The Simpsons has been on for over 30 years at this point. In that time, the show has produced some amazing episodes and some real stinkers. But let’s not forget that Fox’s hit animated show about a suburban family trying to make ends meet in Springfield has also provided us with some incredible songs, often mixing laughs with catchy tunes and lyrics.
So we decided to sit down and pick the 15 musical moments from the show’s long history. For this list, we are only looking for original songs, so no Green Day singing the Simpsons theme from the movie, or Homer singing “We Built This City On Rock And Roll!” in the Everglades. This list is also not ranked in any particular order.
With that out of the way, here are our choices for the 15 best musical numbers from The Simpsons. Let us know if we left your personal favorite off the list. We won’t add it later, but we’ll at least look at it and go “Oh, yeah, that was a good one, too!” And that’s worth something, right?
“Monorail Song” – Marge vs The Monorail: S4E12
Let’s get it out of the way: Here’s the Monorail song. It’s great, yes. But it can sometimes feel like the only song Simpsons song people talk about. I love the energy and jokes in this short ditty about conning people into funding a monorail. But I also think the show has produced a lot of other wonderful songs that deserve a spotlight, like the other 14 musical moments making up this list.
“See My Vest”- Two Dozen and One Greyhounds: S6E20
“Like my loafers, former gophers” is just one of many lyrics forever burned into my brain from this cleverly-written season six Mr.Burns song that is not only funny—and it is incredibly funny—but is also an important moment in the episode. It’s here that Burns reveals his plan as Bart and Lisa watch in horror. Okay, well Bart is actually enjoying the song, even if it is about killing his puppies and turning them into a suit. “You gotta admit, it’s catchy.” I agree, Bart.
“We Put The Spring In Springfield”-Bart After Dark: S8E5
Ranking these songs would have been an impossible task. They are all so good! But if you were to ask me my favorite song out of all of these, it would be this jaunty number about a secret brothel in the middle of Springfield that has ties to various important people and moments in the town’s history. Also, shout out to this song providing us our first (and one of only two appearances ever) of Reverend Lovejoy’s father. For you Simpsons lore nerds out there, this is a real treat.
“Cut Every Corner”-Simpsoncalifragilisticexpiala-Doh! cious: S8E13
A parody of “A Spoonful of Sugar” from Mary Poppins could have gone horribly. Plenty of folks have spoofed the classic Disney film and its songs. But the Simpsons version, where the nanny teaches kids how to do jobs half-assed, is so funny and perfectly suited for the show that I wouldn’t be surprised if some folks never realized this was a parody at all. I still love Bart’s lyric “It’s the American way!” Perfect. No notes.
“We Do (The Stonecutter’s Song)”-Homer the Great: S6E12
As a kid, I wasn’t a big fan of this song or episode—where Homer joins an Illumanti-like secret organization—I found it kind of boring and weird. But as I’ve grown up and rewatched the show more times than I’ll ever admit publicly, this episode and this Emmy-nominated song about all the stuff this group controls has become one of my all-time favorites. Apparently, the Stonecutters have been hiding aliens, Atlantis, and more from the public. Most impressively, they made Steve Guttenberg a star. Is there anything they can’t do?
“Talkin’ Softball”-Homer At The Bat: S3E17
When I asked folks for their favorite Simspons songs and musical moments this one didn’t come up much. I think that’s because it’s “hidden” in the credits of the fantastic season three guest-star-filled “Homer At The Bat.” However, when I played folks this parody of “Talkin’ Baseball” they all instantly remembered it or appreciated how wonderful this tune is. It’s overshadowed by an iconic episode, but “Talkin’ Softball” deserves a spot on any list collecting the best Simpsons songs.
“Stop The Planet Of The Apes I Want To Get Off / Dr. Zaius song”-A Fish Called Selma: S7E19
It’s almost cheating to include Troy McClure in a Simpsons song as the Phil Hartman-voiced fan-favorite character—an aging actor desperate for any role—improves practically any scene or episode by simply showing up. And this moment in season seven is no exception. We see McClure performing in a Planet of the Apes Broadway musical and singing some all-time classic lines, including my favorite: “I hate every ape I see! From chimp-pan-A to chimp-pan-Z.”
