5 Movies

The Cowboys
Lonesome Dove
Sicario
There Will Be Blood
No Country for Old Men

Bonus: Shawshank anytime it's on TV.
 
Just remembered, this I've probably watched 10x times (and I should track it down again to show my kids).

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I never have watched a movie five times... but I believe I may have seen Last of the Mohicans, Dances with Wolves, The Outlaw Jose Wales and Christmas Vacation four times.
 
Many Kaiju movies - Original Japanese Godzilla (not the one with Raymond Burr though that one too)
Episodes 4,5 and 6 of Star Wars
A Christmas Story - "You'll shoot your eyes out!"
Many of the Marvel Studios films
SpaceBalls, Young Frankenstein, Silent Movie, etc... aka anything Mel Brooks

Yeah more than 5
 
The Outlaw Josey Wales (pretty sure I could quote the whole movie word for word)
Galaxy Quest
The Empire Strikes Back
Hot Fuzz
Conan the Barbarian

(Honorable Mention)
Ride with the Devil
Drop Dead Gorgeous
Ronin
 
Just to keep it going...

Fight Club

Dirty Dancing (sooo many nights w/MS Robbie, stepping on each others feet trying to emulate, Never got it right, but I got to hold an Awesome lady close and laugh our night away)

Two Night Stand

The Patriot

Ghost Rider
 
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