The recent passing of Simpsons composer Alf Clausen got me wanting to cover an episode in which music plays a significant part. The most obvious candidate was already taken - and besides, I did ideally want it to be an episode in which music is celebrated as something expressive and transcendental, not one in which we simply have a good giggle about how camp and silly musical storytelling is. So "Round Springfield" (2F32) of Season 6 seemed like the best possible option, with bonus points for the fact that it is a story about bidding farewell to a musical legend who maybe didn't get the full recognition he deserved within his lifetime. Debuting on April 30th 1995, this was a historic episode, marking the first occasion on which one of the show's established characters was killed off. It was not the first episode to deal with the subject of death and bereavement - "Old Money" of Season 2 can claim that honor, although the theme of grief was far less pivotal in that episode, with the narrative focus being primarily on Abe's estrangement from Homer. Here, the issue is all the more stark and hard-hitting for being presented from the perspective of one of the show's younger and more ingenuous characters. Lisa left contemplating matters of life, death and resilience when a chance reunion with her mentor, the enigmatic blues musician Bleeding Gums Murphy (guest voice of Ron Taylor), is cut tragically short by an unspecified terminal illness she did not see coming.
I confess that I know very little about how "Round Springfield" was marketed in the run-up to its airing. I personally did not get to see the episode until roughly a year after its Sky 1 premiere, and with the internet still being this weird and slightly alien-sounding rumble on the horizon, I had no means of accessing spoilers online. Later instances in which the show pulled this same macabre move tended to be preceded by promotional blitzs designed to drum up suspense about the identity of the condemned character (Maude Flanders and Rabbi Krustofsky spring to mind, although neither example worked out anywhere near as well as the King of The Hill "Propane Boom" cliffhanger). I would hazard a guess that this did NOT happen here, if only because the "Who Shot Mr Burns?" two-parter was right around the corner, and why would they risk stealing that publicity stunt's thunder? I do not know if viewers were made aware in advance that a character was going to die, let alone if there was any mystery regarding who it might be. Perhaps the title offered a clue to those hip to the 1986 picture Round Midnight, which follows the final days of a drug-addicted saxophonist (played by jazz legend Dexter Gordan) and his friendship with the fan he encounters after travelling to Paris. All I can say is that, having entered into the episode blind, I can attest that it really is the best way to first experience it, with your perspective actually aligned with Lisa's. There are clues, certainly, that something more troublesome might be unfolding (not least in that Lisa finds Bleeding laid out in a hospital bed) but we are at first inclined to share in her naivety, being too caught up in the joyfulness of the reunion, and the robustness of the characters' rapport. Alarm bells might start to ring should we pick up on the fact that the one thing the characters are emphatically not discussing is the nature of Bleeding's condition, as if it's something that neither party can bring themselves to acknowledge. But Bleeding certainly never presents as a man who is at death's door (to the point that it requires some suspension of disbelief that he'd still be able to belt out such a vigorous jamming session on his saxophone in what transpires to be his last meeting with Lisa). He seems much too alive, still so full of passion for his craft and with warmth and wisdom for Lisa. So when tragedy strikes, it comes with a devastating abruptness that feels all-too real. The line between this world and the next is such a fragile one, something this episode captures so bitterly. One moment he's giving Lisa some pointers and encouragement before she plays in her school recital, the next she's rushing back to tell him how well her performance went, only to discover that he's no longer there.
