Not the slurs

But…what do you think ‘Derpy’ means? It’s from 4chan; what do you think it means?

@Scrounge  
Kinda hard not to love the derpy mailmare who’s always smiling

This doesn’t necessarily mean she has money. She might just have friends in high places.

@Frustration in Excelsis  
That’s because when you’re rich you can afford to keep the men in the white coats away

@Scrounge  
Or possibly Forrest Gump. Not sure.

If you’re poor, then you’re crazy; if you’re rich, then you’re eccentric.

@BRONY_USA  
Calm down with the caps lock

(darker voice) HOW DARE YOU CALLED DERPY A RETARD!!!!!

@Vree
 
My headcanon is now that Derpy is Equestria’s equivalent of Emperor Norton.

How does she get in to those posh events? Simple. Everypony loves Derpy.
 
A bouncer or attendant would see her and say “oh, if it isn’t Miss Derpy! (everypony knows Derpy) What a cute paperbag costume. You’re excited about your big night? Well, then it’d be rude to keep you up any further!” (stand aside while Derpy walks in happily pronking) “That does not apply to the rest of you, GET BACK IN LINE!”

Derpy to MLP is what Officer Jenny is to Pokemon.

My headcanon states that Derpy lives outside of Ponyville and doesn’t have to pay taxes.

The real retard is Snails.  
No, really. I think he actually might be developmentally disabled or something.

To me, she’s not so big on brains, but VERY big on heart.

Yeah…I’m gonna stick with my headcanon that she’s evil and only pretending to be stupid.

I see her as extremely intelligent with a wickedly fucked-up sense of humour.

Resisting the urge to tag all those background ponies…

 
This image now makes more sense.

@CottonTales  
Of course it’s fun to analyze the show. We wouldn’t have any fanon characters if people didn’t.

Here you go, Kanrabat  

@Mooncalf  
DAMN YOU!  
>headcanon’d.

She didn’t volunteer to pay for repairs because Applejack volunteered first (possibly as a PR move to boost Sweet Apple Acres publicity) and she didn’t want to insult AJ’s generosity. And she doesn’t want to flaunt her wealth in case ponies start treating her differently.
 
Of course, AJ eventually failed to pony up the promised cash, and yet the hall was repaired later. Obviously, SOMEPONY financed it…
 
My personal headcanon is that Derpy is an excentric trendcatcher who works with, among others, Fancypants of Canterlot to scout talents in art and fashion, such as Rarity, so they can promote them into fame and make good money by being first in on all trends. Fancypants work the Canterlot circuit, she handles Ponyville because she’s more rurally minded. Derpy’s carefully designed “well-meaning klutz” persona allows her to attend all sorts of events without raising suspicion, whether it’s a welcoming party for Princess Celestia’s number one student moving to town, snooping around Fluttershy’s coop to spot the latest pegasus pet trends, or just hang out in wells to catch some juicy gossip. And working as a mailmare is a great way to establish social networks.

@Daniel  
I’m personally just chalking that up to Canon Discontinuity, it stopped being a problem because it was no longer relevant, but it’s no fun to analyze it that way I guess