If you could see....

well the thing is, you have to take your question seriously to get real answers.

What people will erroneously do, is list movies that they consider the "best" in terms of art, direction, writing, acting etc...

Which is all well and good, but at the end of the day, if you really had to watch a movie over and over again, it would have to be a movie with a high degree of watchability, and that's not always synonymous with the pinacle of cinematic achievement. Dense movies just don't have that some repeat value, even if they are very good.

So with that said, I am pretty sure I already know the answer: Back to the Future. I have literally seen that movie easily over ~70 times. (no exaggeration . I grew up with that movie, and every time it's on T.V. I can watch it and not be bored. I am NEVER fucking bored by that trilogy.
 
shawshank redemption might be up there too. I have watched that movie an assload of times as well.
 
Groundhog Day. I watched it over and over again on Groundhog Day which added a unique layer of redundancy and irony to the film.
 
Movies I've seen many times and still enjoy:

Monty Python and the Holy Grail
Shawshank Redemption
The Young Guns movies
The Life of Brian (Monty Python again)...
Natural Born Killers
Fight Club
 
The meaning of Life
300 (seen over 150 times already)
V for Vendetta
The Hunger Games
The Lord of The Rings Trilogy
The FIRST Star Wars Trilogy
 
Star Wars is certainly doable. Also, Dark Knight and Lord if the Rings trilogies.

Another favorite is The Quiet Man. Love that movie for some reason.
 
Groundhog Day. I watched it over and over again on Groundhog Day which added a unique layer of redundancy and irony to the film.
Dang....that was going to be my answer too. Yup.....Groundhog day! I watched it three times on Groundhog day.
 
Casablanca
The Original Star Wars Trilogy
Star Trek Movies
St Elmo's Fire
Love Actually

Those are the movies I've watched most, there are probably more though that I will think of later.
 
Casablanca
The Original Star Wars Trilogy
Star Trek Movies
St Elmo's Fire
Love Actually

Those are the movies I've watched most, there are probably more though that I will think of later.

Casablanca is one of my all-time favorites. I think that and The African Queen could be added to my list easily.

Love Actually is another very good movie. I've seen it a few times, and even used a clip to make a point to someone.
 
Casablanca is one of my all-time favorites. I think that and The African Queen could be added to my list easily.

Love Actually is another very good movie. I've seen it a few times, and even used a clip to make a point to someone.

I like the African Queen too. And The Misfits, one of my favorite movies. But I have seen Casablanca more than any other film. And I don't know what it is about Love Actually, but I love that movie! It always make me feel good. It's very funny too.
 
Also, I love how the sweet British guy in "Love Actually" is also Rick on Walking Dead. With some actors, you don't know how great they are until they do a few different roles.
 
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