As if one needs any more reasons to reflect on the massive pop culture contribution of The Simpsons, it’s easy to forget just how many immediately memorable, catchy pieces of music the show has contributed to the cultural lexicon over the course of 28 seasons. At its heart, The Simpsons is an inherently musical show, and one that has dedicated multiple episodes entirely to music, while peppering its episodes with a constant stream of topical and obscure music trivia. In the same vein as say, MST3k, The Simpsons was always a reflection of the quirks and personal musical taste of its creators.
Granted, as in almost any piece written about The Simpsons, we have to make a certain disclaimer: These songs are mostly culled from the show’s so-called Classic Era. No one truly agrees about which seasons that term constitutes, but it’s safe to say that The Simpsons saw some slow but irreversible dips in quality as it forged into double digit seasons. The fact that it’s still on the air at season 28, and was recently renewed for ANOTHER two seasons, is miraculous. And yet, you may be surprised to find that we did include a FEW songs from later seasons that pass muster.
We should also define what we mean when we say “best Simpsons songs.” They need to achieve a certain length—we all love the “Mr. Plow” jingle, but can you really call 12 words a “song”? It’s just not quite long enough. Likewise, this is a list entirely of original songs, not simply real-world songs sung by characters on the show—or else something like Lisa’s rendition of “Jazzman” would be an excellent addition. There are too many great original songs in the history of The Simpsons to dive into the covers.
So here we go. The best songs in The Simpsons history.
Episode: “Moaning Lisa,” season 1
Season 1 Simpsons is a lot like season 1 MST3k, to use that comparison again—neither of the shows are really done cooking yet, and neither of them have found their true identities. It shows in songs like “Second Grade Blues,” which is simply much more sincere than the kind of song the writers would have created a few seasons later. Still, it’s a historic moment in Lisa’s canon—the moment she embraces her passion for the jazz and finds a mentor in Bleeding Gums Murphy. The song itself is a bit cheesy when watching in 2016, but it’s the musical moment from which the rest of them all flow.
Episode: “Gorgeous Grandpa,” season 24
A song from season 24? Well yes, ONE. Don’t expect any more. The songs, like everything in The Simpsons, have become much more forced and perfunctory as the show has dragged on, as even the show’s creators have admitted. But of all the late-era songs, this one is the best, likely because it’s coming from the great Monty Burns. An ode to the joy of villainy in an episode about the joys of playing a pro wrestling heel, the delivery of the song isn’t great, but that’s more than made up for by the clever wordplay and animation—especially when Burns runs through a litany of classic villains in the form of shadow puppets. It’s not at the top of the list, but it’s proof that a good song on The Simpsons is still possible (though unlikely).
Episode: “Stark Raving Dad,” season 3
Season 3 is the start of the unquestioned Simpsons golden age, but this song still hangs on to a little bit of the smarm and sincerity you’d find in seasons 1 and 2. Perhaps that’s because it was written by the perpetually optimistic Michael Jackson himself? Jackson’s involvement in the episode was a complicated thing—he voiced the character of Leon, but did so under a pseudonym because he wasn’t contractually able to sing. Likewise, the actual singing of “Happy Birthday Lisa” was provided by sound-alike Kipp Lennon. Whatever. The song is a pleasant, upbeat, sincere birthday wish from Bart to his sister; the kind of thing you’d never see later in the series when all the characters were more self-aware and cynical. It’s one of the show’s more genuinely kind moments, but isn’t the kind of thing that makes you laugh.
Episode: “Guess Who’s Coming to Criticize Dinner?” season 11
In general, I sort of love the idea of music like the simply titled “Food Song” when they crop up in The Simpsons—not actual “musical numbers,” no supporting instrumentation, no “immersion”—just Homer amateurly singing and looking like a fool. In this case, he’s not even singing for any particular reason; he’s just joyful in expressing his love of various foods, whether they be pizzas, bagels, etc, etc. The way he’s interrupted by the starchy newspaper editor (voiced by Ed Asner, btw) suggests that if he hadn’t been stopped, he would have just kept on singing about food ad nauseum. Season 11 and 12 are truly the last gasp of the series in terms of occasionally providing very good episodes, and this is one of the bits that makes “Guess Who’s Coming to Criticize Dinner?” a worthy entry in the twilight years of the show’s golden age.