“Lisa, It’s Your Birthday”-Stark Raving Dad: S3E1
Let’s ignore the weird history around this song—it was performed by a Michael Jackson soundalike but written by the controversial pop star who guested in the episode but under a pseudonym. It’s a mess. Instead, I love this song for how it shows a sweet moment between Bart and Lisa. In the show’s later years, it would forget that the Simpson siblings actually do care for each other. But here, we get to see that. And to this day my wife and I sing this song on our respective birthdays. Oh and ignore the weird extended version that showed up in season 29.
“Canyonero song”-The Last Temptation of Krust: S9E15
In the world of The Simspons, the Canyonero is a massive SUV that takes up most of the road and is extremely unsafe. So of course, Krusty the Clown is the vehicle’s spokesperson. “Top of the line in utility sports, unexplained fires are a matter for the courts!” made me laugh so hard the first time I heard it that I ended up missing the rest of the song. Thankfully, I can re-watch this advertising jingle over and over on YouTube and enjoy it as much as I want in 2024.
“Gonna Paint Your Wagon”-All Singing, All Dancing: S9E11
Clips show episodes suck. Even the creators behind the show admit as much in the DVD commentaries for these network-mandated episodes featuring previously produced clips connected together via a few new scenes. “All Singing, All Dancing” isn’t any different. However, it does include a parody of the real musical western Paint Your Wagon with a song featuring Clint Eastwood and Lee Marvin singing about using the right paint because the wood is “Ponderooooosa pine!”
“Union Song/Classical Gas”-Last Exit To Springfield: S4E17
“They have the plant, but we have the power.” Leave it to Lisa to learn how to play guitar quickly so she can show up and play this funny, but still moving song supporting her father’s union going on strike in what might be one of the show’s best episodes: “Last Exit To Springfield.”
And yes, here’s Lenny asking her to play “Classical Gas”, too. (Man, the Lenny animation as he jams out to her playing is one of the best bits in the entire show.)
“Flaming Moe’s Theme Song”-Flaming Moe’s: S3E10
I always have to double-check that “Flaming Moe’s”—an episode about Homer creating a famous new drink that bartender Moe steals—is a season three episode. It feels like a season six or seven adventure to me. Anyway, this wonderful parody of the Cheers intro feels like something the writers had been wanting to do and this episode finally gave them the chance. Remember folks, “Happiness is just a Flaming Moe away.”
“I’m Checking In!” -The City of New York vs Homer Simpson: S9E1
“I should put you away, where you can’t kill or maim us. But this is LA, and you’re rich and FAMMMOUSSS!” When the Simpsons visit New York, Marge and the kids see a Broadway show about the Betty Ford rehab clinic. And once again the writers are given a minute or so to give us just a tiny glimpse of what this musical is like and based on this funny and catchy tune, I’m ready to buy a ticket and watch the whole thing.
“The Amendment Song”-The Day The Violence Died: S7E18
This parody of the classic Schoolhouse Rock song “I’m Just A Bill” would be a blast even if the producers didn’t get the original voice actor of the Bill to come back and sing in this satirical spin on the famous tune. The lyrics are sharp and witty, with the bill bemoaning all the “liberals” doing terrible things, like burning the flag, and how we need to amend the constitution to add more laws to stop them. But actually getting Jack Sheldon—the original singer—to return adds a level of authenticity to the parody that makes it even funnier.
“Grown Up Halloween”-Halloween of Horror: S27E4
While The Simpsons has long left its golden age, the show is still able to put out a banger tune from time to time. One of my favorites of the modern era comes from what might be one of the show’s best episodes in the 15 years: “Halloween of Horror.” This non-Treehouse of Horror episode provides a well-written and at times tense story about Homer and Lisa being stalked by some shady people on Halloween night. But the highlight of the episode is a parody of “Timewarp” from The Rocky Horror Picture Show about all the adults coming out in their revealing outfits and getting really drunk. If you ever wanted to see the Wiggums doing some BDSM, here you go folks.
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