85,85,55,44. I don’t know who 85 is, but they must be having a really bad day

Both of Twilight’s parents, Diamond Tiara, and Spitfire.
 
I’d assume Twilight Velvet would be the fear of losing Twilight Sparkle to monsters then night light being losing Velvet. Diamond Tiara will be returning back to her insulting days and left behind. Spitfire not living up to being a good leader. Then me, being so close to rusty nails and poisonous insects.

Tank, Gilda, Upper Crust, and Braeburn…?
 
Welp, Goodbye Good Ending, Hello Sadness…!

I think you need to explain better cause I don’t think you can get to some of the pieces.

Well that works well enough. I’m not sure if she knew it was dangerous or not though. I’d have to rewatch the scene where she talks about it.

@Keyintheshoe  
Spitfire approved of Lightning Dust making a dangerous tornado to get rid of clouds.

Hoity Toity being Ted makes sense.  
Spitfire being Benny could work. I’m not sure how much military work wonderbolts do, much less how much Spitfire would do.
 
Looking at the game’s intro it looks like it implies Gorrister is a wife beater.  
Though looking at a gamefaq, it seems that is not the case, and it seems that the sin is just not stopping people from letting his wife go to the asylum because he was too much of a pacifist.
 
Though Cadence could totally cheat on someone. As someone who spreads love all the time, she probably wouldn’t understand why society would dislike people cheating, at least not at first. She probably learned from her mistake, but the damage would have been done.
 
 
I don’t think we’re going to get anyponies to fit ellen (sexist) or Nimdok (nazi gasser).  
Unless you want to equate Nightmare Moon with Nimdok, since they both deal with slow ways of killing masses of people (NMM is implied to slowly starve ponies because of lack of sunlight to grow crops).
 
As for Ellen, I’m not sure of any outright sexist ponies.

@Keyintheshoe  
So Hoity is Ted and Spitfire is Benny?
 
Maybe Cadance cheated on Shining Armor, or was falsely accused of something bad that happened to him, like Gorrister.

Braeburn’s horrible sin is being a part of the town that messed up the buffalo migrating pattern. Though he helped fix that later right? Or did it get fixed without his help? That’s all I have off the top of my head, since I only remember him greeting the Mane 6 at the start of the episode.
 
I’d be surprised if Hoity Toity didn’t exploit someone somewhere to get as rich and famous as he did.
 
Cadence may have cause some people to fall into love soo much that they lost touch with their other priorities in life. Like paying bills, going to work, etc. Ruining their lives. Cadence may have done this when she was practicing her magic and/or wanted to test how powerful love can be.
 
Spitfire’s sin would probably be something along the lines of pushing somepony too hard, that it caused them to be severely injured or die. Or that she had a chance to rescue somepony, but didn’t because she was angry at that pony for some reason (maybe even if it was that pony that was causing other life threatening situations for other ponies)

I might do a reroll myself.
 
Me, Braeburn, Hoity Toity, Cadance and Spitfire are being tortured by AM. I’m not sure what our horrible sins are though.

@Keyintheshoe  
Thunderlane has the horrible sin of falling in love with an inanimate marshmallow.

Since you have called for a re-roll, I’d be glad to do so!
 
Whoever 96 is (thunderlane?) - Dunno anything about him  
Winona - lolwut? Horrible sin of….. being a dog? Defiling people’s property with dog doo doo? =p  
Woona - Horrible sin of being NMM  
Lyra - Horrible sin of doing something related to human hands? shrug  
Wait… Lyra, did you bring back AM because it knew about humans!??!
 
 
As for fighting AM. Woona would probably save the day there, since she’s an Alicorn and all. Though I don’t know the full extent of AM’s powers.  
Lyra might know a way to disable AM because of her obsession with humans, so she’d figured out a way to defeat AM because she knows how AM thinks because AM was made by humans?

@Niggoslav_Krawczyk
 
@Keyintheshoe
 
…  
Reroll.

@Keyintheshoe  
How do you not remember the best Appleoosan? How dost thee forsaketh Cherry Jubilee? ShAMEFUR DISPRAY, COMMIT SUDOKU!!!
 
I got Silver Spoon, Discord, Gummy, and Rarity. Seems like a fair fight, actually. PREPARE THY ANUS, AM!

Spitfire, Cloud Chaser, Blinkie, and Screw Loose.
 
I think that’s a good team.

Mayor Mare  
Granny Smith  
Doctor Whooves  
Whoever 92 is
 
Now I have only seen the intro to the game, but aren’t they all supposed to have some major sin that they commited?
 

 
Granny smith and the Mayor have lived long enough that they must have done some horrible thing in their life. The question is, what?
 
Anyone that watches the Doctor who series will see him getting accused of being evil all the time (or at least in a lot of the episodes I watched)
 
Well, on the bright side, the Doctor will get us out of this right?

Cloudchaser, Featherweight, Pumpkin Cake, and Pound Cake.

@Wafflecannon  
Protect her or I will LET AM turn you into the great soft jelly thing.

@Randomosaur  
I guess that could work, but I was thinking more along the lines that Benny was mentally disabled, and since her intelligence is something Twi cherishes taking it away would be something AM would do.

@Wafflecannon  
>>245987?

10,14,15,71  
Twilight, Twilight’s Dad, Doughnut Joe, and Vinyl
 
I’m imagining a fate really similar to Benny’s for Twi.

@Randomosaur  
Oh, don’t worry. I did. I always add myself to these kinds of scenarios.

So that’s a hundred characters…

@Dream_Seeker  
I am a great Hugh Jelly thing.

Diamond Tiara  
Photo Finish  
Lily  
Hugh Jelly  
… what do I have to say about that?