Episode: “Dancin’ Homer,” season 2
Tony Bennett was one of the first notable celebrity guest stars to ever appear on The Simpsons, so getting him to sing “Capital City” was a considerable boon for the young show back in season 2. It’s got a bit of that early season sincerity to it, although there is a wry strain of satire to it as well, poking gentle fun both at “city ode” songs from the likes of Frank Sinatra and the allure of an “urban metropolis” to a humble family from a smaller city like Springfield. Like all good Simpsons songs, it has at least one moment of pure, brilliant absurdism: “It’s the kind of place that makes a bum feel like a king; and it makes a king feel like some nutty, cuckoo, super-king.”
Episode: “Mayored to the Mob,” season 10
Most of all the songs on this list come from main or supporting Simpsons cast members, but this one came from the gregarious Mark Hamill, who we really must say was being an excellent sport in performing the likes of “Luke, Be a Jedi.” Ostensibly cast in a production of Guys and Dolls, the sequence cleverly satirizes Hamill’s own real-world Star Wars typecasting by forcing him to perform the musical while dressed as Luke Skywalker, complete with lightsaber. I love that he also stumbles over the lyrics slightly, suggesting that perhaps The Simspons’ version of Hamill knows this gig is so beneath him that he didn’t try very hard to learn his lines when singing “Uh, and do it for Chewie, and the Ewoks, and all the other puppets …”. It’s a nicely subtle moment.
Episode: “Homer to the Max,” season 10
This is simply a nonsense song we see/hear Homer belting out loudly and proudly while goofing off at his desk at the plant. It’s actually the first of two “Goldfinger” parodies on this list, but not nearly as fleshed out as the second. It is, of course, the result of Homer changing his name to “Max Power” in this episode, a move that drastically and immediately benefits his professional and social life. I love what it effectively and simply conveys about Homer—he’s a fool, but a truly lovable, childlike, innocent fool who gets so carried away with his shiny new toy that he can’t help singing about it for the sheer pleasure of it. There’s not even anyone else in the room, so this is a small slice of Homer’s private fantasy reality; a place completely devoid of self-consciousness, which helps make him a beloved character.
Episode: “Dude, Where’s My Ranch?”, season 14
This episode certainly isn’t great, but the song that launches it was good enough to score an Emmy nomination, so at least there’s that. The source of its greatness largely flows from the legendary David Byrne, one of the more oddball Simpsons musical guests, but the segment just works. Byrne, in Springfield to catalog indigenous folk music, overhears Homer singing at Moe’s, the song being “Everybody Hates Ned Flanders”—a catchy jingle that Homer has written about Flanders’ many annoying failings. The main course (and the version of the song I’m considering as being the entrant on this list) is the fully produced version of the song that Homer makes with Byrne, who gets two full verses to himself. The results are unsurprisingly great, especially the bit with Byrne exclaiming “His Leftorium is an emporium of woe!”
Episode: “All Singing, All Dancing,” season 9
The cracks are definitely starting to show in The Simpsons by this point in season 9, when you get not just a clip show but a MUSICAL clip show, but at least we get a few more original songs out of it as well. The setup is great: Homer rents what he believes is a violent spaghetti western in Paint Your Wagon, but the Clint Eastwood/Lee Van Cleef vehicle turns out to be a pedantic, family friendly musical instead. Even the presence of the “always drunk and violent” Lee Marvin can’t turn things toward a more serious bent! His drunken verse seals the deal: “Gonna paint your wagon, gonna paint it fine; gonna use an oil-based paint, because the wood is pine!”
Episode: “Lisa the Tree Hugger,” season 12
Marge is a hilarious character who doesn’t get her due, largely because her quirks (obsession with bland hobbies, such as potatoes) and latent psychoses are hidden behind the more outlandish personalities of the Simpsons family. But man, she can be profoundly weird when left to her own devices. Her little “song about thrift” that she sings to Bart in this episode is one of those wonderfully unhinged moments, revealing Marge’s naivete and lack of understanding of both her own child and of modern culture. Where did she even learn this song, anyway? Is this carried over from her own childhood? Has she been carrying around this pitch pipe for years, waiting for just such an occasion? How long would this song have gone on, if we hadn’t cut away? I desperately want to know what would have happened after “If you spy a quarter in a pie…”
Episode: “Boy Scoutz ‘N The Hood,” season 5
This is one of those songs where the lyrics and melody aren’t necessarily all that clever or side-splitting, but the visuals are the portion doing the heavy lifting. Emboldened (and heavily medicated) by their “all-syrup Squishee,” it features Bart and Milhouse running amok through their great city, taking in the sights … and somehow managing to see a Broadway production of Cats in the process. The way they flit around like wide-eyed, hyperactive insects, or what Barney eventually dubs as “magic pixies,” really sells the sequence.
