Either Aliens with Rarity, or Tropic Thunder with Scootaloo. I honestly have no idea how Rarity would react, but my guess is that she’ll get super into it, and suspenseful huddles might ensue. I guess I got a death wish with my next choice, because the diabeetus from seeing Scootaloo rolling on the floor laughing would probably kill me.

Super Size Me with Applejack, and we laugh about how big he get’s in the movie, until she finds out that he’s eating meat, and I have to explain to her that humans do eat meat, and then she is like “You don’t eat meat, do you?” And I be like, “Sadly I do. But, unlike most humans, I prefer veggies over meat.” She then be like, “Well, at least you try to be more pony like.” Then I say “When in pony form, I hate the taste of meat. Human form, I do like meat, but not in pony form.” Then she be like “Good.” Then I tell her that the only apples McDonalds serve come in kids packs. She then say “I forbid you to eat there.” I would be like “I can live with that.”

Legally Blonde with Applejack….maybe she will appreciate the message of remaining true to who you are.  
Hey, if I have three favourite ponies, can I watch Legally Blonde with all of them? I think Rarity would appreciate the fashion driven character who is intelligent, yet creative and expressive. And Sunset Shimmer would probably not like the early oughties pop soundtrack, but would like the way Elle Woods is expected to fail by all her peers, and though she herself has to struggle through it each and every time, she ultimately stays true to who she is and teaches others there is nothing to lose by remaining true to yourself.

@Page Turner  
You wouldn’t be able to get her to stop singing “Everything is awesome” for weeks XD
 
@Background Pony #7CDA  
Celestia’s over a thousand years old. I’m sure she’s seen plenty of crap already. I imagine she might walk out, even, ‘cause I can’t imagine a soft, gentle version of Churchill, for example, enjoying a WWII movie like that.
 
@teslakana  
Fausticorn? Isn’t that just Lauren Faust, a real, married person, as a pony? :q
 
At least there wouldn’t be much in the way of culture shock or anything, heh…
 
@Vaidelot  
Fantasy epic? Dash? I think she’d love it.
 
…If she could get into it, that is. But seeing as she could with reading, I think she could here, too.

@Background Pony #D487  

 
That movie legit gave me PTSD.

Trippy.
 
Fear and Loathing in Las Vegas with Pinkie Pie.
 
Hopefully, her hedonism doesn’t level up from the experience.

Monty Python and the Holy Grail with Applejack. It would at least get a genuine laugh of out of her.

LotR trilogy with Dash. I’m sure she’d like it! Also probably she’d drink up half of my booze collection and passed out in the mid of the first film…

10 minutes into Netflix and Chill, and she looks at you like  

Oh god. Oh god, everything’s on fire! EVERYTHING’S ON FIRE!!

I’d be watching “Maverick” with Fluttershy.  
Apart from a few scenes, this should go over pretty well.

watching Gurren-Hen/Lagann-Hen with Celestia and/or Luna and/or Fausticorn.
 
This won’t end well…

I have a few favorites, actually, but I think Rarity would appreciate the creativity (and message) of the LEGO movie.
 
Barring that I could always show her one of my sister’s all time favorites, Disney’s Beauty and the Beast. Rarity seems like the type who would enjoy a movie like that.

@Manual_Monaro  
…Or maybe she plays The Ecstacy of Gold on her lyre. Or both!

I’m an indecisive little thing… It’s hard for me to pick a favourite anything.
 
But if I had to absolutely pick something, then I guess I’ll be settling down with Lyra to watch The Good, the Bad and the Ugly. I like to imagine she’d enjoy it, though perhaps finding it a bit slow-going in parts. Plus we’d cuddle the whole time.
 
Then a few days later she comes to me with her lyre and plays the theme song for me.

taken with the queen  
:) best night ever

Reservoir Dogs with Luna.  
I can’t even imagine what that would be like…

A Serbian Film with… wait. That won’t end well.

Watching an extremely violent movie, disney film, october sky, or secondhand lion with Fluttershy? Pretty well varies.

Fluttershy and I would spend the whole night telling each other “whatever you want to watch is fine.”

Saving Private Ryan with Celestia:  
It’d probably go a long way for explaining the duality of man: our ability to do good and our propensity for destruction.

It would be Forest Gump, and with Twilight…
 
Rage.jpg

I think Pinkie would dig the LEGO movie.

@Lillian  
really? A movie that JUST came out is your favorite movie EVER?