Subjects of Equestria! We are pleased to kick off the Nightmare Night Festivities and the 14th anniversary of the return of our beloved Princess Luna! Join us in celebration!
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Background Pony #8155
@SeraphimDawn  
If Cheerilee asked you to get her a glass of water, she’d probably name you “Princess of Hydration” during the time it took you to get it and come back.
Background Pony #8155
@Flutterfan  
@SeraphimDawn
 
Technically there’s three, going on the animations alone, and in no particular order:
 
•Rarity, “this year’s Rainbow Princess,” or in other words, the one who brings in the last color for the first rainbow of the season.  
•Lily Lightly, put in charge of the decorations for the Night of a Thousand Lights, and so named “Princess of all that twinkles and glows.”  
•Back in good ol’ Ponyville, there’s Wysteria She found Spike and the flower he kept, making her a princess according to him. In order to get her normal life back, she coronated everybody so they’d be equals again. So technically technically, they’re all princesses - yes, even Spike. Princess Spike has been a thing for a long time! But that never comes up again.
 
It’s funny, the three who are most clearly in charge of a lot don’t have titles at all, except for Ponyville’s Mayor Flitter Flutter. You get called a princess if you find a flower or put up lights real good, but Cheerilee and Star Catcher are just Cheerilee and Star Catcher. (Though my headcanon is, they try and try to give Star Catcher a title but she says she doesn’t need one; they follow her because they trust her, and if she weren’t worthy of that, a title wouldn’t help.)
Flutterfan

@SeraphimDawn  
2003: Celebration (Charming Birthday)  
2004: Friendship Ball (Dancing in the Clouds)  
2005: Butterfly Island (Friends are Never Far Away and A Very Minty Christmas)  
2006: Crystal Princess (Princess Promenade and Runaway Rainbow)  
2007: More Crystal Princess and 25th anniversary ( A Very Pony Place)
 
Is inconsistency a bad thing? Also, G3 had books of which I own seven of them.
Flutterfan

I don’t see Unicorn Cheerilee and Earth Pony Cheerilee as the same pony. Besides, Earth Pony Cheerilee is actually based off Cherry Blossom. Unicorn Cheerilee is a princess of unicorns.