Episode: “Wild Barts Can’t Be Broken,” season 10
A clever little parody of the song and melody of a similar song from Bye, Bye, Birdy!, “Kids/Adults” is the culmination of the younger vs. older generation struggle that is at the heart of the plot of this episode. With a jazzy, upbeat tune that sounds similar to the likes of “We Put the Spring in Springfield,” it’s a definite toe-tapper with some solid character moments for many of the city’s residents young and old. We get to see Nelson firmly allied with his fellow kids rather than bullying them for once, Lisa indulging in some rebellion and of course, Rod and Todd as the sycophantic adult sell-outs. The highlight: Moe hilariously and grimly subverting expectations by threatening that “we ought to drown you just, like … cats!” It’s a 1v1, back-and-forth song that cleverly evolves mid-performance when the town’s senior citizens join in to create a three-way dance and redefine the conflict.
Episode: “Treehouse of Horror V,” season 6
When you think about it, it’s a little surprising there haven’t been more memorable songs over the years coming from The Simpsons’ annual Treehouse of Horror episodes, but at least we have this one. It’s great because it’s so completely surprising and unpredictable—the number comes utterly out of left field after Bart wakes up screaming at the end of the “Nightmare Cafeteria” segment, only to learn that there’s still plenty to fear: Namely, “that fog that turns people inside out.” Cheap weather-stripping leads to exactly that outcome, and the entire family is hideously turned inside out in one of the series’ grossest moments … only to spring into a Broadway-style song and dance number in parody of A Chorus Line. The simple disparity between the visuals and the song make it hilarious, amplified by the macabre lyrics. “Just one sniff of that fog and you’re inside out! It’s worse than that flesh-eating virus you’ve read about!”
Episode: “Radio Bart,” season 3
If this episode was taking place in 2016, a “We Are the World”-style parody would be a bit on the stale side, but considering that this first aired in 1992, we can give them a pass. It’s classic Simpsons-style satire on society’s tendency toward “best wishes” and “thoughts and prayers” in a time of distress, rather than genuinely trying to help someone—in this case, to actually attempt to physically get Bart out of the bottom of a well. And naturally at the heart of it there’s Krusty, who never passes up on any opportunity to profiteer and pay off his many (easily avoidable) debts. The inclusion of a random celebrity in Sting is a nice touch that gives the song just the right level of smarm—one imagines he felt better about taking the Simpsons gig when they wrote him in as a shirtless, svelte guy who’s also “a good digger!” later in the episode. The social criticism here is more biting than ever in the “sending you our thoughts, as long as it doesn’t cost anything,” era of social media.
Episode: “Kamp Krusty,” season 4
Who builds a summer camp underneath “Mount Avalanche,” on the shores of “Big Snake Lake,” anyway? I love the circumstances of this song, and that the children subjected to the horrors of Kamp Krusty are actually forced to sing it under pain of punishment. I mean sure, it’s bad enough when you’re trapped at a sham of a summer camp with no actual participation from Krusty the Clown, but forcing the kids to participate in this song just ratchets up the pain from mere indifference to active misanthropy. I especially love the line about the “spic ‘n span infirmary, where all our wounds are healed,” which tacitly admits the propensity toward children getting “wounded” at Kamp Krusty in the first place. But at least it’s equipped with a surly nurse ready to blow smoke in your face. Small blessings.
