Another entry for me would be "Robin Hood (1973)". I haven't rewatched it in a long time, but as kids we (my brother and me) wanted to watch that movie over and over again. I've seen it more than ten times at least.
Home Alone. It was one of my favorite movies as a kid.
I don't really rewatch movies anymore. There is so much content out there that I haven't watched, I would rather see something new than just rewatch something that I've already seen.
The Other Guys. At first glance, it's a buddy cop comedy that harkens back to Lethal Weapon, but with humor typical to ~2010. But, the more you watch it, the more Zucker brothers esque, 1980s surrealist comedy influences you notice. One of the most subtly weird and funny movies to me, I've probably seen it, no lie, 10 or 15 times.
I have a few that will be very close as I decided a bit over a decade ago to limit myself to one rewatch a year of each to stop myself sucking all the joy out of them:
Alien - my favorite survival horror
Aliens - my favorite Nam movie
Jaws - my favorite version of Moby Dick, although I really like Godzilla Minus One take on Jaws
Jurassic Park - best big stompy monster film for me
Lord of the Rings - this is always over Christmas. Its not faithful enough for me to the books but it still manages to be an outstanding Trilogy.
Not completely by my own choice, but I feel like I've seen National Lampoon's Christmas Vacation - at least in part - once or more per holiday season since it was released.
The same is true of Elf, but obviously that movie is quite a bit more recent.
For movies I've watched the most by my own choice, it's probably the Kill Bills or Inglorious Basterds, but those have got to be way behind in raw count. Goonies and the Back to the Future series probably have honorable mentions because of how long they've been around and continue to be a fun watch.
Kung Fury. It's a short film, so maybe that's cheating. Regardless, I love the writing. It's the perfect blend of absurdity and over the top action. It's a Swedish made film that's a satire of 80's cop and Kung fu movies. Free to watch on YouTube.
Seven/ Se7en
I know most of it's dialogue by heart. Went to see it at the theater when it premiered and stayed to watch it three more times, it blew my mind! I had never seen anything like it.
It is my favorite movie of all time.
There was a period of time in middle school where I was obsessed with Monty Python and the Holy Grail. Definitely not my favorite film anymore (not even my favorite Monty Python film), but since I don't really rewatch things nowadays it maintains its record.
Unless you count the one of the Disney movies my baby sister watched 3 times a day every day for months.
I used to fall asleep to John dies at the end for awhile so partial watches that wins hands down. But actually watching the whole movie probably lord of the rings or young Frankenstein.
It's the first movie I remember going to see (at a drive-in theater when I was 7). It was kind of a flop when it came out, but it's achieved a certain cult status for its surprisingly deep philosophy on fear, self-realization, and facing mortality.
I know it has to be Crouching Tiger, Hidden Dragon because it's the only movie I ever watched enough to literally wear out the tape when I only had it on VHS. There were times in high school I would just play it on repeat all day.
For a while, it was weirdly "Long Kiss Goodnight". It was getting heavy rotation on TV during my high-school exams, and improbaly watched it 15 times over the few weeks I was meant to be studying.
But now, probably LOTR extended edition, which I've seen every year since it came out, at my friend's annual birthday celebrations.
"Drei Haselnüsse für Aschenbrödel" (Three Hazelnuts for Cinderella). It runs at least a dozen times around each Christmas since I was a kid, and is part of the usual Christmas habits.
has to be old bud spencer and terrence hill movies, pretty popular in germany. I know there is a couple of them, but they are all pretty much the same anyway. ;-)
Thought it might be the Matrix, but then I remember that when my parents separated we only had one tape at my moms, Robocop, and no like movie channels. I was rewatching it like crazy.
Honestly it might be Finding Nemo. I think it was the first DVD we had and my younger sister was obsessed with it, so I'd watch it a lot with her. Things I'd watch at my own accord it's probably LOTR or Harry Potter though.
Honestly, it's probably Little Nicky for me. I do enjoy the movie myself, but back in my highschool days my main group of friends I would hang out and smoke weed with could always agree on this movie. If anyone would complain about what someone else wanted to watch too much, or none of us had a good idea for anything else, we would usually just throw Little Nicky on and be happy enough. I'll still watch every now and then even though I could recite the thing by rote.
Ben-Hur. Loved it in my youth, when TV still aired this kind of movies regularly, and I absolutely love it and like to review it from time to time. There are others I've watched again lots if times (Star Wars, The Matrix...) but Ben-Hur is number one.
I'm afraid they might be a whole bunch of oldies but goodies:
2001: A Space Odyssey. The Empire Strikes Back. Miller's Crossing (the third movie written and directed by the Coen brothers, from 1989). A Bridge Too Far (from 1977, a sprawling, star-studded epic about the Allies and their costly, ill-advised and ultimately unsuccessful Operation Market-Garden in WWII). A Bout De Soufflé. (Godard's seminal French New Wave cannon blast). From Russia With Love. The Spy Who Loved Me.
There's a dumb Italian Horror movie called Del Amore d'ella Muerte (Cemetary Man in English speaking territories) that I absolutely love. It was made in the 90s and stars Rupert Everrit as a graveyard keeper who fights a zombie invasion with his mute assistant.
Hard to explain but the universe they create is very comfy where he's drinking red wine and shooting zombies.
I’m not the kind of person who rewatches or rereads stuff. The only thing that I can rewatch endlessly is Pacific Rim. That movie is perfection for me. I even went to watch it on IMAX 3 times.