Musical episodes are a staple of many modern television shows and – having now been on the air for more than three decades – it should come as little surprise that The Simpsons has more than its fair share of them. Not all of them are classics, but some of the songs featured throughout the show’s early seasons are truly fantastic.
With even the most recent of these songs having first aired more than 20 years ago, most fans have likely long forgotten them – even in spite of their catchy melodies and humorous lyrics. A steady stroll through these The Simpsons episodes of old should be more than enough to jog peoples’ memories though.
10 Baby On Board – Homer’s Barbershop Quartet (S05E01)
It’s not uncommon for the series to explore the past through flashback episodes, but Homer’s Barbershop Quartet is perhaps one of the more elaborate examples of this. In the episode, viewers learn that Homer, Apu, Skinner, and Barney were once a famous Barbershop Quartet known as The Bee Sharps. Their first big hit was a song called Baby on Board.
Inspired by a car warning sign, it’s a simple yet catchy number that sounds more like a professional song than one that was produced for an animated TV show. That’s probably because it was both written and partially performed by Disneyland’s The Dapper Dans, although the show’s characters’ voices also feature.
9 Your Wife Don’t Understand You – Colonel Homer (S03E20)
Following an argument with Marge, Homer finds himself at an out of town redneck bar and happens to catch one of Lurleen Lumpkin’s musical performances. He ends up becoming her manager and this, in turn, leads to the singer becoming infatuated and throwing herself at Homer at every opportunity.
Although voiced by neither, the Lurleen character was inspired by Dolly Parton and Loretta Lynn and this is something that’s fairly easy to pick up on. Even her name seems to be a play on the titular character in the former’s hit song “Jolene,” which would be quite fitting given her attempts to steal Marge’s man.
8 Adults/Kids – Wild Barts Can’t Be Broken (S10E11)
It’s not often that fans of the Springfield Isotopes have something to celebrate, so when the team wins the pennant, Homer and a few of the other barflies go on a drunken rampage. They end up vandalizing the school, which leads to the town blaming the kids and eventually imposing a curfew.
With tensions between the two generations high, viewers are treated to a parody of “Kids” from the Broadway musical Bye, Bye, Birdie! Not only does the rendition utilize the original melody, but it also features a wide range of Simpsons cast members too. Rather than make things better, however, the singing ends up angering the town’s senior citizens who successfully vote to bring in a curfew for anybody under the age of 70.
7 Union Strike Folk Song (Parts 1 & 2) – Last Exit To Springfield (S04E17)
Homer may lack a lot of the qualities that typically define a great leader, but one thing that he has in abundance is charisma. It’s perhaps because of this that he’s able to unite the plant workers against Mr. Burns in an attempt to restore the company dental plan. The resulting episode is one of the show’s best, as too is the song that was written for it.
With Burns unwilling to bend, the workers go on strike and it’s here that viewers are treated to Lisa’s hauntingly beautiful protest song. Unlike many of the series’ other musical numbers, both the music and lyrics for “Union Strike Folk Song” were composed by the show’s writers; which just goes to show how much talent was on hand during those first few seasons.
6 Happy Birthday, Lisa – Stark Raving Dad (S03E01)
Bart can be a pretty terrible brother at times, but deep down, he clearly loves his sister. He’d never admit it, of course, but his actions sometimes betray him. That’s exactly what happens in the season three episode Stark Raving Dad, in which he teams up with a man claiming to be Michael Jackson to write a special birthday song for Lisa.
Some may have preferred Bart’s original lyrics (who doesn’t like being told that their teeth are big and green and that they smell like gasoline?), but the heartfelt song is as touching as it is thoughtful and is made all the more enjoyable by the added vocal talents of the King of Pop himself. It did take a few years for Jackson’s involvement to be confirmed though, with the singer originally credited as “John Jay Smith.”
5 The Monorail Song – Marge vs. The Monorail (S04E12)
Mr. Burns had been dumping nuclear waste around Springfield for years with very little consequence, but his actions finally caught up to him in season four. The town fines him $3 million, which might not be much for a billionaire but could make a huge difference to Springfield. Just when it looks like everybody is on board with Marge’s idea to fix Main Street, however, a new face turns up and wows them all through song and dance.
Promising to put Springfield on the map like he did “Brockway, Ogdenville, and North Haverbrook,” Lyle Lanley’s “Monorail Song” captures everyone’s hearts and convinces them to invest the money in a new Monorail system. Things don’t quite go to plan though, and it’s left to Homer to save the day after one of the new Monorail trains goes out of control.
4 We Put The Spring In Springfield – Bart After Dark (S08E05)
After seven full seasons of incompetent parenting, the fact Marge would leave Homer in charge of the kids is a little surprising to say the least. As one might expect, it doesn’t take long for Homer’s poor judgment to get the better of him and this leads to Bart working in a burlesque house. Needless to say, Marge isn’t too happy when she finally finds out.
With a mob of angry Springfielders at her back, Marge confronts the owner of La Maison Derrière and demands that she and her business leave town. Belle has other ideas though and instead breaks out into a song and dance routine that’s unlike any of the others found throughout the series. Through this, viewers also learn that quite a few of Springfield’s residents are among La Maison Derrière’s clientele, which is both funny and a little disturbing as well.
3 Who Needs The Kwik-E-Mart? – Homer And Apu (S05E13)
Before being phased out due to complaints regarding the show’s portrayal of Indians, Apu Nahasapeemapetilon was a fairly prominent character, especially in the early days of the show. There were numerous episodes centered around the Kwik-E-Mart owner, one of which came about halfway through the show’s fifth season.
After years of selling expired food to Homer, karma eventually catches up to Apu and he’s fired by the Kwik-E-Mart’s corporate overlords. In order to make amends for his misdeeds, he decides to work off his karmic debt to Homer, paving the way for the two to form a close bond. In spite of his redemption though, Apu still misses the convenience store lifestyle, and the Emmy-nominated “Who Needs The Kwik-E-Mart?” song is used to explore his inner feelings and sorrow.
2 We Do – Homer The Great (S06E12)
When he overhears Lenny and Karl talking about a Freemason-like secret society named the Stonecutters, Homer wants in. Despite his incessant harassment though, his friends are unwilling to share their secret which leads to Homer following them to one of their meetings. It’s only then that Homer realizes the sheer scale of the organization and just how many of Springfield’s rich and powerful are involved.
As they all sit down to eat, the Stonecutters begin to sing the aptly titled “We Do,” a song that features some of the best lyrics in any of the series’ numerous tracks. Homer later finds himself as the group’s leader following a series of unlikely events, but his stewardship is so wayward that his not-so-loyal subordinates end up forming a new society called the “No Homers Club” to get away from him.
1 See My Vest – Two Dozen And One Greyhounds (S06E20)
Although best associated with sickening schemes and immoral activities, Mr. Burns has been known to break out into song and dance from time to time. One such occasion came in season six when the evil billionaire steals the Simpson family’s newborn Dalmatian puppies.
Ultimately, Burns fails to channel his inner Cruella de Vil and decides not to go through with his plan of turning the pups into a tuxedo, but not before he serenades viewers with what is arguably the series’ best ever song. It’s catchy, well-written, and gives great insight into Mr. Burns’ character. It turns out he really likes the vest!
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