I scrolled rather fast but one movie I didn’t see listed that I could watch over and over (and usually do if it’s on) :
Kill Bill Vol I & II
1776
***Once upon a Time in the West
Once upon a Time in America***
Nobody seems to have named any of mine…
Top Gun
Independence Day
Beerfest
OH… and Groundhog Day
These films I regularly watch over and over from my dvd collection (once upon a time they were videotapes):
Quatermass Xperiment/Creeping Unknown
X the Unknown
Beast from 20,000 Fathoms (I turn it off near the end cuz I absolutely HATE to watch the beast die)
House of Wax (1953 version. There is no other.)
Them!
The Maltese Falcon
The Big Sleep
To Have and to Have Not
Casablanca (the only allowed chik flik in my collection)
Destination: Tokyo
Rio Bravo
I have plenty of more modern films like Raiders and Mummy, etc., but the above are the ones I reach for first.
Star trek II: the Wrath of Khan.
Rocky (1,2,3,4), Rambo, Die hard, Enter the Dragon, Way of the Dragon, Bloodsport, John Wayne movies… all adrenaline 
After seeing some of the posts have to add Kill Bill, Indiana Jones, Star Wars.
Mostly kids films come to mind as being re-watchable:
Willy Wonka (original)
Spirited Away
The Incredibles
But also fight films e.g.
Drunken Master 2
We park our cars in the same garage! 
I saw Run Silent Run Deep listed at least twice and I saw someone else say they loved WW2 movies.
I’d like to suggest a Robert Mitchum movie called “The Enemy Below”.
It is one of my most favorite WW2 movies. I think it’s a much better submarine movie than Run Silent Run Deep - although many people would disagree.
I’m not exactly sure why it’s one of my favorites. It has a kind of sappy ending. But it just makes me wish I was there. If I had to serve in WW2, I would like to have served on that ship captained by Mitchum.
He was a great example of an officer who knew what he was doing and I find that very appealing.
Based on your list, I would recommend Across the Pacific.
It’s not a great movie. But I think you’d appreciate the stylistic elements. I know that I certainly do. I like to watch it at least once a year.
I saw one mention for Adventures of Robin Hood (Flynn);
Ordinary People - not a false note in the whole damn film;
The Mist - despite the ending;
The Green Mile - Jeez, I’m a Darabont junkie.
Already mentioned:
The Good, the Bad and the Ugly
The Godfather
My contribution:
Mulholland Drive
This. For me, the obvious choice, although it somehow slipped my mind in the above post.
Only two mentions of this film?
To Breaker Morant, I’ll add Gallipoli, Zulu, and King of Hearts.
My favorite WWII flicks include Decision before Dawn, 13 Rue Madeline, Orders to Kill, and The Train.
I’ve noticed a lot of people today don’t appreciate how groundbreaking a film it was. They see it, it’s a good story, but why all the fuss? they think. They don’t realize all the innovations in it that have become old hat today.
Maybe that’s it. Somebody once told me it seemed too dated. When I pressed for details, the only example offered was the newsreel voice-over heard toward the beginning of the film. I still don’t get it.
Anyway, it’s odd that more posters haven’t mentioned it. For years, it’s held a top position in those “film-critics’-100-favorite-films” kind of lists.
In particular, the “frame-within-a-frame” style of photography is what fascinates me.
I can always watch Fantastic Mr. Fox.
I’ve gone through phases where I watched the same movie over and over again - probably to an unhealthy extent. Probably the most pronounced of these was The Usual Suspects. I’ve also done it with The Thomas Crown Affair, along with *The Wolf Man *and some other Universal Classics.
You can never watch The Wolf Man too many times.