The decline of The Simpsons has been well-documented, but every time we lament the downfall of the show we tend to overlook a certain aspect.
Yes, fewer jokes are landing now and episodes are noticeably weaker as a consequence, but focusing on that alone does a disservice to one of the other elements which made Matt Groening’s creation so wonderful.
We’re talking, of course, about the musical numbers.
This month marks 25 years since the episode ‘Homer’s Barbershop Quartet’ first aired, bringing audiences the dulcet tones of The Be-Sharps and their undisputed banger of a single ‘Baby on Board’.
However, while there’s no faulting that song, plenty of others can lay claim to the title of the best in The Simpsons. Here is our definitive ranking and, by extension, the definitive ranking of every Simpsons song we could bring to mind.
To qualify, it has to have appeared in an episode of the show (during the period when we were still prepared to acknowledge its existence, so no season 20 nonsense here), rather than being a standalone Simpsons-affiliated song, and - as with the episodes themselves - ‘Treehouse of Horror’ segments are not canon.
We will be taking no further questions at this time.
40. Happy Birthday Mr Burns (Season 5, Episode 4: ‘Rosebud’)
As a comic moment, this is great. That’s not what we’re judging it on, though. You can see why Mr Burns wanted the Rolling Stones killed.
39. Luke Be a Jedi (Season 10, Episode 9: ‘Mayored to the Mob’)
The episode ‘Mayored to the Mob’ arrived just around the point where The Simpsons was beginning to lose its way, retaining the funnier moments but giving you the impression they didn’t necessarily ‘fit’ with the show as a whole. If ‘Luke be a Jedi’ was meant to parody this status quo, it could be considered very prescient. Was it, though?
38. Mein Bratwurst (Season 8, Episode 13: ‘Simpsoncalifragilisticexpiala(Annoyed Grunt)cious’)
The delivery from a young Rainier Wolfcastle is flawless, but it is over pretty much as soon as it begins. That’s not always a bad thing, but here it feels as though we’re missing out on endless potential.
37. Everyone Else Loves Ned Flanders (Season 4, Episode 19: ‘The Front’)
36. In The Garden of Eden (Season 7, Episode 4: ‘Bart Sells His Soul’)
A nice gag, but there’s too much competition for this to rank any higher. Still, a nice reminder of when Kirk and Luann van Houten were still happily married.
35. Cletus the Slack-Jawed Yokel (Season 7, Episode 21: ‘22 Short Films About Springfield’)
Okay, this bucks the earlier trend up to a point. It’s limited, yes, but that folk’ll/yokel rhyme is flawless. Some Simpsons songs don’t need to be more than a few words, and knowing when to stop can be just as important as knowing when to carry on.
34. Capital City (Season 2, Episode 5: ‘Dancin’ Homer’)
Okay, let’s get things straight: some songs can be too good for a show like The Simpsons. This predates the golden era of the show which came in between seasons 3 and 8, arriving when the show was finding its feet (albeit with some standout moments) and this is good sonically but not Simpsonically. Does that work? Who knows.
33. Hark to the Tale of Nelson (Season 6, Episode 24: ‘Lemon of Troy’)
You will watch these few seconds and a smile will break out on your face. We don’t make the rules, that’s just how it is. With little room for musical interlude in the extremely well-written ‘Lemon of Troy’, even this much is enough.
32. Springfield Springfield (Season 5, Episode 8: ‘Boy-Scoutz ‘n the Hood’)
You’ve got fond memories of this one, remembering its presence smack bang in the middle of the show’s glory days, and you’re half right. It belongs in a great episode (’Boy-Scoutz ‘n the Hood’, complete with that Ernest Borgnine cameo) but the song itself flatters to deceive on further listens. It’s far from the worst, but neither is it as good as it could have been.
31. Send in the Clowns (Season 4, Episode 22: ‘Krusty Gets Kancelled’)
One day someone will reframe The Simpsons with Krusty as the tragicomic hero at the centre of everything, and it’s no less than he deserves. You know, like those recut trailers which used to be all the rage. He’s the leading man we never knew we had, and a true entertainer.
30. Flaming Moe’s (Season 3, Episode 10: ‘Flaming Moe’s’)
This Cheers parody is a nice touch, within an iconic episode, but some of the higher entries are more than just nice.
29. Homer’s Food Song (Season 11, Episode 3: ‘Guess Who’s Coming to Criticize Dinner?’)
One of the later entries on this list, coming in the season 11 episode ‘Guess Who’s Coming to Criticise Dinner’, this untitled food song retains some of the Homer magic which hadn’t quite gone for good in 1999. It’s TV’s equivalent of Michael Owen’s winner in the Manchester Derby: one of those late, fleeting moments to remind you there was once unmistakeable greatness there.