What fascinates me about "Round Springfield" is that it's an episode that allows itself time to be sad, in a way that was honestly quite unusual for this point in the series. There's comic levity in the subplot, which involves Bart suffering at the hands of yet another shoddy Krusty product (a jagged metal hoop that's inexplicably included as a freebie in his brand of cereal), and in whatever Homer is up to on the sidelines (of note, there's a running gag where a hot dog vendor seems to seek him out in the most inappropriate of places), but the loss of Bleeding and its impact on Lisa are treated with genuine reverence. There are points where it honestly seems reminiscent of the more melancholic tone endemic to the first three seasons of the show; it has a certain moodiness of atmosphere, and an eye for emphasising the loneliness and finer disappointments of the characters' lives in a way that was so central to early installments like "Life on The Fast Lane", "Colonel Homer" and Bleeding Gums' debut episode "Moaning Lisa". I tend to think of this model of Simpsons storytelling as having bowed out with "A Streetcar Named Marge" at the start of Season 4, but with the reappearance of Mr Murphy it momentarily lives again. And this would be the big twist - I'm forever blaming this shift in tone on then-showrunners Al Jean and Mike Reiss and their preference for sillier, rapid-fire humor over character-driven storytelling, yet they were actually the minds behind this episode. The script itself was written by Joshua Sternin and Jennifer Ventimilia, but the plot was Jean and Reiss's brainchild, and they receive a story credit. Credits for story alone were unusual on The Simpsons, and it's explained on the DVD commentary that Jean and Reiss requested it on this are occasion because they'd envisioned the episode being a big winner on the awards front and wanted their names attached. (It was all in vain; the Primetime Emmy for Outstanding Animated Program that year was scooped up by another Lisa-orientated episode, "Lisa's Wedding", which offered something even more novel than the death of a jazz musician - a hair-raising peek into the distant dystopian future of 2010). By Jean and Reiss's standards, "Round Springfield" is a remarkably grounded narrative. Even the lighter touches, such as the hot dog vendor, seem deliberately smaller and more restrained than much of what we'd seen them do throughout Season 4. That is, until we get the ending. With the closing sequence, the episode is suddenly immersed in the signature off-the-wall humor that was all over Jean and Reiss's own series The Critic (a perception bolstered in how it is essentially an extended parody of a popular moment from a contemporary movie). That ending is the key element that disqualifies it from playing like a total throwback to those earlier seasons. It is such a deeply bizarre way to conclude this story. I don't even mean that as a criticism. It's weird in ways that are grand, fun and very moving. But if you stop to think about it, what is even going on in that ending? Because surely Bleeding didn't really...well, we'll get to it.
"Round Springfield" is, admittedly, another example of an episode where the optics maybe aren't so great when viewed from a particular angle. I mean, think about this for a moment. They made the bold decision to kill off a (semi) recurring cast member, and they chose one of their few African American characters. In other words, the black guy died first. That had never been done before, right? Adding fuel to the fire is that, when Bleeding Gums Murphy was introduced in "Moaning Lisa", he was a textbook example of the Magical Negro, being a somewhat mysterious black character whose sole function within the story was to make Lisa feel more confident about her place in the world. Now, to an extent, all supporting characters are bound by the law of Simpsons-centrism - the Simpsons ARE the centre of this confounding little universe, and everything the rest of Springfield gets up to must in some way relate back to them and be in service of them. But it's felt particularly strongly with the Elliotts, a group of characters who effectively serve as the family's guardian angels. I went over my reasoning in more detail in my review of "Moaning Lisa", but to recap, "Elliotts" was a term I came up for a foursome of characters from the show's early years (named for the cartoon dragon from Disney's Pete's Dragon), whom I'd clumped into a collective as a sort of counterpoint to the Home-Wreckers - in addition to Bleeding Gums, the others are Karl (from "Simpson and Delilah"), Bergstrom (from "Lisa's Substitute") and Kompowsky (from "Stark Raving Dad"). What they have in common is an uncannily benevolent, otherworldly aura and that they are, significantly, all outsiders to the Simpsons' White Anglo-Saxon Protestant heteronormative domesticity. Bleeding's a Magical Negro, Karl's a Magical Queer, Bergstrom's a Magical Jew, Kompowsky's a...hmm, is the Magical Psychiatric Patient a thing? It could be. The point is that each of the Elliotts represents a marginalised figure within the Springfield community. Their outsider status might have given them a strength and a perspective on life that would otherwise be unknown to the Simpsons, but all that matters is that they're able to share those pearls of wisdom with one or more of the family and go merrily on their way, satisfied that their work is done. They can help to prop up the central dynamic, but they have no business in sticking around to be a part of it. Of the four, Bergstrom is the only one who could be feasibly described as having anything even resembling an agenda of his own (in that he doesn't lose sight of the fact that his time with Lisa is only a short-term job assignment and he'll soon have bigger fish to fry in the projects of Capital City). For clarity, I like the Elliotts and think they're all great and beautifully realised characters, but there's little downplaying that this dubious convention informs a huge part who they are and how the narrative regards them.
