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EqG Sombra is an escaped mental asylum patient.
 
Discord is the superintendent of the school system.
 
Chrysalis is a convicted con-artist in the EqG universe.

-It is custom of earth ponies to dine at the graves of loved ones to show respect.  
-Trixie grew up in a traveling circus. Her father was the ringmaster. Her mother was the daughter of the seer he hired.  
-Trixie is actually a zony, and hides her stripes.  
-The alicorn amulet has the soul of an alicorn trapped inside. The corruption is a result if it’s growing anger over its imprisonment.  
-Sombra likes reptiles, especially snakes. His cape is made up of a bunch of red snakes, and one large black and white snake.

@gasmaskangel  
So, Mentally Advanced Twilight?

@gasmaskangel  
going to add to this  
Twilight can drink enough to put down 2 full grown dragons and just be slightly tipsy

The mirror in EG is the portal to a fake realm that is crafted by the psyches of every creature that has entered it before.

Twilight is an alcoholic. Nopony notices this because she does all her drinking alone, and Spike doesn’t realize its not normal for a mare to drain an entire bottle of tequila in an hour.

Here is another Crazy Headcanon. Celestia did not throw the fight with Chrysalis, nor did the stolen love super charge Chrysalis to the point of being stronger than Celestia. Celestia had to hold back most of her power in that short fight.
 
If she unleashed the full power of the sun in her magic she would have won with ease, but Canterlot would have been a burning ruin as a result due to collateral damage. If there was no chance of collateral damage in the fight, then Celestia would have won instantly.

@gasmaskangel  
Hey man, ponies don’t buy fancy outfits all that often, especially not in boonie-ass Ponyville. Factor in all that Element of Genorosity stuff, and Rarity needs to supplement her income somehow.

@Trickquestion  
I could totally see Rarity being a madame for a really classy brothel, or alternatively living a secret life as a high rolling card shark…
 
Idea for a fanfic: Ocean’s Eleven but with the main six and five background ponies, not sure who yet.
 
@Sjogre  
Oooo… an extension of that, poison joke when smoked is the pony equivalent of marijuana. Zecora is intimately familiar with it’s effects because she keeps a big crop of it in the back of her cottage. This is also why she speaks in rhyme all the time, its a side effect of her constantly handling the poison joke.

@gasmaskangel  
As far as she knows, the stuff that she’s selling is completely legal. While she’s technically supplying two different drug rings, she just thinks that there is a very large demand for extra potent energy pills, sleep aids, and pain relievers.
 
Well, okay, she knows that the spirit quest hallucinogens aren’t legal, but anything for a fellow witch doctor, right?
 
_{Note: She has no idea that Canterlot General University is a diploma mill and doesn’t even have a course in witch medicine.}

@gasmaskangel  
Yeah, that makes sense. It’s always been my Headcanon (which you might even call crazy) that Rarity has some illegal business on the side, which is how she livs her life of luxury. My money is on either gambling or prostitutes.

@Trickquestion  
No, its Zecora who’s the dealer. Why do you think she lives way the hell out in the Everfree Forest? So the guards don’t find her drug lab.

@gasmaskangel  
I always figured she just sold crack.

Rarity doesn’t actually make any money from Carousel Boutique, do to her habit of making dresses for free for anyone who looks like they need it, which to her mind is everyone of every species she sees.
 
The way she makes money is by extorting world governments as the international super criminal, diamond finger. Her elaborate underground base is hidden beneath the shop, with the primary entrance hidden in her inspiration room which is also why she doesn’t like anyone moving stuff in there.

@Sjogre  

 
Okay, I don’t have a crazy theory, but I do have a crazy idea for a story.
 
SCP-134 (http://www.scp-wiki.net/scp-134) is transported to Equestria (and turned into a young filly) who is then adopted by Princess Luna. No one is sure which universe the star systems in SCP-134’s eyes are from, but Luna feels a strange sort of connection to her, Luna herself being the alicorn of the stars (at least in her universe).
 
SCP crossovers are fun, but all anyone ever wants to write about is the world-destroying, mass-murdering, or mind-raping SCPs. That gets a little boring.

@Princess♠Molestia  
You call that a crazy theory? This is a crazy theory.
 
The Elements of Harmony are actually the enemies of all ponykind. Unfortunately, they have only a limited ability to disobey their wielders. Discord was trapped in stone as an alternative to killing or depowering him, Nightmare Moon was trapped in the moon to deprive ponykind of a powerful advocate, and then stripped of her anger and ambition when it became apparent that sealing her away wouldn’t work. They let Discord go free without argument or modification in hope that he would break the hold of the ponies before someone else took up the Elements. The Elements took the chance to switch around the lives of the manes in order to deprive Equestria of powerful agents, and failed to prevent Twilight from turning them back. They didn’t want to turn Twilight into a winged unicorn either, it’s just that her friends wouldn’t let them hurt her.
 
Heck, the only reason that they undid the damage Discord dealt was to deny the ponies the good reputation that cleaning up his mess themselves would have earned. That’s what secured the rule of Celestia and Luna, after all.
 
They ultimately hope for ponies to live in harmony with nature, instead of enslaving it. Instead, they’ve been enslaving nature and dominating most other species for most of their history.
 
_{One line about land whales. Really. Put some effort into it. Astound us. Confuse us. Confound us. Show us what kind of damage the drugs have done to your brain.}

All the bearers of the Elements of Harmony will become alicorns at some point in the future. Magic is just always the first. As it was with all the previous bearers.
 
 
Wait. That’s not crazy enough.
 
 
Equestria is really controlled by land walking whales.

Sombra spoke Latin in the past, that’s why he couldn’t speak English much.

@Soarin_the_Pegasus  
I’ll take it.

The Equestria Girls world is just an advanced computer simulation created by Celestia for her own amusement. Kinda like Second Life but with more virtual reality.

Shining Armor has the Holy Spear Longinus spell attack.

@Background Pony  
Maybe an illusionist may suit Luna as well.

@YetAnotherBrony  
Luna fits better as an assassin or an archer. And Celestia in Rage-Mode is an unstoppable berserker, considering in my headcanon that that the reason in Celestia’s “weakness” in magic is because she prefers to fight her enemies in melee.

@PonyPon  

 
“Blueblood is a pirate king” HAS to be true! Why else would he have a compass rose for a cutie mark?!
 
That sounds pretty funny actually. Though it’d probably only be beings from outside Equestria, since they’re, you know, the Princesses, and everypony knows them.
 
I wouldn’t think Celestia would want to style herself as a dragon-slayer. Luna, maybe, but Celestia has always been a bit more partial to subtler ways.

-Blueblood is secretly a pirate king.  
-in the days before NMM, Luna was mistaken for Celestia’s daughter embarrassingly often.  
-Celestia has a dragon-slaying reputation as legit as Oscar the Shark Slayer’s