28. The Mediocre Presidents (Season 4, Episode 15: ‘I Love Lisa’)
Some of the most beautiful moments in The Simpsons are those which have absolutely no bearing on the episode as a whole; whose chief aim was to just allow the writers to have a little fun. It’s the sort of thing that was made possible by the flawless writing throughout the episodes, guaranteeing that any such moment strengthened the material around it rather than feeling out of sync. Back then it was about synchronicity of style, rather than of plot, and this is no better encapsulated than in a short aside involving schoolchildren singing about presidents Taylor, Tyler, Fillmore, Hayes and, of course, William Henry Harrison. In just 20 seconds, we get the tight attention to detail that characterised the show’s best years.
When there are so many great original songs, it takes something really special for a parody to break up the party. This take on Mary Poppins falls into the ‘good-but-not-great’ category, bridging the gap between flawless parody and self-aware takes which spanned entire episodes, both song and non-song.
26. Adults/Kids (Season 10, Episode 11: ‘Wild Barts Can’t Be Broken’)
The key to all great television is conflict, and the Kids v Adults song has it in spades. The Simpsons has always been about the external battle between the younger generation and the smarter-yet-dumber folks many years their senior. It fits with Lisa being the show’s brain and Homer being its outlet for empty thoughts, and is almost a commentary on those who dismissed the possibility of an animated show having gravitas. Of course, as the show’s creators have reached the age of their original critics, the dynamics have arguably shifted.
25. Hank Scorpio Theme (Season 8, Episode 2: ‘You Only Move Twice’)
The most iconic single-episode character has a theme song to boot. It’s a proper spin on a Bond theme from someone who wouldn’t be undeserving of his own moment in the spotlight keeping 007 at bay - you can just picture yourself sticking this on your headphones while relaxing in the hammock district.
24. The Ballad of Jebediah Springfield (Season 7, Episode 16: ‘Lisa the Iconoclast’)
Another underrated end credits inclusion, this song is a perfectly cromulent addition to the list and a great example of the versatility of The Simpsons’ music when it was on top of its fame.
23. Can I Borrow a Feeling? (Season 8, Episode 6: ‘A Milhouse Divided’)
It is often harder to write a deliberately bad song than a deliberately good one, but this perfectly encapsulates the tragicomic persona of Kirk van Houten. This arrived at a point where the show’s creators and writers knew their characters inside out, and it’s a travesty that we will almost certainly never reach that point again.
22. Mr Plow (Season 4, Episode 9: ‘Mr Plow’)
Plenty of The Simpsons’ best music is characterised by smart lyrics, clever wordplay or great depth. This is not one of those moments. Mr Plow might be a musical ‘Jeremy’s Iron’, but it’s all the better for that.
21. Max Power (Season 10, Episode 13: ‘Homer to the Max’)
20. Sideshow Bob sings HMS Pinafore (Season 5, Episode 2: ‘Cape Feare’)
Another one of those moments where, were you to attempt to break the situation down to explain it, you’d have people left scratching their heads. “So, you’re telling me a 10-year-old tricks a clown’s former sidekick into singing every single number from a Gilbert & Sullivan opera to keep from being killed? You okay, mate?” It loses points for the lack of tweaks to the original, but gains some of them back for sheer preposterousness.
19. I’m Checkin’ In (Season 9, Episode 1: ‘The City of New York vs Homer Simpson’)
‘The City of New York vs Homer Simpson’ has become a rather bizarre relic, having disappeared from TV screens almost entirely after 9/11 (there’s a major scene involving the World Trade Center towers), and this may be why ‘I’m Checkin’ In’ has largely been forgotten about. However, it’s a legitimately well-put-together song, which even won a literal Primetime Emmy award in 1998, but feels a bit…too polished. It would probably top the list of ‘Best songs to feature in The Simpsons’ but not one of ‘Best Simpsons songs’, despite being written for the show. It’s an important distinction, and one which absolutely makes sense in my own head if nothing else.
18. Your Wife Don’t Understand You/Bagged Me a Homer/Bunk With Me Tonight (Season 3, Episode 20: ‘Colonel Homer’)
‘Colonel Homer’ arrived early in the third season of The Simpsons, and found that balance between tenderness and humour which would carry the show for the next few years. If anyone asks you to explain what makes Homer so lovable despite his flaws, show them this episode and his refusal to even consider the idea that he might be the object of anyone’s affection other than Marge’s. The songs - two of which were written by guest star Beverly d’Angelo - are among the more poignant in the show’s run.
17. Jazzman (Season 6, Episode 22: ‘Round Springfield’)
The Simpsons dealt with death differently to a lot of other shows of its time, and it covers the whole gamut: to misquote Max Power, there’s the right way (this), the wrong way (killing off Maude Flanders) and the Poochie way (off-screen, on the way back to his home planet). Here, though, Lisa’s rendition of Jazzman with Bleeding Gums Murphy properly tugs at the heartstrings, while showing off Yeardley Smith’s underrated talent of singing in Lisa Simpson’s voice. Take note, other sitcoms which kill off characters just because they can.
