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Description

As per comments and twitter confirmations:
 
AJ is “The Man with no Name” (aka Clint Eastwood’s spaghetti western character)  
RD is The Lone Ranger  
Twilight is Marty McFly in Doc Brown’s “western” outfit from the start of Back to the Future 3.  
Rarity is Jessie from Toy Story 2+3  
Pinkie is Quick Drawn McGraw  
Fluttershy is Dale Evans (co-star of many Roy Rogers western pics)

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Comments

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Ardashir
My Little Pony - 1992 Edition

Fluttershy as Dale Evans? Pity she couldn’t have been Sally Starr (now to see if anyone gets that name).
 
And her as Dale Evans? Then I wonder what became of Trigger.
Scrounge
My Little Pony - 1992 Edition
Wallet After Summer Sale -
Not a Llama - Happy April Fools Day!
Since the Beginning  -

nobody's favorite
@ExOttoyuhr  
Yeah, I’m kind of surprised about that myself.
 
But who would she dress up as? Hmm… I know it’s a little outside the box, but how about Mal Reynolds? (Read: Yeah, I got nothin’.)
ExOttoyuhr

@Scrounge  
Amazingly enough, we don’t have any yet.
 
And yet, Sunset Shimmer already has a Western-sounding name and wears cowgirl boots; you’d think that the next step would be a natural one…