Very personal list, but these are the movies I keep coming back to and have watched numerous times. In no particular rank/order: Casablanca, Fantastic Mr Fox, Goodfellas, Alien and Aliens, The Shining, LOTR Trilogy, The Dark Knight, Memento. I can think of a couple more but these are the most prominent.

All the really good ones

Honestly, I have too many to list, but I'll name some of my favorites from different genres: The Incredibles, Rat Race, Drag me to Hell, Sweeney Todd, Crank, The Nightmare Before Christmas, Mean Girls, Final Destination 3, Titanic, and so many more...

I have watched the The Lord of the Rings movies I think almost each month when I was in high school.

Terminator 2

Easy pick.

My top six most watched (not necessarily the most rewatchable), in no particular order, excluding Xmas movies:

Pulp Fiction
Snatch
Casino
Shrek
The Little Mermaid
The Wizard of Oz

If we put Xmas movies in the there, you'll get Home Alone and National Lampoon's Xmas Vacation in the top three probably.  The Santa Clause would probably make the top five as well.  

Pacific Rim
The Thing (1982)
John Wick
Spider-Man: Into the Spider-Verse
The Crow

So many great films that I've kinda forgotten about. Think I'm gonna compile a list from some of these and buy them on Google Play.

Yeah, I can torrent probably all of them and many I own physically but I want them legitimately. Probably gonna start with the Quentin Tarantino films. Maybe one or two per month. I love them all!

On top of my head, I’ve seen the dark knight many times, also a couple Tarantino films a few times each, can’t say much about the others

Star Wars
The Matrix (the first plus just the highway scene of Reloaded pretty much ha)
OT Star Wars
Moneyball
Goodfellas
Dumb and Dumber
Billy Madison
Happy Gilmore (into dumb 90s comedies quite a bit ha)
This is the End

to name a few..