Episode - 2F24\\
First Aired - 4/30/1995

In this partial VerySpecialEpisode, Lisa discovers that her friend and jazz mentor, Bleeding Gums Murphy, is in the hospital, and when he dies on the night of her recital, Lisa works to keep the musician's memory alive. Meanwhile, Bart comes down with appendicitis from eating Krusty the Clown's new cereal, which comes with a jagged metal "O", and sues the clown for personal harm.
!!This episode contains examples of:

* AffirmativeActionGirl: In-universe, Krusty's forced to add "Ms. No-Means-No" to his cast due to an expensive sexual harassment suit. Krusty [[WhatAnIdiot immediately hits on her]].
* AmoralAttorney: Lionel Hutz pretty much stole all but $500 of Bart's $100,000 settlement.
* ArtisticLicenseMedicine: Eating jagged metal doesn't cause appendicitis. It would have given Bart horrible internal bleeding and possibly killed him, but that's not very family-friendly, is it? It doesn't help that an actual medical consultant (who was related to Al Jean) was called in for the show and the writers had to resort to a ridiculous excuse to make Bart come down with appendicitis.
* BecauseYouWereNiceToMe: Bart buys Lisa the rare Bleeding Gums Murphy album because she was the only one to believe he was really ill.
* BitingTheHandHumor: In-universe, Krusty accidentally does it when he speaks ill of Percodan in his show right before learning that the company that makes it became his new sponsor.
* BlindMusician: Bleeding Gums' mentor, Blind Willie Witherspoon. {{Subverted}} in that, for 30 years, he thought he was playing the saxophone...''when he was actually playing an umbrella.'' No one said anything because they thought it was funny.
* CallBack: After the news of Bleeding Gums' death, Lisa cries on the bridge [[Recap/TheSimpsonsS1E6MoaningLisa where the two first met]].
* CassandraTruth: No one except Lisa believes that Bart is truly sick, knowing his tendency to try to get out of tests. Though Marge was close to believing Bart too.
* CheeseEatingSurrenderMonkeys: TropeNamer. Groundskeeper Willie, due to budget cuts, is forced to teach French, and he calls the students this.
* CrazyPrepared: Springfield Elementary's school charter states that no teacher is to be held accountable if Bart dies or if Milhouse gets eaten by the school snake.
* DeadArtistsAreBetter: Lisa finds Bleeding Gums Murphy's only album at Comic Book Guy's store, costing $250. But when Lisa mentions that Bleeding Gums has recently died, [[KickTheDog he immediately doubles the price to $500]].
* EmbarrassingTattoo: See TakeThat.
* GamblerGroupies: Bart has an ImagineSpot in which he's in a casino, surrounded by attractive woman.
* HereWeGoAgain: Bart plans to re-earn the $500 dollars he spent on the jazz album by suing the Krusty corporation over their ''new'' Krusty-O's cereal...with flesh-eating bacteria.
* ImagineSpot: Bart has two: what he could do with $500 (losing it immediately on roulette) and torching the school after he's reincarnated as a butterfly (and watching Principal Skinner get blamed for it).
* IncurableCoughOfDeath: Bleeding Gums.
* ItAlwaysRainsAtFunerals: Although it clears up when Lisa decides to find a way to honor Bleeding Gums' memory.
* LastDisrespects: No one showed up at Bleeding Gum's funeral because no one knew him.
* LightningCanDoAnything: Like increase a radio station's broadcasting range.
* LongLostRelative: Apparently, Bleeding Gums and Dr. Hibbert are brothers... [[MissedHimByThatMuch not that either of them realize it]].
* NiceJobBreakingItHero: Homer tries to comfort Lisa when she cries over Bleeding Gum's death. Only to say something stupid which made her feel worse.
-->'''Homer:''' Oh, I blew it again. ''(Maggie puts her pacifier into Homer's mouth)'' Mmm...
* NoOSHACompliance: Krusty's cereal had ''metal'' in it. Krusty ends up in severe pain just by eating a regular piece of cereal.
* OOCIsSeriousBusiness: Mrs. Krabappel only believes that Bart's really in pain when he completely finishes his test before asking to go to the nurse again. She still lets him suffer a few more seconds of pain before sending him off, though.
* RunningGag: The hot-dog vendor that always shows up at events where Homer wants a hot dog.
-->'''Marge:''' [[LampshadeHanging What do you do, follow my husband around?]]
-->'''Vendor:''' Lady, he's putting my kids through college!
* ShoutOut:
** Bleeding Gums was a special guest on ''Series/TheCosbyShow'' in 1986. The scene parodies the fact that quite some famous jazz musicians like Music/DizzieGillespie, Music/TitoPuente[[note]]who himself appeared in ''The Simpsons'' later on[[/note]] and Music/LenaHorne were once guests on the show. It also references Creator/BillCosby's tendency to clown around, talking gibberish and focus most of the attention to himself, exaggerated here to the point that Bleeding Gums doesn't even have a line.
** Bleeding Gums appears in the sky to Lisa, together with Mufasa from ''WesternAnimation/TheLionKing'', Darth Vader from Franchise/StarWars and Creator/SteveAllen saying ''This is CNN'', all references to the fact that Creator/JamesEarlJones voiced these characters.
** The song ''Jazzman'' by Music/CaroleKing is covered by Lisa and Bleeding Gums near the end of the episode.
** Bleeding Gums mentions he's ''got a date with Music/BillieHoliday''.
** The episode's name is a reference to '''Round Midnight'', a film about an unappreciated jazz musician, which got its title from a jazz standard by Thelonious Monk.
* SuckySchool: This episode truly shows how bad Springfield Elementary is (along with this season's "The PTA Disbands").
** The school's charter has a rule stating that they are not responsible if Bart dies ([[TheChewToy or if Milhouse gets eaten by the school's pet snake]]). Bart ''can'' be a bad student at times, but having a rule stating that is straight up "Boys of Bummer"-style cruelty against Bart.
** Lunchlady Doris works as Springfield Elementary's nurse due to budget cuts (even though "Whacking Day" revealed that Lunchlady Doris took the school nurse job so she can get two paychecks).
** The very Scottish Groundskeeper Willie is now a French teacher.
* TakeThat
-->'''Homer:''' Lisa, honey, if you really wanna preserve his memory, I recommend getting a tattoo. It preserves the things you love...(Homer rolls up his sleeve to reveal a heart with the words...) "Starland Vocal Band"?! They ''suck''!
** "You must avenge my death, [[Manga/KimbaTheWhiteLion Kimba]]...dah, I mean ''[[Disney/TheLionKing Simba]]!''
** One against New Coke, in Bleeding Gum's flashback, courtesy of Creator/BillCosby.
-->'''Crosby''': "Jazz is like the New Coke. [[TemptingFate It'll be around forever]]."