The franchises of my youth: any of the original Star Wars Trilogy; Raiders of the Lost Ark; Star Trek II: Wrath of Khan; sure, let’s put Star Trek [Next Generation]: First Contact in here.
Not sure if I’m at five times yet for The Force Awakens, but must be getting close. All the nostalgia value of the original trilogy, with the bonus of far fewer cringe moments.
Franchise based on the favorite novel of my youth: Lord of the Rings, all three movies, extended editions. (Does not apply to Hobbit films.)
Godfather, Part 1 only.
Plenty of 80s & 90s action films that I saw well over five times back when I had cable in North America, and would still enjoy today: Predator, Aliens, Terminator 2. Who knows, maybe even Running Man, which I used to adore in a campy way but probably haven’t seen this millennium.
Pulp Fiction, probably? But haven’t seen it in a decade or so.
Pan’s Labyrinth. Like Godfather, I’ve taught it in “drama” courses, seen it again and again, and still enjoy it.
Blade Runner may rank as the film I’ve seen the most times - but sometime around the 20th viewing I stopped enjoying it.
Anything by Kubrick, the Coen brothers, Lynch and earlier James Cameron generally.
But to be more specific I’d say
Dr Strangelove
Fargo
No Country for Old Men
Oldboy (Korean version of course)
The original Terminator
The Matrix
Memento
The Big Lebowski
Seven Samurai
Back to the Future
Mulholland Drive
More will come to me after I post this, I’m sure. But the above movies are ones I can’t get tired of.
Big majority of movies I watched over 5 times were when I was a kid and had nothing else to do in the morning during holidays. The videotape era.
For instance:
The Godfather I and II
Star Wars 3, 4, 5, 6, 7, 9, R1
Lord of the Rings (especially 1, but all 3
Lord of the Rings (1978)
Shawshank Redemption
Alien
Blade Runner
A Few Good Men
Almost Famous
The Matrix
Gladiator
Back to the Future
Beauty and the Beast
Bill & Ted’s Excellent Adventure
Spaceballs
Billy Madison
Happy Gilmore
Black Sheep
The Karate Kid
Captain Underpants
Goodfellas
Rush: Beyond the Lighted Stage
Fanboys
Elf
A Christmas Story
Indiana Jones 1, 2, 3
Ghostbusters
Good Will Hunting
Sound of Music
Wizard of Oz
Mary Poppins
Old School
Rocky 4
The Lion King
Pulp Fiction
Star Trek 2, 5, 6, 7, 8
Toy Story 1, 3
Team America: World Police
South Park: Bigger…
Zoolander
Rudy
To Kill a Mockingbird