Episode: “Who Shot Mr. Burns? Pt. 2,” season 7
This is just one tight, tight piece of music, and it’s not surprising that it received an Emmy nomination. It’s not the most joke-laden Simpsons song out there, but “Señor Burns” fits perfectly into the “Who Shot Mr. Burns?” character arc, as we begin to check suspects off the list in part two—turns out that although Mr. Tito Puente (one of the more unexpected guest stars in the history of the show) DID swear revenge on Burns, he intended to do so by way of “slanderous mambo.” It really is quite the angry mambo indeed, when you go and examine the lyrics: “It may not surprise you, but all of us despise you! Please die, and fry in hell, you rotten, rich old wretch! Adios viejo!” And all set to a toe-tapping melody.
Episode: “Trash of the Titans,” season 9
“The Garbageman” is one of The Simpsons’ best straight-up parodies of a song with a well-known tune, although if you really look and compare it to “The Candyman” you’ll see that although it certainly evokes the latter, the song actually has an entirely different melody. But regardless of that, “The Garbageman” works perfectly within the frame of the story—Homer makes all kinds of “crazy promises” to win the position of Garbage Commissioner, and the song and reveal of his white-suited garbage fleet—complete with golden epaulets—is the grand payoff. Featuring a pitch-perfect garbage can cameo from Oscar the Grouch, I love that it’s also a grand musical number with measurable consequences and fallout—immediately after it ends, Mayor Quimby is in Homer’s office demanding an accounting for how Homer managed to blow the department’s entire budget. It flies in the face of the “alternate universe” nature of musical numbers by showing their real-world cost factor.
Episode: “A Milhouse Divided,” season 8
Poor Kirk. Sweet racing car bed or no, his situation becomes increasingly destitute throughout the course of The Simpsons, going from a more or less contented family man to a divorced, jobless loser who can’t even muster up delusions of anything better. In the wake of his poorly received divorce from Luann, Milhouse’s father is clearly undergoing some serious mid-life crisis struggles, and is so addled that he somehow comes to the conclusion that he might be able to have a singing career, despite having zero talent for either musical performance or writing. His one song, the title track of his mix tape, is “Can I Borrow a Feeling?”, a sappy and confusingly penned love song for his ex-wife, which makes odd requests such as “Can you lend me a jar of love?” It’s doubtlessly the most pathetic song on this entire list—the fact that Kirk actually believed it would work in winning his wife back just illustrates how deep his problems really are.
Episode: “Homer Badman,” season 6
Homer does a good job of describing his own character in “Homer Badman” when he says that he’s so bashful that he “can’t say titmouse without giggling like a schoolgirl.” The collective impression of Homer Simpson is too often that of an uncouth, loudmouthed neanderthal, but at his core, there’s something more innocent and childlike about him—he’s less Ed Bundy and more Hal Wilkerson from Malcolm in the Middle. When faced with adversity, his natural inclination isn’t to get mean; it’s to escape into a happier fantasy, which is exactly what he does in the “Underwater Wonderland” song when accused of sexual harassment by the family’s babysitter. Rather than face the realities of the situation, he instead fantasizes about the simple pleasures of living “under the sea,” where there will “be no accusations” and he’ll be free to eat whichever unfortunate, random sea creatures get too close to his mouth. The best part of this song, though, is the aftermath, for two reasons. First, Marge’s reaction, which suggests that “moving under the sea” is apparently Homer’s go-to fantasy any time the family is faced with adversity. And second, the fact that when the song ends, we see Homer standing on the couch with his arms raised to the sky, suggesting that he’s apparently been physically acting out the entire sequence for everyone in the room. This is hilarious to me for reasons I can’t even fully articulate, so I’ll say no more.
Episode: “Lady Bouvier’s Lover,” season 5
This is legitimately one of the strangest pseudo-songs in the history of The Simpsons. “Play it Cool” isn’t quite like anything else that’s ever been featured on the show—the blue-tinted, Picasso-esque art style that kicks in as soon as it begins sets an entirely alien frame of mind, almost reminding one of the fantasy world that Homer visits in season 8 after indulging in one too many “Guatemalan insanity peppers.” The lyrics, meanwhile, are simplistic but an obvious play on “cool jazz” or spoken word pieces, right down to the double bass and cymbal brushes. Character-wise, it’s a fun little inversion of “father-son” talks, with Homer offering advice to Grandpa on how he might romance Marge’s mother, which Abe readily absorbs. The hilarious punchline, with Grandpa immediately forgetting all of that advice and reacting with panic to her presence, is just the icing on the cake.
