We Ranked The Best Original Songs From ‘The Simpsons’
Don't make your mind up until you've heard all the songs, okay?!
We’re etching closer and closer to the 30th anniversary of The Simpsons.
That’s right, the show that most likely defined your childhood is marking up a whopping three decades and 23 seasons this year — and recent renewals mean that it’s not going anywhere anytime soon.
The show gets plenty of love for the catchphrases they’ve snuck into the lexicon, and the myriad of meta jokes that went over our head as children — but today’s focus is on the show’s music.
From the second the show bursts to life with its Danny Elfman overture, The Simpsons always tends to have some degree of musicality coursing through its veins. There are several instances where that’s leaned into heavily than other episodes, and today we’re going to be looking at the ten best musical moments to stem from The Simpsons‘ golden era.
Before we get stuck in, some ground rules: Firstly, no instances of musicians turning up to perform their own songs…possibly while high. Cypress Hill, we’re looking at you.
Furthermore, no parodies of existing songs — which, alas, disqualifies the entirety of the beloved ‘Simpsoncalafragilisticexpiali[annoyed grunt]cious.’ We’re honing in on songs written specifically for the show itself, which is a perfectly cromulent way of making a list.
Now, get ready for some well-supervised craziness while you rock out with your father!
#10. ‘Moanin’ Lisa Blues’
Though not quite on the emotional level of their final performance together — a rendition of Carole King’s ‘Jazzman’ that’s probably more famous than the original with millennials — there’s something irrefutably special about the first time that Lisa and her idol, the late Bleeding Gums Murphy, jam together on the bridge during the show’s first season.
The two improvise a bluesy number together, later given the full studio treatment on the album The Simpsons Sing the Blues. It’s our first real insight into Lisa as a developing character, and as such holds its own sense of power to it.
#9. ‘Canyonero’
With lead vocals from country dynasty Hank Williams, Jr., this ad for a new Krusty-endorsed car quickly spirals into pure destruction as its mythology grows larger and larger.
Its train-track drums and whip-cracks recall the theme song for Rawhide, while the talking-blues baritone is pure Johnny Cash (who, coincidentally, has also been on the show).
Full credit to Williams for being so willing to send up his own genre so expertly. If you ignore the en masse deer murder that it’s capable of, as well as its tendency to inexplicably catch on fire, then you’ve got one hell of a car.
#8. ‘Sending Our Love Down the Well’
With the assistance of the Demolition Man himself, Sting, Krusty the Clown put together a charity single for the ages. Think ‘We Are the World’ or ‘Do They Know It’s Christmas?’, but entirely more transparent about how the charity single is more about serving the ego than it is about actually doing anything to help.
Hearing Krusty wailing the vocal ad-libs over the top of the song (“ALLLL THE WAY DOWNNNN”) is one of season three’s flat-out funniest moments.
The one sore point? We never get to hear the song that replaced ‘Down the Well’ at number one on the charts: ‘I Do Believe We’re Naked’ by Funky C Funky Do.
#7. ‘Union Strike Folk Song’
Although not her first instrument (that being the sax), Lisa has been known to bust out the guitar on occasion. She’s pretty good, too — as Lenny found out, she can play ‘Classical Gas’ with little to no preparation. This track, however, is very much in the wheelhouse of your Woody Guthrie or a young Bob Dylan, as Lisa strums about the sorrows faced by her father and his co-workers.
It’s just as rousing as ‘We Shall Not Be Moved’ or ‘This Land is Your Land,’ and it’s one of the more quietly touching moments the show has ever crafted.
#6. ‘Your Wife Don’t Understand You’
Plenty of country stars have made their presence felt on The Simpsons — among them Dolly Parton, Willie Nelson and the aforementioned Cash. Perhaps the show’s most famous flirtation with the genre, however, came with a country star who technically doesn’t even exist. Lurleen Lumpkin, as voiced by Beverley D’Angelo, was a one-off character (at the time, at least) that provided the show with a slew of bar room country tracks for the ‘Colonel Homer’ episode.
None, however, quite land the way ‘Wife’ does — the way it speaks to Homer in the context of the show, not to mention the way it pays homage to the likes of Parton and Tammy Wynette in its execution, makes it a true winner.
#5. ‘Baby On Board’
Well before the show ret-con’d itself up Shit Creek, Homer’s one crowning musical achievement was as a part of Grammy-winning barbershop quartet The Be Sharps.
Co-written and co-performed by real-life barbershop group The Dapper Dans, ‘Baby on Board’ certifiably nails the close, warm harmonies and major-minor tonality associated with the genre.
In the show, it’s penned by Homer, who’s inspired by a new sign Marge has picked out for the back of the car. Although we never hear the original draft in full — “Baby on board/Something, something, Burt Ward” — one can’t help but wonder what might’ve been.
#4. ‘We Put the Spring in Springfield’
Easily one of the show’s more ambitious musical numbers, there’s a whopping 19 characters that get lines in this song, across seven different voice actors. Fittingly, it’s a song that brings the community together, protesting in favour of the burlesque club (the Mason Derriere) upon facing being knocked down.
Everyone from Abe Simpson to Mayor Quimby rallies, and ‘Spring’s brassy take on trad-pop ensures that it stays with you long after Moe’s final trash-can lid smash. The aftermath of the song also provides us with one of Marge’s all-time funniest lines: “Don’t make your mind up until you’ve heard both songs.”
#3. ‘The Monorail Song’
Right up to his untimely passing, Phil Hartman was one of the show’s greatest assets. You may remember him from such classic characters as Troy McClure and Lionel Hutz, as well as one-offs like jive-talking con artist Lyle Lanley.
One of the show’s most overt tributes to musical theatre, Lanley leads this patter song deflecting concerns surrounding the monorail — so convincingly, it leads a full procession out of the Springfield town hall.
Using the township as a hive-mind has always worked as a comedic device (“Don’t push your luck! Don’t push your luck!”), but perhaps never before or since ‘The Monorail Song’ has it created something so uniquely memorable.
#2. ‘We Do (The Stonecutter’s Song)’
To think that ‘We Do’ originally wasn’t included in ‘Homer the Great.’ Could you imagine that episode without it? It got them nominated for a goddamn Emmy, people!
It’s easy to see why, too — the swelling orchestration, as arranged by Alf Clausen, matched with the hilarious lyrics of John Swartzwelder, makes for the song one of the most rousing and anthemic numbers ever penned for the show.
It’s also just short enough to be able to memorise it and sing it out en-masse — with or without Steve Gutenburg.
#1. ‘Oh! Streetcar’
How many of us grew up thinking that A Streetcar Named Desire was a musical thanks to this episode? For many, the classic play was first introduced to us via this ambitious effort from Llewellyn Sinclair, played by Jon Lovitz, who camps up the play’s drama and picks a few majorly inopportune moments for the cast to break into song.
Every snippet from the musical is a winner, from the vamping ‘New Orleans’ to Apu’s solo number ‘Simple Paper Boy.’ Oh, and taking two of the most famous lines from the play and turning them into pure camp musical theatre.
David James Young is a writer, podcaster and one of the chair moisteners over at Sector 7G. When he’s not making music lists, he’s listening to The Simpsons Index. You can find out more about him at davidjamesyoung.com, or just by watching a lot of The Simpsons.