For more than two decades,The Simpsonshas been delighting audiences worldwide, cementing itself as a staple watch for millions and securing its position as an enduring titan of television. Created by Matt Groening in 1987, the show began life as a series of shorts featured onThe Tracey Ullman Show. Here, the idea proved so popular among audiences that it was commissioned by Fox as an independent series in 1989, giving us the animated sitcomas we know it today.
With an impressive 38-year run and a staggering 758 episodes to date,The Simpsonshas not just endured as one of thelongest-running TV showsever made, but also evolved into a cultural phenomenon, gifting us with a plethora of unforgettablemusicalmoments, many of which have themselves become embedded in pop culture, so stick around as we explore and celebrate the top 10 of these iconic musical interludes.

10Anyong PussyCat
Season 19, Episode 7: Husbands and Knives
In “Husbands and Knives,” Bart and Milhouse lock horns with the cantankerous Comic Book Guy, they turn their attention to the new comic book store on the block, Coolsville, owned by the much more agreeable Milo and voiced bythe legendary Jack Black.
What Makes It Great
At the store’s grand opening, Milo surprises everyone by playing a Korean rendition of Tom Jones' classic “What’s New Pussycat,” called “Anyong Pussycat,” then swiftly and enthusiastically joins in, proclaiming Korean covers of Tom Jones songs as a favorite genre of his. Understandably. Black’s famously impressive vocals working in conjunction with Jones' original hit, against the musical backdrop of K-pop, is something that probably shouldn’t work and yet, somehow, it just does.
9Maybe I’m Amazed
Season 7, Episode 4: Lisa the Vegetarian
During a visit to the petting zoo in “Lisa the Vegetarian,” Lisa forms a strong bond with an adorable lamb, prompting her to become a vegetarian, a lifestyle she struggles to maintain due to her friends and family’s lack of support. Fortunately, however, she comes across Paul and Linda McCartney, who inspire her to commit to her decision with the help of “a recipe for a really rippin' lentil soup,” which features on the show in the form of a modified version of McCartney’s “Maybe I’m Amazed.”
As the credits roll, this rendition of the song begins with viewers quickly picking up on the additional noises that seemed to feature, playing it backwards as per McCartney’s instructions within the episode and, sure enough, that really rippin' lentil soup recipe was revealed. A significant moment inThe Simpsons’ long history, “Lisa the Vegetarian” is one of the few episodes to introduce a change that would remain in canon for the rest of the series. The McCartneys agreed tothe guest appearanceson the condition that Lisa would remain vegetarian for the duration of the show, a promise creators have honored to this day.

8The Garbage Man
Season 9, Episode 22: Trash of the Titans
When the town’s garbage men fail to collect the Simpson family’s excessive amount of trash, an enraged Homer decides to run for commissioner in an effort to fight this alleged injustice. Winning on the promise of a new round-the-clock garbage collection and cleaning service, Homer goes on to detail his plans through the preppy little number, “The Garbage Man,” a parody of “The Candy Man,” featuring a fleeting appearance from guest stars, U2.
With the performance taking place solely in Homer’s mind, there are no limitations as to what his service can do, resulting in a town-wide musical number excitedly demonstrating the merits of this system and its creator, with Homer taking on awhimsical Willy Wonka-esquerole in this modern cartoon take on a live action classic.

7Peaches for All
Season 22, Episode 18: The Great Simpsina
When the Simpsons decide to go peach picking in “The Great Simpsina,” they meet peach farmer and enthusiast, Ewell Freestone, who sings them a charming song detailing the various kinds of peaches they may encounter on their expedition.
Whilst both Bart and Lisa make their best efforts to escape the allegedly never ending song, we find it quite delightful as Jack McBrayer, who voices Ewell, delivers an enthused and excitable performance, preaching the word of the peach. With a distinct country twang and a banjo to match, its endless fruit-filled fun for all as we hear of peaches, moldy, grouchy, juicy, god-fearing, and so on.

Season 4, Episode 12: Marge vs. the Monorail
Perhaps one of the show’s most famous musical numbers, “Monorail” is performed in the aptly titled episode “Marge vs. the Monorail,” in which the town holds a meeting to decide what to spend a surplus of money on. Before a decision is made, however, suave salesman Lyle Lanley materializes to pitch his idea of a monorail, the benefits of which he explains through song.
Starring latecomedy legend, Phill Hartmanas the fast-talking Lanley, the monorail song is performed in true musical theater fashion, with the ensemble consisting of Springfield’s townsfolk, who take to the idea more or less immediately before going on to quite literally singing the monorail’s praises. Inspired by the song “Ya Got Trouble” from the 1958 musicalThe Music Man,“Monorail” is a brief but brilliant parody of old-school musicals with an explosive chorus, elaborate choreography, and a lively leading man to match in the form of Mr Lanley.

