Crazy Headcanons

Lord WyrmSpawN
Solar Supporter - Fought against the New Lunar Republic rebellion on the side of the Solar Deity (April Fools 2023).
Non-Fungible Trixie -
Thread Starter - MLP G5 Discussion and Speculation Thread
My Little Pony - 1992 Edition
Wallet After Summer Sale -
Friendship, Art, and Magic (2019) - Celebrated Derpibooru's seventh year anniversary with friends.
Friendship, Art, and Magic (2018) - Celebrated Derpibooru's six year anniversary with friends.
Not a Llama - Happy April Fools Day!
Friendship, Art, and Magic (2017) - Celebrated Derpibooru's five year anniversary with friends.
The End wasn't The End - Found a new home after the great exodus of 2012

Lingering Wyvern
It was common practice by unicorn royalty to arrange marriages between top archmages and heads of the military to produce an offspring of great magical talent and bodily strength.
 
Celestia herself arranged the marriage and union of the Velvet and Light families.
 
Twilight’s uncle would have received the honor of being teh groom were it not for his untimely death on the frontier.
Twi Clown
Silly Pony - Celebrated the 13th anniversary of MLP:FIM, and 40 years of MLP!
Shimmering Smile - Celebrated the 10th anniversary of Equestria Girls!
Solar Supporter - Fought against the New Lunar Republic rebellion on the side of the Solar Deity (April Fools 2023).
King Sombra - Celebrated the 10th anniversary of The Crystal Empire!
A Lovely Nightmare Night - Celebrated the 12th anniversary of MLP:FIM!
Princess of Love - Extra special version for those who participated in the Canterlot Wedding 10th anniversary event by contributing art.
Elements of Harmony - Had an OC in the 2022 Community Collab
Non-Fungible Trixie -
Kinship Through Differences - Celebrated the 11th anniversary of MLP:FIM!
Verified Pegasus - Show us your gorgeous wings!

Übermensch in training
Because of the changellings’ skills at shapeshifting, Thorax and Ember (and quite frankly any pairing with a changelling) is biologically plausible.
Lord WyrmSpawN
Solar Supporter - Fought against the New Lunar Republic rebellion on the side of the Solar Deity (April Fools 2023).
Non-Fungible Trixie -
Thread Starter - MLP G5 Discussion and Speculation Thread
My Little Pony - 1992 Edition
Wallet After Summer Sale -
Friendship, Art, and Magic (2019) - Celebrated Derpibooru's seventh year anniversary with friends.
Friendship, Art, and Magic (2018) - Celebrated Derpibooru's six year anniversary with friends.
Not a Llama - Happy April Fools Day!
Friendship, Art, and Magic (2017) - Celebrated Derpibooru's five year anniversary with friends.
The End wasn't The End - Found a new home after the great exodus of 2012

Lingering Wyvern
Aria used to be a kirin, Sonata a bat pony.
 
They made a magical pact with Adagio, the only natural siren among them, to become one of her race for power.
Scrounge
My Little Pony - 1992 Edition
Wallet After Summer Sale -
Not a Llama - Happy April Fools Day!
Since the Beginning  -

nobody's favorite
As soon as she heard Pinkie Pie talk about it, Silver Spoon’s goal has been to make Chancellor Puddinghead’s pudding recipe for herself. Pinkie’s shrugged it off, but Twilight is very worried.
Scrabbleman
Duck - He literally asked for this
Wallet After Summer Sale -
Friendship, Art, and Magic (2018) - Celebrated Derpibooru's six year anniversary with friends.
Artist -
Birthday Cake - Celebrated MLP's 7th birthday
Friendship, Art, and Magic (2017) - Celebrated Derpibooru's five year anniversary with friends.
The End wasn't The End - Found a new home after the great exodus of 2012

[screams in German]
Derpy can deliver mail anywhere. And I mean, anywhere.
 
In the middle of unchartered and dangerous territory, untouched for millenia? Derpy’s there.  
Fighting a deadly war with bits of poison berry pie flying all over the place? Derpy’s there.  
Currently trapped in Tartarus or the Moon for whatever reason? Derpy’s there.
 
The average populous may not trust her that much in delivering mail but the truth is, most government officials and spy networks send their mail through her. After all, it’s always a guarantee (so long as it’s marked important).
Random-Rambling
Solar Supporter - Fought against the New Lunar Republic rebellion on the side of the Solar Deity (April Fools 2023).
Non-Fungible Trixie -
My Little Pony - 1992 Edition
Wallet After Summer Sale -
Not a Llama - Happy April Fools Day!

tinyurl.com/dymbb3a
@Scrabbleman
 
It’s theorized that some ponies are gifted with tiny, tiny slivers of chaos. Discord himself is the largest shard of chaos, big enough to have developed true sapience, even maybe growing into a whole new chaos.
 
Ponies, being herd animals, are naturally attracted to order and hierarchy, thus their bodies of those chaos-touched have filtered its miniscule yet potent magic through their bodies so they can only be activated under certain conditions.
 
Pinkie can warp reality only if it would be “funny”.
 
Derpy can warp reality to deliver mail.
user4897
Friendship, Art, and Magic (2019) - Celebrated Derpibooru's seventh year anniversary with friends
Friendship, Art, and Magic (2018) - Celebrated Derpibooru's six year anniversary with friends.

In human age, Princess Celestia is only in her late 30s-early 40s, being born in the 1970s
 
Also in human age, Pinkie Pie is the youngest of the main cast (presumably born after 1999), which explains her flamboyant and happy, cheerful personality, while Starlight Glimmer is the oldest due to herself being used to be a cult leader
Background Pony #144A
Cozy Glow is actually a young mare trapped in a filly body thanks to Discord’s big prank eons ago. Also she and Discord used to be rivals of chaos to each other (and even became genuine friends) but due to corruption in power, Discord became more crueler and Cozy was no different when it comes to mischief and pranks and one day Cozy somehow was zapped into a filly during Discord’s rein of terror (probably as a result of her pissing him off at the wrong time). For years she had been planning on getting him back (and to restore her normal mare age) for the humiliation and with the help of Lord Tirek, she’ll stop at nothing to rule all over Equestria and to kill two birds with one stone by ridding them both.
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