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The opening has Bart and Lisa compare Halloween candy yields. Lisa has more than Bart, but that's not enough- she steals one of his. Bart starts choking Lisa, who breaks a pot on his head. He then tries to stab her with a poker, but gets Homer instead. Homer is very upset about this, and tries to attack them with a log from the fireplace. The log instead lands in Grandpa Simpson's lap, setting him on fire. He remarks that he's still cold. Homer then rolls the kids up in the carpet, and tries to bash them with a club. Marge come in and disagrees with Homer's approach by using a shotgun. Homer's bloodstains on the wall behind him spell out ''Treehouse of Horror XIV''.

! Reaper Madness

Death knocks on Homer's door. He's come for Bart. Marge tells Bart to run like the wind (which she pronounces as 'wined' until corrected by Lisa). Cue ScoobyDoobyDoors, set to Yakety Sax. Eventually, Death corners Bart and pins him to the wall. But before he can kill Bart, Homer kills him. Bart is saved. However, Death has an important duty. Without him, ''The Jim Belushi Show'' will never be canceled, a man shot up by the mob will never die no matter how many holes they put through him, and Moe is getting very bored after hanging himself.

Homer mourns Death, and Marge tells him to just take Death's body out to the curb, as it's trash day. Homer does so, emptying Death's robes out into the trash. He notices that the robe's pretty soft, and tries it on himself. He then shows it off for his family. But as he does so, one of his hands withers and becomes skeletal. Death's scythe and 'To-Die' list materialize in his hands. Homer is going to be the new Grim Reaper. He tries to refuse, but the robe convinces him not to- via GroinAttack.

Homer settles into his job, and eventually grows to enjoy doing it- at least until the next person on his list is Marge. He is horrified, and later goes up to God with her corpse to beg God to let him give up the job. God does... and then finds out that the corpse was actually one of Marge's sisters with Marge's beehive taped to her head. He chases Homer, but gives up.

Homer enjoys a family dinner with the now short haired Marge.

! Frinkenstein

Professor Frink is a MadScientist trying to build a corporeal body for the spirit of his dead father (played by none other than the inspiration for Professor Frink's character, Jerry Lewis). Of course, his reanimated father goes on a rampage, forcing Frink to stop him.

! Stop the World, I Want to Goof Off

Bart and Milhouse find an ad for a time-stopping watch in one of Marge's old comics. They buy it, and find out that it does work exactly as advertised. Pushing the button on the top will cause time to stop, with anyone holding onto the watch being unaffected. The pair use it to go on a town-wide pranking spree. They take Homer's donuts out of his hand (and when he tries to commit suicide, replace the knife with a banana), pull Principal Skinner's pants down, and otherwise screw around with the townspeople.

Of course, people notice, and a meeting is called about the mysterious pranks. The sign suddenly changes several times, but there's a good turnout there. The mayor takes the podium to discuss what's been happening, while Bart and Milhouse prank him by putting him in weird costumes.
->'''Mayor''': People, Springfield is in crisis. Fingers have been shoved up noses, pants have been pulled down, and [gets put in a French Maid costume] mayors [American Colonial costume] have [Viking costume] been [horse costume] repeatedly [giant sandwich costume] humiliated. Damnit!

Unfortunately for the pranking pair, the Mayor is one step ahead of them, and he has a plan.
->'''Mayor''': I thought our mysterious pranksters might be here tonight, so I covered the meeting hall with ultraviolet powder. [flips switch] Behold, the perpetrators!

The lights turn off, and what do you know, there are glowing footprints leading right to Bart and Milhouse. The crowd runs after them intent on payback, and Bart and Milhouse have to quickly escape from the angry mob. Bart manages to get out the magic watch, and he and Milhouse stop time together. Just in time, too- a bullet from Wiggin's gun was just about to hit them. Unfortunately, the watch breaks, trapping both kids in stopped time.

Milhouse is happy about it- now he's the second-coolest kid on Earth! Bart is more upset about it at first, and then realizes that it means that they can do ''anything'' they want. Steal money, museum pieces, and famous artworks? Sure. Live on candy? Why not. Keep Bart's family in his house as statues? It's not like they can complain, even when Bart accidentally knocks Homer's head off. Turn celebrities into punching bags? Probably the most use anyone's gotten out of them. Give the Pope wedgies? He can't stop them. Play naked basketball? [[EveryoneHasStandards Nope, they won't be doing that]].

Eventually, Bart gets rather tired of that life. He misses being a regular kid, getting hugs from his mom (who's currently serving as the stand for a basketball hoop in the kitchen). Milhouse thought he would be happy now that his parents back together, but it's kind of hollow since 'back together' meant 'tied up together with ropes'. They get a book on watch repair, which says they can learn it in 8 1-hour lessons.

Fifteen years later, Bart and Milhouse have finally repaired the watch. But before they re-start time, Bart realizes that if the town sees what they've done, they'll kill the two anyway. They give the mob a scapegoat in the form of another kid, and then re-start time. The mob chases the kid and beats him to a pulp.