Bleeding Gums retains the honor of being the only Elliott to ever be brought back to any significant capacity, even three decades on from the episode's debut, although this wasn't for a lack of interest on the writers' part. (Returns for Karl and Kompowsky were on the cards but fell through. I am not, though, aware of there being any serious motions for a Bergstrom sequel; I suspect that Dustin Hoffman - sorry, Sam Etic - regarded it as a one-and-done gig.) His reappearance in "Round Springfield" might have been an opportunity to expand on his character and have him grow a little outside of his role as a mentor figure to Lisa - but nope, if anything they only doubled down on his Magical Negro credentials, sacrificing him so that Lisa could undergo character growth of her own, before finally depicting him as a literal spirit in the sky, jamming with his newly-enlightened protege to a Carole King tune (like I say, we'll get to that goofy ending in due course).
None of this was done maliciously, of course. But what is just as telling is how Bleeding Gums was singled out as the kind of perfectly expendable character who could be jettisoned for the feels (and the awards bait). The Season 7 clip show "The Simpsons' 138th Episode Spectacular", would infamously mock him (alongside Dr Marvin Monroe) for never having been a popular character, and therefore not one that viewers were presumably expected to care about, although the truth with Bleeding really lands somewhere closer to the middle. On the DVD commentary, Jean does indeed state that they obviously weren't going to kill off a character like Mr Burns whom they'd be wanting to use again, but he also recounts that Bleeding was chosen because he was a character whom people felt warmly toward, in no small way thanks to Taylor's performance. He offered the best of both worlds, in not being integral enough to the core universe that it would be an especially startling development to retire him to the jazz club in the sky, but being sympathetic enough that it would still hurt viewers to see him go. If Reiss had had his way, then the show would have taken a very different path and killed off Marge's mother (a move that Julie Kavner might actually have been fully on board with, as I understand she hated doing Jackie Bouvier's voice), but he concedes that Bleeding turned out to be a better choice. Perhaps bumping off someone within the family, however seldom seen, was deemed too radical. Or maybe it came down to the fact that Bleeding is a fundamentally gentle soul, which Jackie is not. He expresses no outward bitterness or regret for the life that he's led (other than his $1,500 a day Faberge egg habit, which is the closest we get to a heroin allusion), and his legacy is complicated only in the sense that his inherent goodness went under most people's radars. He's a wholly angelic being we're intended to shed a tear for but also conversely write off as a character of no genuine consequence. Outside of what he meant to Lisa, that is.
The Lisa factor is another big reason, I'm sure, why Bleeding was ultimately the one placed on the chopping block. She is such a compelling character around which to craft emotional stories, possessing a wisdom well beyond her years but still having all the vulnerabilities of a child. The loss of a friend like Bleeding would hit her tremendously, even with life already having dealt her so many blows with its cruel impermanences. As Kompowsky's episode made clear, she was very deeply affected by the death of the original Snowball (and her hamster named Snuffy, though he comes up less often). There are also those losses she'd suffered that didn't entail mortality, with her being all but forced to surrender her beloved pony Princess and the man she'd looked up to as a substitute father figure abandoning her for a job in Capital City. In both instances, Lisa's distinctly child-like naivety regarding the impending heartbreak was such a powerful factor. She was so thrilled to have Princess that it seemingly never occurred to her just how difficult and impractical it was for her family to afford such a high maintenance animal. She was so besotted with Bergstrom that she lost sight of the fact that he was never going to be there on a long-term basis. Here, she's so overjoyed to have Bleeding back in her life that she doesn't question what he might be doing in the Springfield Hospital, and it seems that Bleeding doesn't have the heart to outright tell her. Was he himself aware that he wasn't going to make it? Yes, and I think there is a specific moment in the episode where we can pinpoint him making what seems like a conscious farewell to Lisa. It's a scene that hits so hard on repeat viewings, when we know what's coming. As Lisa prepares to go off to her recital, Bleeding hands her his saxophone and tells her to take it with her for luck. While Lisa is honored, she does not grasp the full significance of this gesture, presumably thinking that he's just lending it to her for the recital. With hindsight, it seems obvious that Bleeding gave it to her because he knew he wouldn't be needing it. In addition, by giving her his saxophone he is in effect passing the torch to her to go out and perform great music in his stead. There's a more macabre foreshadowing in his telling Lisa that she's going to "knock 'em dead" (by which he likely to alludes to Lisa's potential to go far in life, not just at this particular recital), followed by an ominous cough, the only symptom of ill-health he's seen to exhibit. Finally, as she leaves his side, there's a lingering emphasis on him waving to her, as if he knows this will be their last goodbye.
