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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
@BigMax  
Was that family guy, or was it simpsons?
 
Either way, from what I vaguely remember and can figure out just by looking at it and thinking, I assume its someone having some sort of violent drug hallucination, fighting it off by quickly getting drunk and summoning the pink elephant.
Masem
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
Friendship, Art, and Magic (2019) - Celebrated Derpibooru's seventh year anniversary with friends
Fine Arts - Two hundred uploads with a score of over a hundred (Safe/Suggestive)
Friendship, Art, and Magic (2018) - Celebrated Derpibooru's six year anniversary with friends.
Helpful Owl - Drew someone's OC for the 2018 Community Collab
A Really Hyper Artist - 500+ images under their artist tag
A Really Classy Artist - 250+ images under their artist tag
An Artist Who Rocks - 100+ images under their artist tag

@BigMax  
Actually, I’d expect pink elephants to be a possible species in Equestria.
 
It’s those pink hairless apes you have to worry about. :)