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Description

Car one

safe2289694 idw22669 applejack209254 fluttershy269626 pinkie pie267646 rainbow dash292166 rarity226858 twilight sparkle372695 alicorn338597 pony1719645 g42130569 car8924 exploitable meme33827 female1921505 mane 6 interests285 mane six39325 mare819459 meme97593 twilight sparkle (alicorn)155703
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Background Pony #7871
I thought Fluttershy would go with a Tesla. But I guess that wouldn’t be surprising enough.
Barry Tone
My Little Pony - 1992 Edition
An Artist Who Rocks - 100+ images under their artist tag
Artist -

Needs to know Hebrew.
I thought Fluttershy would’ve been into driving a Station Wagon with a trailer hitch. But, I’m a Wagon driver myself.
 
Pictured below is a 1991 Ford Country Squire. (Last year for that body style as far as Fords and Mercuries go, chronologically.) So many Wagons were smashed up in Demolition Derbies, but they were the SUVs and Minivans of the 1940s-1970s.
 
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Background Pony #ED0D
@YukoAsho  
A 1967 Cadillac El Dorado convertable–hot pink with whale-skin hubcaps and all-leather cow interior and big brown baby seal eyes for headlights.
Ferrotter
The End wasn't The End - Found a new home after the great exodus of 2012

I’m surprised Dash didn’t go for something faster, like a McLaren or a Bugatti. With Rarity’s answer, clearly nothing’s off the table.