The 40 Best Songs in The Simpsons History

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The 40 Best Songs in <i>The Simpsons</i> History

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.

40. “Second Grade Blues”
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.

39. “High to be Loathed”
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).

38. “Happy Birthday Lisa”
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.

37. “Food Song”
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.

36. “Capital City”
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.”

35. “Luke, Be a Jedi”
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.

34. “Max Power”
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.

33. “Everybody Hates Ned Flanders”
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!”

32. “Gonna Paint Our Wagon”
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!”

31. “Marge’s Thrift Song”
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…”

30. “Springfield, Springfield”
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.

29. “Kids/Adults”
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.

28. “One,” aka The deadly fog song
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!”

27. “We’re Sending Our Love Down the Well”
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.

26. “Kamp Krusty Theme”
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.

25. “Señor Burns”
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.

24. “The Garbageman”
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.

23. “Can I Borrow a Feeling?”
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.

22. “Underwater Wonderland”
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.

21. “Play it Cool”
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.

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