Episode: “Homer at the Bat,” season 3
A brilliant parody within a parody, “Talkin’ Softball” chronicles the Springfield power plant’s fateful softball championship with a tune from Terry Cashman, who is satirizing his own “Talkin’ Baseball.” The importance of “Homer at the Bat” to the series has been expounded on in depth elsewhere, but it was the first time that so many big celebrity voices had been involved in an episode at the same time, and it delivered one of the series’ early classics. The song humorously ticks off the “nine misfortunes” that befall Mr. Burns’ various softball ringers, from “Steve Sax, and his run-in with the law” to “Ken Griffey’s grotesquely swollen jaw,” the result of GIGANTISM caused by too much “brain tonic.” Its callousness toward the MLB players is very funny, especially the line “Mike Scioscia’s tragic illness made us smile.”
Episode: “Gump Roast,” season 13
Honestly, it’s almost unfathomable that a song this great came from a Simpsons season as late as #13, but it’s probably safe to say this is by far the best song on the show after season 10. Following the “Gump Roast” clip show, it starts out by simply listing some of the memorable Simpsons episodes from over the years, from the discovery of Homer’s long-lost brother Herb to the fateful disaster of the Springfield monorail. The really brilliant portion comes next, though, as the writers lampshade the idea that the show had long-since jumped the shark and run out of ideas. The lyrics are absolutely brilliant: “Have no fears, we have stories for years! Like, Marge becomes a robot? Maybe Moe gets a cell phone; has Bart ever owned a bear? How ‘bout a crazy wedding? Where something happens, and doo doo doo doo doo doo. Sorry for the clip show; have no fears, we have stories for years!” In the same manner as they do in season 7’s “138th Episode Spectacular” clip show, the writers satirize the show’s longevity and prove they can still be funny—all the more sad, considering that the show is now more or less the same stale mess they were suggesting it would become. But even now, this song remains a riot.
Episode: “Homer’s Barbershop Quartet,” season 5
It’s nice to balance out the bitingly acerbic songs with a sweetly sincere one now and then, and “Baby on Board” is just that—an unusually heartfelt, genuine song to come along at this period in The Simpsons development, and one that stands out for both its simplicity and catchy nature. The sums up the whole oeuvre of “Homer’s Barbershop Quartet,” which gently parodies the trajectory of The Beatles but mostly exists to dive into the friendship dynamic between Homer and some of Springfield’s key supporting players—Apu, Barney, Wiggum and Skinner. It’s a bit unusual for a Simpsons song in the sense that we hear it multiple times throughout the episode, but unlike the Be Sharps’ punny name, it’s not “less funny every time you hear it.”
Episode: “Simpsoncalifragilisticexpiala(Annoyed Grunt)cious,” season 8
It was extremely difficult to decide how many songs, and which songs, I wanted to use from this highly musical episode. In the name of getting a few more obscure tracks on the list, I had to cut the superb “Boozehound named Barney” and the just okay “Just the Way We Are.” If you’re missing them—tough! “Cut Every Corner” is the signature song of magical nanny Shary Bobbins, an obvious parody of “A Spoonful of Sugar,” but clever as hell regardless. I love how it doesn’t restrain itself only to the bedroom of the Simpsons children and instead spills out into town, as we see how various Springfield residents such as Chief Wiggum and Apu also shirk their duties to get by. And of course, it gets a lot of mileage out of putting filthy language into the mouth of the otherwise sweetly angelic Shary Bobbins.
Episode: “Last Exit to Springfield,” season 4
“Last Exit to Springfield” is one of the very best episodes of The Simpsons, and this song is certainly part of the reason why. Much more sincere than most, it’s an impassioned, fiery, minor key stand of indignation as the employees of the power planet go on strike to regain their lost dental plan. It is, so help me god, actually an inspiring message, and a perfectly crafted parody of American folk songs built around the legends of working class heroes. It’s also a powerful reminder of the talents of Yeardley Smith, the voice of Lisa, who is simply a great singer! Perhaps moreso than any of the other core family members, Lisa can really carry a tune—and apparently play a guitar, a skill that she manifests out of thin air for this opportunity. But thank goodness she does, or we wouldn’t get Lenny’s immediate request afterward: “Now do ‘Classical Gas!’”
