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Old School is by far the #1 movie we watch the most together, then maybe Anchorman, and a far 3rd would be Good Will Hunting (I dunno why we randomly watch that one a lot!)
Not sure if my FH would want me sharing this, but we do enjoy Love Actually together. 
We really don't watch movies together. He likes scary movies - I hate them. I love romantic comedies - he can't stand them. So we watch sports. :)
We watch Just Friends all. the. time. And old Adam Sandler movies like Billy Madison, The Wedding Singer, and Happy Gilmore.
I think the movies we have watched the most together are Zoolander, Anchorman and any of the Jason Bourne movies. FWIW, Miss Penguin, for some reason, I feel like we've seen Good Will Hunting a bunch of times together. I'm not sure why, but it seems like whenver we see it on, we stop and watch it.
Oh, wow. I just realized that my fiance and I have never watched the same movie twice since we've been together. However, he has gotten me into horror/suspense movies and we go to see them if we find the previews interesting, though we're going to be doing our research a little bit more after last time. Also, and I hate to say this, he's gotten me into some of the early Adam Sandler movies, which is a miracle since I generally don't like Sandler at all.
I think that Stranger than Fiction will become one that we watch frequently, as well as Last Chance Harvey, which technically is one we've seen twice, once in theatres and once after we bought it. I will also include Roxanne in the mix and any horror movies that we've dubbed as favorites. And probably anything Tim Burton.
I would say the movie we watch together most often is Forgetting Sarah Marshall (my favorite of the Judd Apatow batch!).
hmm dont know if we have a favorite persay but we usually love watching comedys - most of the movies listed above applies to that!
He also really likes watching love, actually so thats nice, cause I love the musy girly movies!
The Notebook.....anyone who haven't seen this movie have got to watch it. It is so romantic.
we liked
Blood Diamonds
Cool Running
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Juno-We have watched it so many times. We went to see it at the movie theater on our 3rd date. Which was the best date ever! Long story short, that's when I started to fall for him and when we had our first kiss. So the movie takes us back to the turning point in our relationship.
I envy you ladies who have your guys so well-trained (or they're naturally romantic)! Love Actually and The Notebook! I love those movies, but my FI would probably rather have his toenails removed with a pair of pliers than watch romantic comedies.
We loved Forgetting Sarah Marshall (ok, it was a rom com, but had some guy humor in it). But I think we have watched Borat together - or parts of it - about a billion times. It may be "so 2006," but it still makes us laugh. Can't wait for the the new Bruno movie in July.
HARRY POTTER.
All of them.
Over and over again.
My husband doesn't usually like watching movies over and over again---whereas I do---but for HP he makes an exception. (@BubblyBride: he loves Nicolas Sparks stuff! And Jane Austen! I don't know what I did to get such a hopeless romantic for a husband.)
we love Just married (w/Ashton Kutcher and Brittany Murphy) and last week we bought Slumdog Millionaire and we've watched it like 4 times! we love it!
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We dont rewatch a lot of movies together but Anchorman, Wedding Crashers, Zoolander and judd apatow movies never get old for us lol
We don't watch a certain movie over and over. FI is just "appalled" (jokingly) that I haven't seen certain movies so we've been watching older movies (for example: Exorcist, Saving Private Ryan, and other random movies I haven't seen).
One movie we have seen a couple times is Pirates of the Caribbean 3 because it's one of my favorites (and the first few times we "watched" it, we ended up makeing out through the entire thing).
We don't really repeat movies, but the one that is most memorable that we've watched together is No Country for Old Men. We saw it in a theater the day it came out (which happened to be FI's birthday), and have watched it a couple of times at home because he has the DVD now. We've also both read the book, he before seeing the movie and I afterward.
"There Will Be Blood" and "Rushmore" are favorites from which we randomly quote lines to each other all the time.
This will sound wierd but the only movie we watch over and over is Transformers. We have been renovating our house for almost two years and for the first year we did not have cable. We rented a lot of movies but my FI had bought Transformers and since it was always there, we watched it over and over again!
Eternal Sunshine is definitely up there but we also like goofier movies and giggling at Paul Rudd or Will Ferrell hehe.
@chelseamorning: us too! Actually, I'm usually watching it and he joins me half way through so we can hang out together. :)
Hmm I have an extensive movie collection so I'd say the ones we've watched more than once together are Death At A Funeral, SuperBad, and Die Hard. Our FAVORITE to watch is definitely Milo and Otis!!!!
@ellebeaux - we LOVE Miyazaki movies too! Actually, I got my bf into anime and now he's just as obsessed as I am. Good men.
We love "Superbad".
We laugh like lunatics whenever we see McLovin and the two cops.
Anything funny or action-packed.
We love SuperBad and Knocked Up. Anything with Will Ferrell is a good bet too, especially Old School.
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The guy doesn't care for watching movies so we haven't watched many together - but I'd say Anchorman. It was the first movie we watched together plus we met in San Diego. And we both love a great comedy.
Some of ours have already been said, not surprisingly though: Superbad, Forgetting Sarah Marshall, National Treasure (we watch this all of the time for some reason), Home Alone (he loves that one, lol), Disturbia.
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I'd say ours is either Stepbrothers or The 40 Year Old Virgin.
What moveis do you watch together over and over?