Crazy Headcanons

Scrounge
My Little Pony - 1992 Edition
Wallet After Summer Sale -
Not a Llama - Happy April Fools Day!
Since the Beginning  -

nobody's favorite
Queen Chrysalis would rather be feared than loved because she has the changeling equivalent of an eating disorder.
Phantom Rider
Solar Supporter - Fought against the New Lunar Republic rebellion on the side of the Solar Deity (April Fools 2023).

You are already booped.
Twilight Velvet and Night Light can’t have foals but it pays to be close to the Princess. The reason Starbutt and Shieldbutt are so OP: Tia magic’d them into existence from scratch, just making sure they looked like they could be the biological children of Velvet and Nighty. And she was actually holding back with their power levels when she did so.
Nyperold

Tickling Pony Bellies
@RhodieNite  
Well, Libman has said that one of the challenges of yelling as Fluttershy is not sounding like Pinkie. I wonder if it’s hard to talk in a soft and sweet voice as Pinkie without sounding like Fluttershy.
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]
When Starlight went back to Ponyville after the whole deal with the Princesses and stuff, Twilight was nowhere to be found. Searching high and low, she found out that Twilight had turned herself into a pickle.
 
SG: “… Why? Why would you do this? Why would anyone do this?”  
TS: “The only reason anyone would do this, if they could, which they can’t, is that because they could, which they can’t.”
user4897
Artist -
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.

Starlight and Sunburst spend a night at the latter’s house at Crystal Empire. Then the two shares some sad but lovely moments, including little flashback about Starlight’s past. Both feels sad upon remembering their respective shameful past. They realize their mistake and make amends once again, then proceed to warmly hug and sleep together
user4897
Artist -
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.

I’ve been thinking of this
 
My Little Pony: Friendship is Magic - All Grown Up
 
The story revolves in the future life of Mane 6 as adults, some of whom are already married and having foals. It’s set roughly 7-8 years after Season 7
 
Twilight is not yet married, but she’s now the new leader of Equestria alongside Cadance. Celestia and Luna looks more older, and has retired from royal duties. Despite this, she’s now in relationship with Flash.
 
Pinkie is married to Cheese and both are having a drastic change of personality, now becoming a mature sweet-talking couple rather than hyperactive party-loving ponies. The couple also build their own bakery next to Sugarcube and having two playful foals; one colt and one filly.
 
Rainbow Dash is married to Soarin’ and both are new leaders of the Wonderbolts.
 
Flurry Heart is now a 8-year-old filly and attends Ponyville Schoolhouse, having lots of friends
 
Spike has transformed into a deep-voiced stallion unicorn and is married to Rarity. They has yet to make foals, but Rarity still works at her boutique, which is now larger and more luxurious. Spike is now also a Royal Guard.
 
Fluttershy and Applejack are not yet married, but still working in their respective homeplaces. Big Mac in the other hand, already married Sugar Belle and now having a 1-year-old filly
 
CMCs and their Schoolhouse friends are in the same age as original Mane 6, but still maintain their clubhouse and help younger ponies like in the past
 
Starlight married Sunburst and having a 4-year-old unicorn filly who is a powerful magical prodigy, even able to do extreme spells like her mom did in Every Little Thing She Does.
 
Starlight’s old village is now built into a more modern town looking like Ponyville, with most of its inhabitants are now married including Sugar Belle.
 
The Pie Family now living in modern lifestyle in Ponyville, with the Maud, Limestone, and Marble now having a more “youthful” appearances with different hairstyles.
 
Granny Smith and Grand Pear survives, and the two lives peacefully in a new house somewhere in Ponyville.
 
There are now technology in Equestria, including mobile phones, automotive, computer, Internet, and much more
user4897
Artist -
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.

@RhodieNite
Honestly, this just sounds like a full-blown shipping theory. And also, Spike turns into a stallion and marries Rarity?
Not my cup of tea.
 
I know it’s kinda weird, sorry  
suddenly this headcanon pops up in my mind after seeing some shipping :P
hironakamura
Artist -

I have a theory that Rarity’s accent is fake. Her parents don’t talk like that. Her sister doesn’t talk like that. She’s like Dexter from Dexter’s Lab with an inexplicable accent.
Background Pony #2566
dunno it qualifies as Crazy or not but I see Spoiled Rich as Daimon’s STEPmother.
with her biologic mother being dead or insane.
@Shadow Star
Spoiled is Diamond’s biological mother, but sometimes Diamond pretends they’re not related as a coping mechanism.
 
Spoiled is Diamond’s biological mother, but Diamond herself was entirely unplanned. It’s actually the reason her mother dislikes her. Spoiled didn’t even really like Flithy Rich all that much… she was just dating him as a way to meet his richer contacts in Canterlot and had every intention of “trading up” and leaving town forever. The pregnancy ruined all that, and despite Filthy doing the honorable thing and marrying her, she still resents losing a possible palace lifestyle and having to stay in a Podunk town with a stallion she doesn’t love and a daughter she doesn’t want/actively neglects.
DanielTepesKraus
Greatest Poster in the Board -
GREEN - TALK TO ME
Roseluck - Had their OC in the 2023 Derpibooru Collab.
Elements of Harmony - Had an OC in the 2022 Community Collab
Twinkling Balloon - Took part in the 2021 community collab.
Friendship, Art, and Magic (2020) - Took part in the 2020 Community Collab
My Little Pony - 1992 Edition
Wallet After Summer Sale -
Friendship, Art, and Magic (2019) - Celebrated Derpibooru's seventh year anniversary with friends
Equality - Was more equal than the rest of the people during the event and did the only smart thing: wasn't there :^)

will return
celestia cast her alicornification spell on cadance’s womb after she saw how well the twilicorn merchandise was selling because she wanted to cash in even harder
 
then cadence and shiny named the kid after a horrible catastrophe in an attempt to hurt her market appeal out of revenge.
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]
Once Celestia and Luna retire (with Twilight taking their place), they went on a world tour and visited a variety of lands both in their world and the alternate universes.
 
Discord sometimes follows them.
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