Episode: “Whacking Day,” season 4
Only Springfield, beset by so many problems that its very existence on the map is routinely threatened, could dream up a holiday like “Whacking Day” to distract itself from its troubles. And it’s not just a holiday celebrated by a few spontaneous weirdos—the episode goes through pains to show us that the spirit and history of Whacking Day go all the way to the core of Springfield’s identity. Why else would they educate children in the custom, and train an entire choir of castrati to sing this so-called “Whacking Day Hymn”? Its anti-snake platform is hilarious in its over-the-top cruelty, from out of the mouths of babes: “We’ll break their backs, gouge out their eyes, their evil hearts, we’ll pulverize.” Brilliantly set to the tune of “O Tannenbaum,” it’s great, deranged fun.
Episode: “Flaming Moe’s,” season 3
You’ve got to love the balls on The Simpsons, a FOX show that put together an entire musical sequence that was a parody of an NBC sitcom’s iconic opening sequence in Cheers. This song is great both lyrically and visually, with the heavily shaded, “old-time illustration” visual style perfectly paying tribute to its source material. Of course, this being The Simpsons, they also took the themes of that original tune and made them much more macabre, beginning right off the bat with: “When the weight of the world has got you down, and you want to end your life, bills to pay, a dead-end job, and problems with the wife …”. It really hits at the core of Moe’s business plan at his eponymous tavern: It’s not a place filled with great friends and conversation, it’s a place for killing the emptiness inside and distracting yourself from harsh realities.
Episode: “Simpsoncalifragilisticexpiala(Annoyed Grunt)cious,” season 8
I already included “Cut Every Corner” as the mandatory Shary Bobbins song, but “Minimum Wage Nanny” is the true best song from this particular episode. In addition to being another clever Mary Poppins parody, it’s an illuminating ditty wherein the Simpson children lay out their values and principles in what they want in a permanent babysitter—plus a sprinkling of Homer’s pragmatism and casual misogyny. It perfectly illustrates exactly who each member of the family is: Lisa wants a genuine social connection, Bart wants to “get away with moider,” and Homer wants to be troubled as little as he possibly can. And of course, there’s one thing that everyone in the room can agree upon: Grandpa is unfit for the job.
Episode: “The City of New York vs. Homer Simpson,” season 9
“Checkin’ In” might very well be the most purely catchy song in the entire history of The Simpsons, in the sense that I defy you to listen to it and not find yourself singing or humming it a few hours later. Awards shows agreed bigtime, as it took home both an Emmy and an Annie Award in 1997. The family’s trip to New York was a prime excuse to stick a lavish, Broadway-style musical number into the episode, and the writers chose to make it a howlingly funny criticism of celebrity brushes with the law and the slaps on the wrist they receive as a result. The subject matter isn’t the most revolutionary or groundbreaking, but the lyrics are indisputably brilliant: “I should put you away where you can’t kill or maim us, but this is L.A., and you’re rich and famous!” Most Simpsons fans probably would have been perfectly happy to watch the entire rest of “Kickin’ It: A Musical Journey Through the Betty Ford Center.”
Episode: “Homer the Great,” season 6
You have to admit, The Stonecutters really seems like an amazing club to belong to. Beer busts, beer blasts, keggers, stein hoists, A.A. meetings AND beer night? Sign us up! Their signature song, “We Do,” revels in the secret power that the venerable secret organization holds over popular culture and government. Although we never really see that power exercised in the episode, it turns out that the Stonecutters are responsible for, among other things: Holding back electric car research, covering up the existence of aliens, rigging the Academy Awards and stealing the eyesight of “cave fish” for reasons unknown. Per typical Simpsons greatness, it was also nominated for an Emmy. It’s simply a rollicking, catchy number that makes Homer’s new club look like the coolest organization on Earth, even if they are impeding the logical ascendency of the metric system.
Episode: “I Love Lisa,” season 4
“The Mediocre Presidents” is probably the best song that The Simpsons ever did sheerly for the sake of it being a funny joke. It’s not really connected to the story in any important way, only appearing because it happens at the play that Lisa and Ralph are performing in, but they’re not even involved with the song. One can assume that the idea was just too damn good for the writers to pass up, and by god, they were right. An ode dedicated to the “adequate, forgettable, occasionally regrettable, caretaker Presidents of the U.S.A.,” it stars Rod, Todd and a bunch of Springfield Elementary kids we can’t even recognize as the likes of Millard Fillmore and William Henry Harrison. I mean really, when you’re watching a primetime animated show and they’re cracking clever quips about Millard Fillmore, and making those jokes accessible to the masses, then you know you’re in the hands of a brilliant writers’ room.
