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artist needed31130 safe2260073 applejack207495 fluttershy268342 pinkie pie265228 rainbow dash289727 rarity225215 spike94955 starlight glimmer62436 twilight sparkle370219 alicorn334326 pony1691618 g42120466 my little pony: friendship is magic266975 the cutie re-mark3595 bad end2936 chara175 discovery family logo12660 female1900565 friends are always there for you94 mane six38798 mare800223 spoilers for another series1808 twilight sparkle (alicorn)154492 undertale2128

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Background Pony #973C
There’s still one more left…
 
She’s gone now.
 
Sribbles a cross on Starlight Glimmer’s face in the photo
 
And done! Man, that was fun!
 
Now onto the next world!
hombad26
The End wasn't The End - Found a new home after the great exodus of 2012

Jokester, aware of the fourth wall, frequently violates space-time and physics, cares a whole lot about their sibling, and (according to fanon) harbors a secret dangerous side.
None of the characters are perfect fits, of course. He’s also got Dash’s laziness (and then some) and none of Pinkie’s siblings fit Papyrus’ personality at all.
 
Twilight is also a candidate for Sans, since Sans has a background in science. Also, as the most recent episode has shown, Twilight was really sad while showing Starlight the results of her actions, so if that kept up for a long time, she could easily become as depressed as Sans. Also her brother is captain of the royal guard, so I guess just de-age him a bit to when he’s still a recruit or something.
Minus
Nightmare in the Moon - Had their OC in the 2024 Derpibooru Collab.
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.
Non-Fungible Trixie -
Kinship Through Differences - Celebrated the 11th anniversary of MLP:FIM!
Philomena - For helping others attend the 2021 community collab
Twinkling Balloon - Took part in the 2021 community collab.
My Little Pony - 1992 Edition
Friendship, Art, and Magic (2020) - Took part in the 2020 Community Collab

Leader of the G4 purists
@skylinevs22  
It’s not gay, it’s bi.
 
But I feel like it was more about having a complete disregard for gender, focusing instead on the characters themselves. In any universes where one or several characters were the opposite gender, nothing would be different. Personalities and relationships would remain unaltered I am sure.
Wesley Foxx
Friendship, Art, and Magic (2018) - Celebrated Derpibooru's six year anniversary with friends.
Helpful Owl - Drew someone's OC for the 2018 Community Collab
Birthday Cake - Celebrated MLP's 7th birthday
Not a Llama - Happy April Fools Day!
Best Artist - Providing quality, Derpibooru-exclusive artwork
Friendship, Art, and Magic (2017) - Celebrated Derpibooru's five year anniversary with friends.
Happy Derpy! - For Patreon supporters
An Artist Who Rocks - 100+ images under their artist tag
Artist -
The End wasn't The End - Found a new home after the great exodus of 2012

The Fluffiest
@Background Pony #9FD2  
Pinkie.
 
Jokester, aware of the fourth wall, frequently violates space-time and physics, cares a whole lot about their sibling, and (according to fanon) harbors a secret dangerous side.
 
None of the characters are perfect fits, of course. He’s also got Dash’s laziness (and then some) and none of Pinkie’s siblings fit Papyrus’ personality at all.