Obviously influenced by the corresponding thread by UnderwaterFunktown for games, made me wonder about the same when it comes to film.

I enjoy rewatching movies, but there are those where it doesn't matter how many times I've watched them, I never get tired of them. My 5 would have to be:

1) Galaxy Quest (A fun satire on the likes of Star Trek films, it blends the perfect combination of action and comedy with a perfectly cast Tim Allen)
2) Ocean's Eleven (I love a good heist film and Soderbergh's remake oozes style with both the aesthetic and music of the film that's timeless)
3) The Matrix (What's there to say? Sci-Fi masterpiece with a thought-provoking narrative, awesome action, and even cooler music)
4) Office Space (Probably my favorite comedy film. Memes galore and beyond quotable. Never get tired of this film)
5) Hard Boiled (My favorite action film of all time by the master himself, John Woo! To this day it amazes me how he managed to film these kinds of action sequences)

I'd never watch anything again

Probably something like this

Die Hard (my favourite film ever)
Jaws (considered a classic for a reason)
An American Werewolf in London (balances horror and comedy perfectly)
Austin Powers: International Man of Mystery (my favourite comedy)
Robocop (original 1987 version of course, it's just awesome)

If trilogies count as one movie, then it would be Star Wars OG trilogy (the original versions), the extended cuts of the LOTR trilogy, E.T., the Indiana Jones trilogy and The Wizard of Oz.

If trilogies don't count as one movie, I can't make a list. lol

LOTR extended versions and 2 out of 3 from Robocop, Total Recall and Starship Troopers.

Once Upon a Time in the West (best movie ever)
Kill Bill: The Whole Bloody Affair (I haven't actually seen it, but judging by vol 1&2, I want them)
Princess Mononoke (have to have one animation and while other Ghibli films like Totoro are arguably better, Mononoke is most rewatchable)
Monty Python's Meaning of Life (have to choose some comedy; this for variety and musical numbers)

For last one there are many tempting options: Blade Runner, A Clockwork Orange, Deadpool, Hellboy II, Dark Crystal, Das Boot, Godfather... But I guess I have to take one Finnish movie and that'll be dark comedy crime film Raid (based on books and sequel to best ever Finnish TV series).

I have them all bought on YouTube. When Harry Met Sally, Forest Gump, Groundog day (ironically) True Romance and Legends of the Fall.

I like the Harry Potter movies... I'm fucked.

Soo easy.
Tlotr trilogie.
Blade
Hellraiser 4

The Lion King (1994)
The fifth Element
The Greatest Showman
The Prestige
Amélie
Starship troopers

Shit, that is 6 movies. I need to cheat. Will not drop an of them.