Episode: “You Only Move Twice,” season 8
Told you there was a second “Goldfinger” parody on the list. This song has the interesting distinction of not actually appearing in the episode, but instead being played over the course of the closing credits—I can’t help but wonder why, but maybe “You Only Move Twice” was already so packed with great jokes that there was simply no more room. It’s obviously much more fleshed out than “Max Power” was, with clever lyrics playing up both Hank Scorpio’s ruthlessness as a supervillain and disarmingly friendly, progressive personality as a boss and office manager. With “generous pensions,” three weeks paid vacation, and a lunchroom full of “hot dogs and burgers and German beer,” who the hell wouldn’t want to work for Scorpio? Being assigned to the germ warfare or weather machine divisions would be a small price to pay for a cold hefeweizen in the cafeteria.
Episode: “The Last Temptation of the Krust,” season 9
There are a lot of great commercial parodies in The Simpsons, and fake products in the vein of the “Juice Loosener,” but none of them has an amazing theme song like the Canyonero sports utility vehicle. This is just the ultimate parody of American advertising, consumerism culture and conspicuous consumption, a vehicle so large and inefficient that it automatically puts everyone else on the road at risk the second you fire it up. The song is sung by the brilliantly cast Hank Williams Jr., with lines of praise like: “She blinds everybody with her super high beams, She’s a squirrel-squashin’, deer-smackin’ drivin’ machine, Canyonero!” But my favorite bit is the fact that they actually managed to stick a legal defense right into the truck’s theme song: “Top of the line in utility sports; Unexplained fires are a matter for the courts!” There are very few Simpsons song lines better than that one.
Episode: “Duffless,” season 4
“It Was a Very Good Beer” isn’t the kind of parody you’d laud for lyrical brilliance. Indeed, it’s kind of on the plain side, but man, it packs a wallop of genuine pathos. Homer’s largely unchecked alcoholism is the kind of topic used on The Simpsons for the sake of humor on a regular basis—there’s even that time Moe calls the Simpson home worried because Homer didn’t stop by for “an eye-opener” in the morning. “Duffless” is the one episode that really tackles the issue in any depth, but it’s still treated largely with kid gloves—this is a comedy, after all. And yet, in “It Was a Very Good Beer,” we do feel a certain sense of the profound. Young Homer was just a dumb kid; a kid with an extremely unconvincing fake I.D. who was supplied with alcohol anyway because no one cared enough to look out for his well being. He did what he thought was socially cool at the time, to fit in rather than feed a substance addiction. One wonders how differently Homer’s life might have turned out if that grizzled clerk had thrown “Brian McGee” out his store instead of serving him. Probably, it would have gone the same. But the other possibility could have had huge ramifications on Homer’s life. The song makes you consider that possibility, ever-so-briefly.
Episode: “Homer and Apu,” season 5
Quick: Name one other animated TV show song with the phrase “geodesic dome” in it. You can’t, because the writing in classic episodes of The Simpsons was on an entirely other level. “Who Needs the Kwik-E-Mart” is an excellent synthesis of both witty lyrics, characterization of Apu, and visual gags … especially the multiple instances of poor Grandpa having the world pulled out from under him. The writers at this point in the show have such a firm grasp on the nature of the characters that they effortlessly write in awesome little touches like Homer flubbing the rhythm of his line without breaking the catchy, singable nature of the tune. And then the end! The way Apu finishes his big, climactic, Broadway-style note and then immediately gets off his chair and walks away without a word. The way the family plops down on the couch, satisfied with how things have wrapped up “much quicker than usual,” breaking the fourth wall of animated reality. It’s all genius.
