Featured Essay: The Simpsons Sing the Blues; the Worm Ourobouros Devours Its Own Tail

by By Reverend Forrest.:Gummo.:

The Simpsons Christmas Special premiered on December 17th, 1989. 

I was, coincidentally, in 4th grade at the time, and so, by my reckoning, I am the same age as Bart Simpson should be. Unlike the canonical world of Bart’s future, Lisa Simpson never became president, Hilary Clinton hair or not. In fact, Nelson Muntz became president, lost his second nomination to Principal Skinner, and then won a second chance in 2024. And while The Simpsons did correctly assume Donald Trump would be president, in that first season of the show, people weren’t even really sure what The Simpsons was going to be. At the time, The Simpsons was on Thursdays, up against Bill “History’s Greatest Monster” Cosby, and it wasn’t even winning. 

And while the execrable video games (Bart vs. The Space Mutants is legendarily unplayable, let alone unwinnable) were the primary focus of Groening and Co’s merchandise focus, that first year gave us the first bespoke Simpsons album, “The Simpsons Sing The Blues”, which came out almost exactly a year after the Christmas episode. 

The last song, “Sibling Rivalry”, is a surprisingly straightforward middle-of-the-road duet between Bart and Lisa. However, Yeardley Smith exudes the early Lisa Simpson, before she became the show’s annoying stick in the mud: a smart, soulful, and talented little girl, trapped in a family with rather dead end aspirations, despite Homer’s very impressive role at the nuclear power plant. In those early seasons, Lisa had yet to become what she is now: obnoxious. She had her friendship with Bleeding Gums Murphy, appearing on the album, who, had the writers not killed him off way too early, could’ve been a downright delightful mentor for the girl more than he was. 

I bought “The Simpsons Sing The Blues” with my own allowance, $5 a week, so it took me a month to buy, and I chose to buy it on cassette. My only other cassette was Janet Jackson’s “Rhythm Nation”, which was listened to exactly once, and never again. Once in my hands, though, “The Simpsons Sing The Blues” was my most absorbed listening experience, at least until the Nightmare Before Christmas soundtrack rocked my world the next year down. 

“Do the Bartman” was shown after an early episode, with much ballyhoo. An original animation was included, which was not really necessary, since these were days when Disney would cobble together a reel of bouncing Gummi Bear footage to whatever pop song they could afford that week pretty regularly, but a purpose-made animation for “Do the Bartman,” featuring a set-up similar to the Christmas Special’s opening scene, made this new cartoon that I liked seem important. And what makes it special? It was produced by Michael “History’s Greatest Monster” Jackson, who played the mental institution patient that wrote Lisa a birthday song, and had deliberately (performatively) chosen to strike his name from the credits. 

The other hip-hop attempt on the album, “Deep, Deep Trouble,” is arguably catchier, and produced by DJ Jazzy Jeff, who was still being tossed out of the mansion by Uncle Phil on a regular basis. 

My favorite song on the album is Lisa’s “God Bless The Child,” opening with the line “No synthetic sound, please. I want all-live musicians.” I still think of that line, all these many years later. Luckily, we are spared too much Bart, as Nancy Cartwright simply can’t carry a tune in the Bart voice, hence the insistence on rap, but Yeardley Smith can, and does, bring it. I just wish Lisa had stayed the precocious jazz kid, and never spent her time hanging out with Sir Paul “History’s Greatest Monster” McCartney, who never helped anybody’s career out. 

The Simpsons has, like Homer falling down the side of Springfield Gorge, hit every bump along the way down, sometimes funny, sometimes just pathetic. “The Simpsons Sing The Blues” is a relic of that weird 9 years where a poorly drawn cartoon about yellow bugs was the central outlet of American satire, displacing Mad Magazine, absorbing the writing staff of SNL, and turning the post-Murdoch counterculture into a persistent hum of recursive Moe Szyslak memes. Entire empires of animation have risen and fallen in the meantime. We’ve seen John “History’s Greatest Monster” Kricfalusi rise and collapse into being a general creep, Matt Stone and Trey Parker flourished like ten thousand schools of thought under Mao, and Seth MacFarlane goes from being the most plagiaristic showrunner in history to somehow producing the most watchable Star Trek series since Shatner left the scene. Nowadays, the lucky rabbit’s foot of Rupert Murdoch’s evil dynasty, the stone the builder of the New American Century rejected, was plundered and now lies vestigially impotent at the bottom of the dragon’s hoard of Disney, cheaper to continue to produce than to have to replace with fresh advertisers. Springfield U.S.A. at Universal Studios is set to be retired within the next few years, just so much more crumbling edifice left to time. In this day and age where AI is quite likely just shitting out new episodes of the show and nobody would bother to check, Lisa’s plea for real musicians seems poignant. Even now in this era of podcasts, Mike “History’s Greatest Monster” Mitchell of “Doughboys” came and went, a footnote in the Bodleian Library that is Simpsons history.

The Simpsons has seen the death of mainstream television, with itself as the chief assassin, and yet still shambles along behind it, the empty sockets of its’ eyes blank and hollow, although for those of us with memories of how it used to feel to watch Homer and Pals, we remember when it was alive and kickin’. We remember “The Simpsons Sing The Blues”, where it haven’t even done the majority of it’s kickin’ yet, this new show, invited to visit once a week, and pondered the other six days obsessively, watched religiously on VHS tapes ripped right off the broadcast, commercials and all. The Simpsons was not only still alive, but beautiful. Even Conan O’Brien, elder statesman of comedy, the closest thing we have to a Mark Twain living with us today, had yet to even show us what he could do, which he did on The Simpsons. Yet, back then, it wasn’t the aimless and drifting hulked battleship it is today, rusting away at the back of the naval yard. It was freshly launched, it wasn’t even intended to be the Guarantor, it didn’t yet feel entrusted with America’s Satire™

It used to feel like that. It no longer feels like that. “The Simpsons Sing The Blues” might remind you, although a great deal of it is indistinguishable from the SNL house band of the era. In those early days, Lisa Simpson still had something to say, Bart still had something to rebel against, and Homer was still a blinkered and incompetent authoritarian who sniveled before Mr. Burns. Nowadays, Lisa has nothing of importance to say, yet insists on saying it, Bart is so much in the mainstream that he’s actually kind of old fashioned to today’s kids, and Homer has long since eclipsed the other characters to always be the central focus. Even awful old Mr. Burns has been softened out, no longer a physically vulture-like capitalist, now just a doddering, out of touch old relic, just like Bill Cosby, just like Rupert Murdoch, just like The Simpsons, history’s greatest monsters. 

Reverend Forrest.:Gummo.: is the Official Document Retrieval Specialist of the Church of the SubGenius. When he isn’t returning stolen antiquities to their proper museums, he is designing new tarot cards and writing about monsters. adorablepuppies@gmail.com is his email. https://bsky.app/profile/mv17zn17.bsky.social is his sosh meeds.