I shouldn’t be as astounded by how this show constantly finds new depths to its protagonists at this point. ‘Character development’ can mean one of two things, and it’s not often immediately clear which version people mean when they use it – it can mean either a character changing (usually, meaning positive growth), or it can mean revealing a different facet of the character. As a product of early Nineties television, The Simpsons can never fully embrace the first kind, although there is always a sense that the character has learned something within episodes. This show’s big emotions are always tied into some hidden strength of the character emerging, and that’s usually something that stays with them even when the specific events are never referenced again (see the progression of Homer’s sacrifices for Lisa progressing from “Lisa’s Pony” to “Lisa The Beauty Queen” to “Homer The Vigilante”, and further when we get to “Lisa The Iconoclast”). In this case, we and Lisa discover her capacity to handle grief when her hero, Bleeding Gums Murphy, comes back into her life only to pass away. Lisa is always at her best, comedically and dramatically, when she has at least one foot in being a kid, and I’m struck by how kid-like her grief is – this is the worst pain she’s ever experienced, and she’s totally unprepared to deal with it (“Why does it keep hurting?”). Luckily, effing the ineffable is what Lisa does best; she won’t ignore her grief or try to put it aside. For once, Marge actually provides a solution too, convincing her to honour Bleeding Gums’ memory by playing his album. It’s not enough to identify our emotions, we have to have an expression for them, too. Preserving people’s memories is as much about soothing ourselves as it is serving the dead.

Bart’s story is a countermelody to this as opposed to riff on the same theme; it plays on Krusty’s terrible product placement a la “Kamp Krusty”. This feels like a logical outcome of Krusty’s total cynicism with the entertainment industry, the real world consequences to the episodes delving into his inner life. If you like, icons of industry like Krusty pass their dysfunction down to the consumer in strange, unexpected ways, until his negligence is literally tearing up Bart from the inside. I was a bit wary of the sexual harassment suit gag at the start, but it ends up in this weird place where it’s neither condoning nor condemning the concept, just using it as fodder for jokes as Krusty blunders his way through (“Percodan?!”). In terms of Bart, this is a great Boy Who Cried Wolf situation that doesn’t have a literal wolf involved; it’s not a thematic riff but there is the same sense as in Lisa’s story of characters gaining meaning like a snowball falling down a hill. Bart spending the money from his lawsuit is kind of a cheap way of finishing up the story in a sentimental way, but it has the triple-duty of finishing Bart’s story, advancing Lisa’s story one step, and helping me find an end to this paragraph.

(Bart also gets two separate hilarious imagination sequences. Losing all his money at roulette and thinking that’s cool is funny, but I would push “Nobody ever suspects the butterfly” as the funniest peek into Bart’s imagination)

But obviously, this is Bleeding Gums’ episode. His little arc lets the show parody the rise and fall of a rock star again, and I love that Lisa observes “the moral seems to be that a lifetime of jazz leaves you sad and lonely.” One of the side effects of the show consistently refusing to give any of its characters an easy, sitcom-style win is that hard work becomes its own reward; it ties in with the show’s twin themes of spiritual fulfillment being better than material success and lack of material success really sucking. That makes it interesting to me that the episode ends with not one but two of the cheesiest moves the show has shot for so far, with the jazz station getting a bolt of electricity that sends Bleeding Gums’ music into every radio station in town and Lisa getting one last jam session with him, and that this somehow totally works. On one level, I think it’s because the show so rarely goes to this well that it means something when it does, like a rock song pounding on the I chord long enough to make jumping to the IV chord a release. But it also feels like this is the one thing the show is willing to cut the characters some slack on. Death is a difficult thing for any eight year old to process, even one as precocious as Lisa. The show is okay with giving her some release from that kind of pain.

Chalkboard Gag: Nerve gas is not a toy.
Couch Gag: The family are all different sizes.

This episode was written by Joshua Sternin and Jennifer Ventimilia (credited under her deadname), and directed by Steven Dean Moore. It was based on a story idea by Al Jean and Mike Reiss, coming back to lessen the workload and bringing much of their staff (including Sternin and Ventimilia. This is the first episode in which any character dies. The funniest bit of animation is Krusty eating the non-dangerous Krusty-O.

This episode is full of what TV Tropes calls Brick Jokes, with my favourite being the already hilariously dumb gag of Dr Hibbert good-naturedly agreeing to take out all the kids’ appendices coming back when the school orchestra is almost entirely empty because of it, closely followed by Steve Allen cameoing and then turning up in Pog form.

The title is a reference to “‘Round Midnight” by Thelonius Monk. When Bleeding Gums comes back as a cloud, he’s joined by Mufasa, Darth Vader, and James Earl Jones announcing for CNN, all of whom are roles made famous by James Earl Jones (especially that last one) but here are impersonated by Harry Shearer. Mufasa accidentally says “Kimba” instead of “Simba” at first, referencing the controversy that The Lion King ripped off Kimba The White Lion. Lisa and Bleeding Gums play “Jazzman” by Carol King. Bleeding Gums has a date with Billie Holiday. In life, he appeared on The Cosby Show. Lionel Hutz’s crack team of lawyers includes parodies of Robert Shapiro and Alan Dershowitz, OJ Simpson’s lawyers. Blind Willie Witherspoon combines the names of Blind Willie McTell and Jimmy Witherspoon.  

Iconic Moments: 3. “Bonjourrrrrrrrrrrrrrr, ya cheese-eatin’ surrender monkeys!” | “That’s some nice flutin’, boy.” This is one of those Simpsons gags where I don’t think people remember and repeat the specific gag so much as the construction of the sentence. | “Part four of our series on the agonising pain I live in every day.”
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