16. Happy Birthday Lisa (Season 3, Episode 1: ‘Stark Raving Dad’)
While some songs tell a story, this is a story telling a song. The moments of affection between Bart and Lisa (see also their embrace in ‘Lisa on Ice’ and Bart spending his jagged Krusty-O payout on a Bleeding Gums Murphy record for his sister) are some of the most genuinely moving in the show’s history.
15. Simpson, Homer Simpson (Season 4, Episode 12: ‘Marge vs the Monorail’)
The opening of the iconic ‘Marge vs the Monorail’ episode sets the tone for those 22 minutes of beauty. Can you break the fourth wall when that wall is a tree?
14. We’re Sending Our Love Down the Well (Season 3, Episode 13: ‘Radio Bart’)
A wonderful skewering of Band Aid-style fundraisers, it would have been more than enough to sonically wrest little Timmy O’Toole from the well, if only he existed.
13. Whacking Day Hymn (Season 4, Episode 20: ‘Whacking Day’)
We miss those days when The Simpsons could devote childlike innocence to words about killing snakes. Most of us reminisce about our salad days, but Matt Groening reminisces about his Whacking Days.
12. Who Needs the Kwik-E-Mart (Season 5, Episode 13: ‘Homer and Apu’)
Is there a better lead-in to a song than “Whether igloo, hut, or lean-to, or a geodesic dome, there’s no structure I have been to, which I’d rather call my home”? Of course not. Loses points due to lying to us through song.
11. Union Strike Folk Song (Season 4, Episode 17: ‘Last Exit to Springfield’)
Part of one of the most flawless Simpsons episodes, ‘Last Exit to Springfield’, this is both earnest and original - if you were to come up with a song to characterise Lisa Simpson’s personality, it would be this one.
And now, the top 10, beginning with…
10. The Garbage Man (Season 9, Episode 22: ‘Trash of the Titans’)
It’s a Willy Wonka and the Chocolate Factory parody, yes, but what a parody. Refusing to give U2 a full song of their own but allowing them to play second fiddle to Homer and the sanitation department was a masterstroke.
9. Baby on Board (Season 5, Episode 1: ‘Homer’s Barbershop Quartet’)
The song that inspired this entire list is a thing of genuine quality, and possibly the best barbershop quartet song ever recorded. Of course, while it’s witty at first, it gets less funny every time we hear it.
8. Señor Burns (Season 7, Episode 1: ‘Who Shot Mr Burns (Part Two)’
If you’re going to get a musical guest star on board, you might as well make use of them. Not only did Tito Puente not murder Mr Burns (sorry, spoilers), but he didn’t murder his delivery of this song either. A spiritual predecessor to some of the great Futurama music which would follow a few years later, Señor Burns might be the first ever use of the phrase ‘Slanderous Mambo’, and surely the best bilingual Emmy-nominated song in an animated comedy ever.
7. Canyonero (Season 9, Episode 15: ‘The Last Temptation of Krust’)
Now we’re talking. A sales pitch for a fictional product which is better than 99% of all real examples of such a thing. The Simpsons might have begun its slide by season nine, but musically it was as strong as ever with both this and ‘The Garbage Man’.
6. Talkin’ Softball (Season 3, Episode 17: ‘Homer at the Bat’)
The sepia tone and easy-listening vibe takes us back to a simpler time, when you could sum up an entire Simpsons episode in one song and have it make sense, and when the sight of a cameo could have you instantly pine for the episode in question and dust off quote after quote. Will we ever settle on which of Lord Palmerston and Pitt the Elder was the greater Prime Minister?
5. We Do (Season 6, Episode 12: ‘Homer the Great’)
The Stonecutters episode is a triumph from start to finish, and ‘We Do’ brings a level of absurdity to the already absurd, something which couldn’t exist as naturally in a ‘normal’ episode but conversely also wouldn’t fit into the more recent bizarre-for-the-sake-of-it material.
4. Monorail (Season 4, Episode 12: ‘Marge vs the Monorail’)
The best episode? Yes. The best song? Close, but not quite. We’d be happy for the ring to come off all of our pudding cans if this piece of brilliance was the result.
3. Dr Zaius Medley (Season 7, Episode 19: ‘A Fish Called Selma’)
It’s a travesty that we haven’t seen a full, all-singing, all-dancing big budget West End performance of Stop the Planet of the Apes, I Want to Get Off. The hierarchy of musical doctors goes Doolittle
2. We Put the Spring in Springfield (Season 8, Episode 5: ‘Bart After Dark’)
The episode ‘Bart After Dark’ has given us so much. The clip of Grampa Simpson entering and immediately leaving Maison Derriere, Hans Moleman’s impeccably delivered “Please Hurry”, and this, the best non-parody song in Simpsons history. If ‘We Put the Spring in Springfield’ was in any other show, it would be the best thing about it. However, that’s not accounting for…
1. See My Vest (Season 6, Episode 20: ‘Two Dozen and One Greyhounds’)
Just flawless. Absolute perfection. No song is as gooood as this. Under no circumstances should you @ me.