What always made the relationship between Lisa and Bleeding so affecting is in how they were ostensibly so mismatched, yet connected so readily as social misfits with a mutual appreciation for jazz and the importance of creative expression. When Lisa first encountered Bleeding back in Season 1, he gave her the much-needed assurance that she was not alone in the world, at a time when she felt that no one understood her. (Perhaps fearing that newer viewers wouldn't know who Bleeding was, the episode incorporates a small clip from "Moaning Lisa", leading to a jarring clash of art styles; I suppose it's not so strange when we consider that for several years the series still felt the need to keep reminding us who Sideshow Bob was every time he showed up.) In "Round Springfield" we see how Lisa is eventually able to return the favour, in demonstrating to Bleeding that his life and music had value, at a time when he seemed destined to die alone and all forgotten. ("You've had some career...although the moral seems to be that a lifetime of jazz leads you sad and lonely." "Well, before you came to visit I would have agreed with you.") Before Lisa, nobody had come to visit Bleeding at the hospital; when she asks about his family, he tells her he doesn't really have one. (In what can only be a deliberate callback to a joke in "Oh Brother, Where Art Thou?", it's heavily hinted that Bleeding and Dr Hibbert are brothers who lost contact a long time ago, although neither party seems to connect the dots. This also means that Bleeding had a second brother he possibly didn't even know about.) The grim reality doesn't fully set in until after his death, when Lisa attends his funeral and discovers that she's the only mourner there; nobody else in town knew who Bleeding was or cares that he's gone. It's a realisation that transforms Lisa's grief into red-hot grit and takes her on her first step toward healing, with the knowledge that responsibility for keeping her friend's memory alive rests solely on her.
Before then, we get a series of short scenes that feel reminiscent of "Moaning Lisa", with the family all showing awareness of Lisa's suffering and doing their bit to try and help, even if they don't necessarily have the kinds of answers she's seeking. Homer looks as though he might have a sensible response, in reminding Lisa of how she coped when Snowball died, but ends up reaching the most inappropriate possible conclusion from that train of thought: "All we have to do is go down to the pound and get a new jazzman." Maggie attempts to soothe Lisa's aching soul the only way she knows how, by offering Lisa her pacifier (it doesn't help Lisa, but the tactic later proves effective on Homer, who is rattled by his own failure to say the right thing). Bart shares with her his belief in reincarnation - specifically, that when you die you can come back in a form of your own choosing. He's intent on being a butterfly in his next life, because as he sees it he'll be able to commit acts of arson and be totally above suspicion. (Something I find particularly disturbing about Bart's butterfly fantasy is the fact that everyone else in it - Skinner, Wiggum, Lou and Eddie - are all the same age they are in the present, so is Bart banking on dying imminently?). Deciding that she needs to consult someone with a little more experience and wisdom, Lisa turns to Abe, who seems to think he's in a Final Destination scenario, with Death conspiring against him at every turning. (Really, the guises in which he sees Death manifesting aren't that far off. Maggie? Well, she'd make an attempt on Burns' life soon enough. Snowball II? As Homer alluded to above, she's a walking reminder of the grisly fate that befell the original Snowball. The bird bath? Odd are that something drowned in there at some time or other.) Marge, who nearly sent Lisa down a terribly destructive path in "Moaning Lisa", here gets to be the voice of reason, assuring her daughter that the sadness she feels is normal and making the practical suggestion that she might honor Bleeding's memory by asking the local jazz station to do a tribute to him. Lisa immediately runs into a roadblock - K-Jazz is happy to fulfil her request, but they don't have Bleeding's sole album, Sax on The Beach, in their library, and copies are hard to come by. As luck would have it, Comic Book Guy has one for sale in his store, but it comes with a hefty $250 price tag, which is increased to $500 when Comic Book Guy learns that the artist in question is dead. Knowing she could never afford it, Lisa sinks back into despair, only for help to arrive from the aspiring lepidopteran arsonist, whose recent traumatic experience with that piece of jagged metal has brought him a cash settlement of precisely $500.
