When my SO and I first started dating, we began making a conscious effort to introduce each other to some of the movies that we loved or referenced quite frequently.
The following are 5 of the movies I had him watch with me:
[ol]
[li]Empire Records - I love quoting the lines (“Because that would hurt, Warren.” “Not on Rex Manning Day!” “SHOPLIFTER!”)[/li][li]Roadhouse - It’s so bad it’s awesome.[/li][li]Auntie Mame (Rosalind Russell version)[/li][li]White Christmas - It’s not Christmas if I can’t watch this.[/li][li]The Major and the Minor - I love me some Susu Applegate.[/li][/ol]
So here’s my challenge:
What 5 movies should a new SO of yours watch to better understand your obscure references or just you as a person?
Eek! I could never date you! 
Pretty tough limiting it to just five:
[ul]
[li]Any & all Monty Python (more quotes than others combined!)[/li][li]Dr Strangelove (nearly every line is quotable!)[/li][li]Office Space (modern day classic for anyone in IT)[/li][li]Neighbors (bit obscure but also classic)[/li][li]The Jerk (Steve Martin encapsulated)[/li][/ul]
The Godfather
The Hunt For Red October
Stripes
Batman (With Michael Keaton and Jack Nicholson)
Guys and Dolls
Chew on that for a while…muahahahahahahahha
L.A. Story - Steve Martin’s bizarre story about finding love in L.A. against all odds, with the help of a psychic highway conditions sign which is a reincarnated set of bagpipes. Really.
Unforgiven - most awesome western movie ever.
Monty Python’s Life of Brian - if you can’t laugh at religion, you can’t hang with me.
Monsters, Inc. - the story of a big hairy lummox and the little girl he loves. My life, basically.
King Kong, 1933 version. This one covers my love of both classic B&W movies, and my love of Giant Killer Something movies.
[quote=“melodyharmonius, post:1, topic:532873”]
[li]The Major and the Minor - I love me some Susu Applegate.[/li][/QUOTE]
Awesome! And after she cons the kid at the desk, he starts to sing Blues in the Night. She rocks.
Hm.
The Princess Bride (it’s just fairer than death, is all[1])
One of the Monty Python movies; really any of the three.
The Hudsucker Proxy - you know, for kids.
Lawrence of Arabia
A Fish Called Wanda (what was the middle one?)
[1] quote not actually found in the movie.
The Princess Bride
The Godfather
Star Wars, A New Hope
Star Trek II: Wrath of Khan
When Harry Met Sally
Not necessarily my top 5 faves, but if you like these we’ll get along just fine.
Yeah, that’s the point with mine.
If you can see the movies I listed and not think me too crazy - if you can understand why I find certain lines quotable, if you appreciate a little song-and-dance and different types of humor (punny and offbeat) then we’ll be fine.
My Cousin Vinny-so he’ll know what I’m talking about when I say “youts”
The Ring -I’m a huge fan of horror movies of the non-slasher variety
Sixteen Candles-“What’s happenin’, hot stuff?” is one of my favorite greetings
The Full Monty
The Good, the bad and the ugly
Capote
American Beauty
Big Lebowski
Do the Right Thing
Dead Man Walking
12 Angry Men
I picked six …
I could go a couple different ways with this, but I’m going to go with my list of recent (post-2000) movies that only I and people like me seem to ‘get’. With that in mind:
Josie and the Pussycats (“Jerkin! Tretorns are the new Adidas!”)
Ocean’s 12 (if you don’t think this is the best of the three, and if the Nightfox isn’t your favourite character, and if the Julia Roberts/Bruce Willis scene doesn’t make you cry from laughter…well, see ya later)
Domino (Keira Knightley and Mickey Rourke as a bounty hunter team, based on a true story!? “If you’re wondering what’s true and what isn’t, fuck off, because it’s none of your goddamn business!”)
Alexander (My favourite director telling the story of my personal hero – knowing all three versions (theatrical, director’s cut, and revisited) is essential as well)
Push (Bonus points if you fell asleep while watching it the first time but still recognised it as being the coolest movie from 2009 like I did)
Hard to limit it to 5 but these are the first ones that came to mind:
This is Spinal Tap
Being John Malkovich (which my wife hates BTW)
Oh Brother Where Art Thou?
Pee-Wee’s Big Adventure
The Jerk
Batman Begins
Office Space
Snatch
The Departed
Star Trek: First Contact
Citizen Kane
Singin’ in the Rain
Casablanca
Duck Soup
Pulp Fiction
Hmm…only 5, eh?
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Willy Wonka and the Chocolate Factory. This is my alltime favorite movie. If you don’t like it…well, I’m sorry for you. I don’t think we’ll get along very well. 
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Jurassic Park. I love quoting Ian Malcolm lines.
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The Manitou. Obscure, bad horror movie from the 70s, starring Tony Curtis as a sarcastic quack psychic pulled into a horrific situation involving a reborn (and very pissed) medicine man. I love it. I’m always quoting Curtis’s character’s lines.
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The Birdcage. Lots of funny quotable lines.
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Dogma. Ditto. Especially from the Metatron (can you tell I have a thing for sarcastic smart guys? Bonus if they’re British )
Honorable mentions: Fight Club, Harry Potter and the Sorcerer’s Stone, and *Back to the Future *(barely a day goes by when one or the other of us doesn’t say “He’s an idiot. Parents were probably idiots too.” )
*The Wizard of Oz *(There isn’t a character in this movie that doesn’t describe some part of me . . . yeah, even flying monkeys)
*Inherit the Wind
Lust for Life
The Fountainhead
What’s Opera, Doc?* (assuming cartoons are allowed)
Honorable mention: *All About Eve *or *What Ever Happened to Baby Jane? * (gotta have some Bette Davis in there)