One of TV’s longest running institutions hits another milestone Sunday night, as The Simpsons launches its 38th(!) season. Like many folks, I haven’t kept up with the show for a long time. Instead, I’ve been content to obsessively rewatch episodes from the show’s so-called “Golden Age,” which is generally agreed to have begun with season three and ended around season nine, give or take a season on either side. I’m not sure if being so far behind on current seasons makes me a casual fan at this point, but I keep telling myself I’ll catch up one of these decades ... if they ever slow down a bit!
In any case, a milestone like this gives me an opportunity to look back at my favorite moments from The Simpsons. In particular, my favorite music moments. Here are five of my favorite Simpsons music episodes, more or less in order of how much I enjoy them. I’m well aware there are dozens I’m forgetting (or intentionally excluding). If you feel there are any I've overlooked, please send them my way, I can always be convinced to expand past five!
“Homer’s Barbershop Quartet” (Season 5, Episode 1)
Season Five of The Simpsons begins with the revelation that several years prior, Homer was a member of a world-famous, award-winning barbershop quartet. Through a series of flashbacks, he tells Bart and Lisa the story of his time with The Be Sharps (along with Apu, Principal Skinner, and Chief Wiggum, later replaced by Barney). If this were any other sitcom, the entire preceding sentence would be the premise for the whole show, but because this is The Simpsons, it’s never mentioned again other than the occasional “blink and you’ll miss it” reference.
The whole story of The Be Sharps is based on the careers and lives of The Beatles, with numerous references to Beatles lore and trivia: The Be Sharps called their second album Bigger Than Jesus, and Barney gets avant-garde with it, saying he’s “taking barbershop to strange new places.” It’s all even funnier considering that The Beatles exist in the Simpsons universe. George Harrison even appears in two scenes in this episode, including the final scene, when The Be Sharps perform on the roof of Moe’s (of course). As George scoffed, “It’s been done.”
“Homerpalooza” (Season 7, Episode 24)
As a card-carrying member of Gen X who basically grew up watching The Simpsons, this episode has layers to it, and a little something extra for people my age. In this one, Homer pulls Bart and Lisa out of school and takes them to the Hullabalooza music festival in a desperate attempt to prove to them (and himself) that he’s still cool. (He ends up being recruited to be part of the festival’s traveling freak show by repeatedly getting shot with a cannon, but that’s the least important part of the episode.)
This is the episode that contains one of Grandpa Simpson’s most famous lines: “I used to be with ‘it’, but then they changed what ‘it’ was. Now what I’m with isn’t ‘it’ anymore and what’s ‘it’ seems weird and scary to me. It’ll happen to you!”
On top of that, there’s a lot of extremely specific digs on Gen X in this episode that I didn’t fully appreciate until I got older. The most famous example is the guy who doesn’t even know if he’s being sarcastic anymore when cannonball Homer takes the stage. And finally, this episode has one of the show’s best-aged jokes (Cypress Hill did play with the London Symphony Orchestra in 2024) and also one of its worst (the record store clerk who has never heard of Apple computers).
“The Otto Show” (Season 3, Episode 22)
One of the hallmarks of The Simpsons is that it often doesn’t get to that week’s “A-plot” right away. A prime example of this is “The Otto Show,” which is mainly about the revelation that Otto the school bus driver doesn’t have a driver’s licence. First, though, the episode spends nearly nine minutes on Spinal Tap’s visit to Springfield, with Michael McKean and Christopher Guest making guest appearances (Harry Shearer, of course, was already on board).
After an interview with KBBL (a segment that hits close to home for those of us who interview musicians as part of our jobs), Spinal Tap plays a 20-minute concert that’s riddled with technical errors and ends in a riot. A couple of days later, Otto plays “Freebird” on Bart’s guitar, which causes everyone to be late to school, and then he causes multiple accidents (including running Spinal Tap off of the road and apparently killing them). It all culminates in Otto getting fired from the school district. It all (kind of) makes sense if you watch it.
“‘Round Springfield” (Season 6, Episode 22)
Lisa tends to be the focus of some of the sadder episodes of The Simpsons, and that’s the case here, as she deals with the death of her musical hero and mentor, jazz musician Bleeding Gums Murphy. Although it’s not Murphy’s first appearance, we get a little more of his backstory here. He did record one album, but blew all of his royalties on his $1,500-per-day Fabergé egg habit, then had some awkward TV appearances that did nothing to boost his career. Like so many talented musicians, he wasn’t properly appreciated when he was alive.
Lisa sets out to change this, and buys a copy of Murphy’s record for $500 (she gets the money from Bart, who received a settlement after eating a jagged metal Krusty O from a box of cereal — again, it all makes sense if you watch it). She lends the record to the local jazz station, which is struck by lightning, greatly improving the reach of its signal. All of Springfield is able to hear Bleeding Gums Murphy’s record, and in death, he finally earns the respect he chased while he was alive.
This episode also reveals that Homer has a Starland Vocal Band tattoo that he apparently forgot about.
“Marge vs. The Monorail” (Season 4, Episode 12)
I’ll admit it: I really just wanted an excuse to include “Marge vs. The Monorail,” arguably one of The Simpsons’ best episodes. Naturally, this episode earns its spot on this list thanks to “The Monorail Song,” led by Lyle Lanley (the late, great Phil Hartman) and inspired by songs from Meredith Wilson’s The Music Man, so there’s your Iowa connection (there’s always an Iowa connection).
Years later, it’s interesting to take a look back at this one, because it was a pretty controversial episode among the show’s writers: they felt the surreal tone of the episode was out of step with what The Simpsons had been to that point.
As with music, The Simpsons has unquestionably changed over the years, with plenty of folks declaring that “the good old days” are over. But both music, and The Simpsons, are still around and weighing in on the culture and life around us.
