History YMMV / WithBigShellsAndWings

* ItGetsBetter: The story starts out as a comical fanfic suited for young teenagers. But the further along it goes, the darker it becomes and the more serious the plot is. Some of the tasteless jokes also begin to go away as the story progresses, and many characters start to go through seriously needed CharacterDevelopment. By the time chapter 37 comes around, the story arguably starts GrowingTheBeard.

* CompleteMonster:
** Dracolin, a sadistic dragon who enjoys burning, torturing, devouring, and tormenting others [[ForTheEvulz just because it's fun]]. What's mostly disturbing about Dracolin is that he takes pleasure in scaring little Yoshi children, almost to a point where he comes across as a pedophile. He even crushes one of them to death and then brags to the dead Yoshi's friends how wonderful it felt killing her. To top all that off, it's implied more than once that Dracolin has a {{Fetish}} for ''crushing small creatures''.
** Trowzer is Bowser’s sadistic half-brother and the BiggerBad of the fanfic. [[EstablishingCharacterMoment He opens the story]] by implying that he plans on taking over his brother’s empire, and makes good on his promise when he begins to convince several of Bowser’s troops to turn against him with bribes and promises of being more than minor lackeys. Some who stay by Bowser’s side or try to uncover Trowzer’s evil plans are promptly killed, some of whom were murdered by Trowzer himself. After Geno, Kooper, and the Mario Bros. are captured by Trowzer thanks to [[TheMole Blaze]], [[YouHaveFailedMe he murders Blaze in cold blood for failing him earlier]], saying that he was merely [[TheSociopath an object that broke and needed to be replaced]]. Once the Mario Bros. escape, Trowzer encounters them again and [[NoHoldsBarredBeatdown effortlessly bests both of them]], and keeps them alive solely to torment them even further. He then leads an assault on Bowser’s castle, where he and his army slaughter hundreds of his troops—including Larry Koopa, whom Trowzer messily tortures and beats to death after Larry refuses [[DefiantToTheEnd to cry and beg for his life]]. When Trowzer finally confronts Bowser, [[KickTheDog he taunts him by gloating about how glorious it was torturing Larry]], and he [[spoiler:successfully kills his half-brother and [[TheBadGuyWins claims his throne in the end]]]]. While first presented as a [[DangerouslyGenreSavvy darker, smarter version of Bowser]], Trowzer is no more than [[VileVillainSaccharineShow a disturbingly vicious villain for a story that started off being very lighthearted]].

** The Koopa Bros. inadvertently crossed it when they [[spoiler:blew up the defense facility that protected Yoshi's Island. That means they're indirectly responsible for the massacre that Trowzer sanctioned there]].

* CompleteMonster: Dracolin, a sadistic dragon who enjoys burning, torturing, devouring, and tormenting others [[ForTheEvulz just because it's fun]]. What's mostly disturbing about Dracolin is that he takes pleasure in scaring little Yoshi children, almost to a point where he comes across as a pedophile. He even crushes one of them to death and then brags to the dead Yoshi's friends how wonderful it felt killing her. To top all that off, it's implied more than once that Dracolin has a {{Fetish}} for ''crushing small creatures''.

* CompleteMonster: Dracolin, a sadistic dragon who enjoys burning, torturing, devouring, and tormenting others [[ForTheEvulz just because it's fun]]. [[ArsonMurderAndJaywalking Plus he likes grossing out others with childish scatological humor]]. What's mostly disturbing about Dracolin is that he takes pleasure in scaring little Yoshi children, almost to a point where he comes across as a pedophile. He even [[spoiler:crushes one of them to death and then brags to the dead Yoshi's friends how wonderful it felt killing her.]] To top all that off, it's implied more than once that Dracolin has a {{Fetish}} for ''crushing small creatures''.

* BigLippedAlligatorMoment: Chapters 35 and 36. Mario and his friends enter a series of vortexes that transport them to various stages and mini-games that the Mario Bros. have been to in previous adventures. [[MindScrew Um, okay then.]]

* MoralEventHorizon: Trowzer arguably crossed it multiple times, but it wasn't until [[spoiler:he murdered Yellow]] that he blew away his chances at redemption.

* NightmareFuel: Trowzer disecting a koopa troopa alive ''in front of Dix'' just so he'll persuade him to stop asking questions about his personal business. The author even put up a warning at the beginning of the chapter.
* {{Squick}}: The last scene in chapter 20, which more than likely left the readers gagging.
* TearJerker: [[spoiler:Yellow's death]], for starters. It didn't help that [[spoiler:Red was so traumatized by the event that he became a sobbing, drunken wreck]].
** [[spoiler:Dix's death]]. Made all the more heartwrenching that he was a minor character who just earned his MauveShirt status and spent his final moments desperately trying to run away to safety.

* CompleteMonster: Trowzer and some of his chief henchmen.