Bart's subplot, which involves him falling ill after unwittingly ingesting the cereal prize from Hell and requiring emergency surgery, is (in spite of its gruesome premise) predominantly there to bring comic balance to a more sombre than usual A-story. It is, though, no arbitrary joke-fest, with the resolutions to these respective stories dovetailing in a way that is meaningful and rewarding. As fate would have it, Bart's swallowing of the metal hoop occurs on a morning before a history test that he's ill-prepared for; when he starts to complain of intense pains in his stomach, Marge and Homer, wary that he's pulled this exact shit to get out of a test before, pack him off to school, although Lisa voices the opinion that his illness might be genuine this time. This in itself feels like a nice callback to the events of "Bart Gets an F", where Lisa was the only character who knew that Bart was faking his amoria phlebitis; it speaks volumes to their sibling connection that she's consistently able to tell the difference. When Bart finally receives a settlement from Krusty (lawyer Lionel Hutz has actually scammed him out of a much more substantial sum, but $500 seems like a huge amount to the trusting eyes of impressible youth), he's all prepared to blow it on the most frivolous purchase imaginable - a limited edition pog (remember those?) with Steve Allen's face on - but his conscience prevails and he instead buys Lisa the elusive album (the sequence detailing Bart's dilemma, which repeatedly shifts between three different leitmotifs, is in itself such a wonderful testament to Clausen's composing talents). He explains to Lisa that he felt he owed it to her for being the only person to take his side when he got sick. It's a lovely gesture that upholds my personal view of Bart and Lisa having the strongest bond out of all of the Simpsons, but it has deeper significance still, as a final affirmation to Lisa that, even with her soulmate sadly departed, she does not have to worry about being alone in the world. No matter what, she can always count on her family to come through for her.
At last the time has come to dig into that bizarro finale. Even with that copy of Sax on The Beach safely within her mits, Lisa's tribute seems doomed to fall at the second hurdle, that being K-jazz's ridiculously weak broadcast range; even when standing immediately outside the station with a portable radio, she is unable to pick up their transmission of Bleeding's music. That is until a thunder cloud appears in the sky, and a bolt of lightning strikes the K-Jazz antenna, making it so powerful that the broadcast is heard and enjoyed all over Springfield. The Deus ex Thunder Cloud subsequently assumes the form of none other than Bleeding himself, assuring Lisa that her actions made him happy. This much is a parody of the sequence from Disney's The Lion King in which the deceased Mufasa appears amid the night sky and urges the emotionally lost Simba to remember who he really is - a point made salient in having the ghost of Mufasa appear right next to Bleeding, with a message for Simba...or does he mean Kimba? (On the DVD commentary, Jean and Reiss fret that this is a jab that nobody would have gotten after the 90s, but they'd no need to fear - as long as there are animation buffs in this world, that line will always be hilarious and relevant.) They are then joined by the ghost of Darth Vader, making his shocking declaration of kinship with Luke, and then finally...James Earl Jones, giving an announcement on behalf of CNN? This elaborate and totally nonsensical gag is nothing less than a loving tribute to the vocal talents of Jones, who voiced Mufasa and Darth Vader and recorded announcements for CNN. (Jones was imitated here by Harry Shearer, although he had previously guest starred in the Halloween episodes "Treehouse of Horror" and more recently "Treehouse of Horror V". Somewhere out there there's also a parallel universe in which he got to voice Sideshow Bob.) It's a sequence that would seem perfectly suited to the looser, cinema-fixated reality of The Critic, but if feels just a whisker out of place in The Simpsons, no? Don't