Back at the Simpsons' home, Marge wonders why Bart is so tall and shaggy. Homer thinks it's just another one of life's mysteries, like why Homer's nose is jammed with plastic soldiers. Lisa says that it's because Bart used his magic stopwatch to stop time. Bart asks if she's jealous. Lisa is. At Homer's urging, Bart lets Lisa borrow the stopwatch. [[WhatDoesThisButtonDo Lisa gets curious about what a different button on the watch does]], and presses it.

What it does is gives the Simpsons other than Lisa rocket torsos. And when she presses it again, it turns them into opposite-gender versions of themselves. Further presses turn them into bobbleheads, magazines, [[ComicBook/FantasticFour the Fantastic Four]], and then into their normal selves (with Bart being 8 years old again), but spinning around hula hoops.
->'''Homer''': Okay, that's good. Stop there.

This was the first "Treehouse of Horror" episode to ''officially'' be titled "Treehouse of Horror", as every prior special had officially been titled "The Simpsons Halloween Special", and the previous special was titled "The Simpsons Treehouse of Horror".

!! Tropes:

* AndThisIsFor: When Homer killed the Grim Reaper, he said it was for Snowball and Kennedy.
* AnythingButThat: When Homer realizes Marge is supposed to die.
* BatmanGambit: The Mayor pulls one off to expose Bart and Milhouse as the ones pranking Springfield, betting on them not being able to resist pulling pranks at the meeting.
* BeCarefulWhatYouWishFor: At the end of the final segment, when Lisa realizes what Bart has been doing with the stopwatch, she asks, "Why can't I tinker with the fabric of existence?" Homer has Bart give her the stopwatch, and she notices a red button on it. She presses it to see what it does, only for the rest of the family's bodies to split into rockets. She ends up changing them multiple times, trying to correct her error.
* BigNo: Homer's reaction upon the idea of a world without death meaning [[TakeThat Jim Belushi would never be cancelled]].
* TheBusCameBack: The "Scary Names" for the credits return after being absent for 2 Halloween specials. [[https://frinkiac.com/img/S15E01/1267265.jpg Al Jean's "Scary Name" credit lampshaded this.]]
* ClothesMakeTheSuperman: Putting on Death's robe makes Homer the new Grim Reaper.
* {{Fanservice}}: A female crossing guard in Sweden is depicted working completely naked for no reason.
* FantasticIndifference: The pizza guy delivering to Moe's doesn't seem to care that Moe was hanging from the ceiling.
* GilliganCut: The watch repair book says that Bart and Milhouse can learn watch repair in 8 1-hour lessons. It takes them fifteen years.
* GlowingEyesOfDoom/RedEyesTakeWarning: Death.
* {{God}}: He tries and ultimately fails at chasing Homer, only for him to give up and to admit that he's "too old and too rich for this."
* GroinAttack: That was how the Grim Reaper's robe forced Homer to take on the job.
** Ditto on how Frink kills his re-animated father.
* LaserGuidedKarma: Happened instantaneously to Nelson, who Bart and Milhouse bring into the scene to laugh at a naked Homer, only for ''his'' clothes to disappear before he can finish his SignatureLaugh.
* MajorInjuryUnderreaction: Homer in the opening after he's stabbed in the chest with a poker. And Grandpa's only reaction to being set on fire is to remark that he's still cold.
* NakedPeopleAreFunny: Bart and Milhouse steal Homer and Nelson's clothes at one point while stopping time.
* OminousLatinChanting: When Death has pinned Bart to the wall with his scythe.
* RuleSixtyThree: [[https://frinkiac.com/img/S15E01/1252876.jpg Briefly happens to Homer, Marge, Bart, and Maggie]] when Lisa keeps messing with the watch at the end. On the upside, this is the first change that restores Bart to his original age.
* ScoobyDoobyDoors: As Death tries to take Bart, he gives him chase, setting up a hilarious game of this, complete with [[Series/TheBennyHillShow "Yakety Sax"]] to top off the scene.
* SuicideAsComedy: After realizing all of the doughnuts in the break room keep disappearing before he gets a chance to eat them, Homer decides to stab himself in the stomach...only for the boys to replace the knife with a banana at the last second.
* TakeThat: The aforementioned BigNo example regarding Jim Belushi.
** Kang and Kodos think humans are silly for showing a Halloween episode in November (a reference to how the Treehouse of Horror episodes weren't being shown around Halloween from seasons 12-20 due to Fox's rights showing the World Series games. It wasn't until "Treehouse of Horror XX" in season 21 that they'd start airing around Halloween again.).
* TouchOfDeath: Homer as Death.
* WhatDoesThisButtonDo: When Lisa gets the stopwatch, she gets curious over its red button. She ends up repeatedly changing the other Simpsons with each press of the button.