Related:The Simpsons: The 10 Most Rewatchable Episodes
5Sending Our Love Down the Well
Season 3, Episode 13: Radio Bart
In this episode, Bart is gifted a Superstar Celebrity Microphone, which boasts the ability to transmit anyone’s voice over AM Radio. After losing his transmitter down the local well, Bart uses his microphone to communicate with the town as the fictitious Timmy O’Toole, the little boy who has seemingly fallen down the well. In response to this, Springfield’s finest — and Sting — band together to create the hit charity single “We’re Sending Our Love Down the Well.”
A shameless parody of the 1985 hit charity single, “We Are the World,” Springfield’s well-based equivalent is performed by Krusty the Clown and Sting alongside a choir of Springfield celebs, including Bleeding Gums Murphy, Mayor Quimby and Sideshow Mel among others. Though it comprises only a short part of the episode, the song and its surrounding in-world publicity campaign do an excellent job of parodying the celebrity charity single genre with a host of impassioned solo’s and heartfelt lyrics, such as “There’s a hole in my heart. As deep as a well. For that poor little boy. Who’s stuck halfway to Hell.”
4You’re Going to Like Arts Camp / Arts Education
Season 22, Episode 1: Elementary School Musical
In “Elementary School Musical,” Lisa enrolls in an arts camp, where she meets a host of talented performers, a cow, and Stephen Hawking, all of whom welcome her into the wonderful world of artists with open arms and musical numbers a-plenty.
One such number comes in the form of “You’re Going to Like Arts Camp Lisa,” a parody of the Beach Boys' “Good Vibrations,” performed byGlee’s Lea Michelle, Amber Riley and the late Cory Monteith as Lisa’s fellow camp mates. The original melody, beautiful in its own right in combination with the angelic vocals of the three aforementioned performers, makes for a truly enchanting performance, with lyrical adaptations, such as “I love the elegant pearls you wear. And the starfish shape that constitutes your hair,” adding to the whimsicality. With cartoon creations to match the voices that are oh-so-familiar to a generation of former Gleeks, thisnostalgic TV crossoverof sorts is a treat for fans of the two shows, both past and present.
Related:20 TV Shows That Broke All the Rules
3The Planet of the Apes Musical
Season 7, Episode 19: A Fish Called Selma
In order to quash rumors surrounding his personal life,The Simpsonsin-world star, Troy Mclure begins a relationship with Marge’s sister, Selma, rebooting his career in the process and winning him a leading role in the musical stage adaptation ofThe Planet of the Apes.
Having worked as a copyist onThe Planet of the Apesfilms,The Simpsons’s in-house composer Alf Clausen penned “The Planet of the Apes,” with the result being something quite magical. Like a real musical, the set, costume, and sound come together to create an over-the-top spectacle, which is aggressively theatrical and bursting with ridiculousness, going down in history as one ofThe Simpsons’most iconic musical creations to date. From chimpan-A to chimpanzee, this musical, whilst brief, is both a wild ride and a joy to watch.
2They Have the Plant But We Have the Power
Season 4, Episode 17: Last Exit to Springfield
After Mr Burns attempts to revoke his employees' dental plan at Springfield’s nuclear power plant in exhange for a keg of beer, and with Lisa in need of braces, Homer springs into action as the union president, leading to a strike at the plant which is met with a town-wide power outage. In response to this, Lisa performs “They Have the Plant But We Have the Power” alongside the power station staff, a folk-inspired, beautiful and moving in its own right.
Reprized several times throughout the episode, the song works to unite and inspire the workers with the statement refrain, “So we’ll march day and night by the big cooling tower, they have the plant, but we the power.” Written collectively by Jeff Martin, Jay Kogan, and Wallace Wallordorsky, It’s devilishly catchy and serves and as a prime example ofThe Simpsons’s original music, displaying both humor and lyrical prowess.
1Margarine
Season 19, Episode 11: Episode: That ‘90s Show
When Bart and Lisa discover a box containing Marge’s university degree certificate, confusion arises as the timing of this appears not to line up with Bart’s birth, prompting Marge and Homer to tell their children about a dark and distant part of their relationship, this being the mid- to late-90s. As we flash back to this bygone era, we see Homer reinvent his former band, Sadgasm, in response to an attraction between Marge and her radical feminist revisionist history professor. This leads to the couple’s break-up, at which point Sadgasm releases the hit grunge anthem “Margarine,” a parody of Bush’s “Glycryin” and a song that has absolutely no right to be as great as it is.
“Margarine” is surprisingly well written, with a tune that will pervade the innermost depths of your mind indefinitely. The perfectencapsulation of 90’s grunge, this song about unrequited love is performed by Dan Castellaneta with all the grungy style and unabashed emotion one would expect from the genre.