The Godfather 1 and 2.
Almost Famous
Lord of the Rings 1+2+3
Star Wars episode 4+5+6
I always enjoy watch O' Brother Where art Thou.
At the risk of sounding like a luntic ...
~300 times:
Star Wars ep IV
~200 times
Star Wars Ep V & VI,
Jaws
Raiders of the lost Ark
The Cannonball Run
~100 times
Where Eagles Dare
Battle Beyond the Stars
The Thing
~50 times
Magnum Force
Day of the Dead
Die Hard
The Terminator
Then there's the more recent movies, which tend to all be somewhere 10-20 times each like:
The Matrix
The Hills Have Eyes (remake)
Star Wars ep 1-3
But the list would be huge if I really thought about it. There are many, many films I have seen more than 5 times.
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Man in the Iron Mask
Conair
The Rock
Not my favorite, but was my kids'. "Jonah" (veggie tales)
The Lion King, The Matrix Reloaded, and Mighty Morphin' Power Rangers: The Movie. (the last show much of a nerd I am, but they don't call it nostalgia for nothing).
The Wall
Probably watched it five or six times in a few days before I really understood it
A few others that I remembered I have watched a lot are: Deliverance, Dances with Wolves, Braveheart, The Untouchables, The Manchurian Candidate (original), the Porkys movies esp. #1, The Searchers, Phantom of the Opera, and maybe a few more.
I like to watch new movies too and check them out, but I tend to watch some that I really like often. I watch more movies than I do TV.
O Brother Where Art Thou is my fave, probably seen that about a dozen times.
Dr Strangelove at least 50 times. Every scene is a classic vignette that stands on it's own.
I have quite a few:
1. All the Twilight movies
2. Gone With The Wind
3. Steel Magnolia's
4. Jerry McGuire
back to the future trilogy. love those movies. at one point i was watching them once a month.
the first is Zulu Love the movie
then " Lawrence of Arabia,
anything from Steven Segal,
Nicholas Cage,
Sean Connery
Not Really Sure.
I know I have watched all these a lot
Caddyshack
Animal House
Dirty Harry (including all sequels)
Planes, Trains and Automobiles
Stripes
A Christmas Carol (1951 version)
Elf
African Queen
Raiders of the Lost Ark
Goodfellas
The Godfather
Who really knows!
The life of Brian
One Flew Over The Cuckoo's Nest
The Exorcist
13th Warrior with Antonio Banderas. Love it!
Gladiator, Band of Brothers series, The Princess Bride (hilarious), Holy Grail, Boondock Saints. I could only have these movies and be just fine