• Month Python and the Holy Grail
• Young Frankenstein
• Seven Samurai
• LOTR Trilogy

I see a lot of LOTR fans here. Good crowd.

In steam of consciousness order:

• Young Frankenstein
• Princess Bride
• Double Indemnity
• Nightmare Before Christmas
• The Breakfast Club
• The Fifth Element
• 12 Monkeys
• The Terminator
• Star Wars (first trilogy)
• Harvey
• The Good, The Bad, and The Ugly
• Men In Black
• The Incredibles
• Inception
• E.T.
• The Sting
• Grease
• Ghostbusters
• West Side Story

Probably a number of others

I haven't seen it listed here in a quick scan, so:

Office Space

I revisit Eternal Sunshine of the Spotless Mind every few years when I wanna get my guts all twisted into knots.

I think when Kaufman is left on his own he's too much of a bummer and Gondry on his own is just too far out. But somehow they come together in a perfect balance with Jim Carey in perhaps his best serious role, IMHO. The soundtrack really takes it the extra mile.

I appreciate it because Joel and Clementine come off as just two kinda fucked up people having a kinda fucked up relationship; very relatable. Neither is perfect or completely at fault and the film very much leaves it up to your interpretation if they can or should work together. I don't think it has a happy ending, do you? Compare that to something like 500 Days of Summer where you're really supposed to sympathize with Joseph Gordon-Levitt's character but mostly I end up wanting to push him into the mud. Hard.

The subplot between the doctor and his secretary is maybe a little unnecessary? But Kirsten Dunst is amazing so whatever.

I wish I had stayed.

• Rocky Horror Picture Show (1975)
• The Good, The Bad and the Ugly (1966)
• Star Wars: A New Hope (1977)
• The Third Man (1949)
• The Ladykillers (1955)
• The Big Lebowski (1998)
• Repo Man (1984)
• Stalker (1979)

Probably several others, but those are the first to come to mind.

I don't re-watch movies very often, and more than three times is rare as hens' teeth. Sometimes it's because it's an absolute classic, or sometimes it's because I'm weirdly fascinated by it. