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ShutupIwasbored.

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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
Imperial/free agent for lyf. If they had executed Ulfric on the spot when they caught him, the civil war would be over. The dragon would still have attacked, you would still have gotten saved in the process and discovered you were Dragonborn and saved the day, but much faster without having to curbstomp racist douchebags in bear suits just so you can catch a dragon for all of five minutes before releasing it again.