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Champions of Equestria

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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
@ChangelingSR  
I would have assumed it was a Homestuck joke.
 
I am a big enough Homestuck nerd that I legit laugh at buckets.
 
Because Homestuck trolls use them in reproduction, therefore lewd.  
full  
Kinda like getting smacked upside the head with a dildo, but if you had to use one to make babies.
ChangelingSR
Artist -

Bucketling is bucketling because of a dumb joke wayyyy back when. Wonder twins reference from the Justice Friends I think. Form of, A Bucket of water!