mart corporation to try and ask him three questions... but not before singing a song all about not needing the store after all!
Explaining how he’s come to love the Simpson family’s quirks, he leads the family in a choral rendition of Who Needs The Kwik-E-Mart with each member trying to rhyme with him - which is easier for some more than others. Although sadly, it turns out Apu was lying to them through song.
4. Baby On Board
Yet another song from season five (maybe there’s a trend here?), it’s the smash hit from Homer’s short-lived barbershop quartet The Be Sharps. After finding one of the homer’s old albums at a local swap meet, Homer reveals he was part of a nationally famous group with Barney Gumble, Apu, and Principal Skinner who even released an album called Bigger Than Jesus.
Eventually imploding due to the trials and tribulations of being in a successful touring band (thanks in part to Barney’s new relationship with plum and perfume drinking conceptual artist Kako), the band reunite for a special gig on top of Moe’s Tavern, with former member Chief Wiggum looking on... before fetching the tear gas. Oh, and George Harrison pops up too!
2. Monorail
When the town of Springfield suddenly finds themselves with a lot of money to spend, a meeting is called to decide on how it’s best invested. Enter the very shifty-looking Lyle Lanley. Having sold monorails across the US, he persuades the town’s citizens to hand over all their dosh through the power of song - which is a spoof of Ya Got Trouble from the 1962 film The Music Man.
While Miss Hoover and Barney have their reservations about the monorail, Langley brushes them off with a pithy rhyme, leaving just Marge to sit and ponder the safety and necessity of an inner-city transport system. In the end, it’s Lard Lad donuts that really save the day because there’s nothing they can’t do.
1. See My Vest
How could this list exist without bowing to the majesty of Monty Burns’ finest moment? Okay, it’s actually one of his most devious, wanting to turn puppies into clothes, but you can’t deny a catchy song when it’s in front of you. Managing to pay homage to both 101 Dalmations and Beauty & The Beast in one fell swoop, Mr. Burns shows off the delights of his endangered wardrobe.
Starting with his gorilla chest vest, Burns reveals all the rarities he has to wear upon his person including turtle necks, red robin suits, and his gopher loafers (it was either that or skin his chauffeurs). And while he isn’t able to go through with this evil act of puppy slaughter, Mr. Burns’ contribution to the Simpsons’ musical history is second to none. It will probably never be topped.
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