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Daneasaur
Lunar Supporter - Helped forge New Lunar Republic's freedom in the face of the Solar Empire's oppressive tyrannical regime (April Fools 2023).
Perfect Pony Plot Provider - Uploader of 10+ images with 350 upvotes or more (Questionable/Explicit)

This conversation to me was basically Mac reaching out to the closest connection of a father figure he never had and wanting to talk to an older stallion who he could trust.
 
THAT snapped my heart in half.
Background Pony #3BD4
Then Mac became the next Ghost Rider and BO mentors him to control his powers and protect the innocent.
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
@RIG  
The general reaction of “I wanted to talk about your parents but I never knew when it would be a good time to bring it up” sealed it, Oak’s tone just cemented it.