get me wrong. I love the idea of Bleeding, Mufasa, Darth Vader and James Earl Jones all being besties in the afterlife (Jones himself was very much alive when "Round Springfield" initially aired, but now in 2025 his placement alongside these deceased characters seems less absurd). But what exactly are we to make of this sequence within the context of this otherwise relatively grounded story about grappling with bereavement? Surely Mufasa, Darth and then-still-with-us Jones didn't literally manifest in the clouds above Lisa? Surely not even Bleeding was really there, jamming with Lisa to a "Jazzman" reprise? I recall that Groening made a big thing about that catfish who winked at the camera in "The War of The Simpsons", but that all seems very sensible and subdued compared to the borderline fever dream unfolding here.
"Round Springfield" leaves us with a head-scratcher - have the skies above Springfield really become host to this odd assortment of spectres (most of them culled from popular culture), or is the entire sequence nothing more than a weird and protracted bit of symbolism? Arguably, there was precedent for it in "Old Money", which included a scene in which the ghost of Bea Simmons appears to Abe on a rollercoaster, though its strangeness was of a somewhat lower-key variety and was easy enough to rationalise as representing some kind of internal monologue on the part of Abe. It should also be noted that the Disney moment it's parodying is up for a similar kind of interpretation - Rafiki makes a remark about the weather, leaving some ambiguity as to whether Mufusa's manifestation really occurred, but anyone over the age of 14 would presumably be more inclined to read it as symbolising the soul-searching Simba undertakes in trying to understand what Rafiki means by "He lives in you." It's possible that this too is taking place inside of Lisa's head, but it goes so far with some of its concepts and gags that I fear it all makes Lisa look just a little unhinged.
It is, though, a magnificent ending - triumphant, redemptive, uplifting and poignant. Perhaps it doesn't matter how well it meshes with the series' reality or what sense we make of it, so long as we gather that Lisa has reached the light at the end of the grieving tunnel and realised that she retains her connection to Bleeding Gums and everything that he taught her. I would argue that the intention here is nothing more complicated than to leave us on a spectacular emotional high following such a downbeat experience - it's the episode's markedly eccentric way of letting us know that everything is going to be okay. It helps that Lisa and Bleeding's recurring performance of "Jazzman" is allowed to be a thing of beauty in itself, tussling only with the "Oh Streetcar!" material from "A Streetcar Named Marge" for my favourite musical sequence of all the series (bless the person who compiled the Songs in The Key of Springfield album for putting those tracks right next to each other, so I could listen to them over and over in easy succession). Perhaps it ought to lose the edge for not being an original song, but that seriously doesn't matter. They imbued it with a heart and an aching all of its own. I love Carole King's original 1974 rendition too, but thanks to The Simpsons I will forever interpret it as being about Lisa's yearning to become one with her idol, both before and after his passing.
Cheers to Yeardley Smith, to Ron Taylor and not least to Alf Clausen for making this episode such a transcendental voyage. Jeers to Disney, for a whole multitude of reasons, but in particular for the downright galling manner in which, while watching this episode on Disney+, they always seemed to want to take out midway through the credits and directly into "The Springfield Connection", rather than encouraging me to enjoy the whole dazzling performance of "Jazzman" as the Simpsons gods intended. If Disney had their way, nobody would stick around for the punchline that rounds off the story: "Oh come on, Lisa, I've got a date with Billie Holiday!" Bleeding's parting words, and they couldn't give a mouse's soiled gloves if you hear them. The sacrilege astounds.