Episode: “Bart After Dark,” season 8
In our top five, we have several songs that are excellent examples of the “Springfield ensemble number.” The big finale to the burlesque house quandary in “Bart After Dark” is the rousing, jazzy “We Put the Spring in Springfield,” and it doesn’t sound quite like anything else in The Simpsons, thanks to the saloon-style piano and New Orleans brass. It gets everyone involved in the best way possible—Homer and Bart, Reverend Lovejoy, Wiggum, Quimby, Apu, Jimbo and the fellow bullies, even Grandpa and Jasper, and in classic Simpsons fashion it turns an angry mob on its head. All except Marge that is, who misses the song and then humorously lampshades the absurd concept of spontaneous musical numbers when she asks the crowd to sing it again, only to be denied. But that’s all for the best, as it gives us her abortive attempt at a counter song, sadly cut off after “Morals, and ethics, and carnal forbearance …”
Episode: “A Fish Called Selma,” season 7
The title may say “Dr. Zaius,” but allow me to use this space for all the music/lyrics from Troy McClure’s fabulous musical, “Stop the Planet of the Apes, I Want to Get Off!” Everything in the musical is pure magic: The throwback ape costumes, the breakdancing, the forced rhymes, and the parody of Falco’s “Rock Me Amadeus,” which is one of the most brilliant puns in the entire series. As others have also observed, the closing song has what is probably the best single line in the history of Simpsons musical numbers: “I hate every ape I see, from chimpan-A to chimpan-Z! You’ll never make a monkey out of me!” It even closes with a completely contextless “I love you, Dr. Zaius!”, just to send the crowd home on an artificial, unearned high. The quality of these musical numbers are so high that one can almost imagine the writers coming up with the Planet of the Apes musical idea first, and then writing “A Fish Called Selma” just as an excuse to work it in.
Episode: “Marge vs. The Monorail,” season 4
Simpsons fans seem almost religiously compelled to mention that “Marge vs. The Monorail” was written by Conan O’Brien, ignoring the fact that the late night host also wrote several other episodes, but chief writing credit on this song goes to the great Al Jean, who also wrote so many other classic tunes. It is probably the quintessential Springfield ensemble number, taking place at a town hall meeting where a Music Man-style conman waltzes into town and dazzles the crowd with his phony showmanship. It gives everyone their individual moments, from Wiggum to Grandpa, while also reinforcing the truism that the residents of Springfield are simply idiots—even the “smart people” in town are dumb. Marge’s objection that “Main Street’s still all cracked and broken” and Bart’s reply that “Sorry Mom, the mob has spoken,” sums up the general spirit of Springfield better than any other couplet ever has.
Episode: “The Day the Violence Died,” season 7
This is as good as Simpsons political parody gets … or any animated show’s political parody, for that matter. The show went the extra mile to hammer down the Schoolhouse Rock! realism by getting the original singer of “I’m Just a Bill,” Jack Sheldon, to reprise his role as an amendment that wants to allow the police beatings of “flag burners who have too much freedom.” What could possibly be more politically relevant in the horrific year that is 2016, than an amendment singing “‘Cause there’s limits to our liberties, at least I hope and pray that there are, ‘cause those liberal freaks go too far.” They even nailed the old Schoolhouse Rock! minimalist animation style, with its blank white backgrounds and exaggerated features. If a perfect song is a synthesis of great lyrics, visuals and little extra touches, then “The Amendment Song” is undeniably great.
Episode: “Two Dozen and One Greyhounds,” season 6
On one level, I can say “this was a very tough pick,” but on another it doesn’t seem tough at all. “See My Vest” is pure, distilled Simpsons brilliance, through-and-through. From the moment that the jaws of Bart and Lisa drop open and Mr. Burns starts singing and enumerating his massive, cruelty-driven wardrobe, every line is a stroke of genius. Much of the humor is driven by the absurd tonal dichotomy of the catchy, positive-sounding Beauty and the Beast parody tune and the completely opposing nature of macabre pieces of clothing such as a vest made from “real gorilla chest” or slippers made from “albino African endangered rhino.” There’s seemingly no level that would be too far or too cruel for the evil Mr. Burns, who lets us know exactly that when he sings “Like my loafers? Former gophers! It was that, or skin my chauffeurs.” His brand of what Smithers “once describes as “cartoonish supervillainy just goes so well with this type of performance that it seems completely natural. Even Bart, whose greyhound puppies are about to be murdered and processed into a tuxedo, can’t help but acknowledge how damn good the song is.
Jim Vorel is a Paste staff writer and lifelong Simpsons geek. You can follow him on Twitter.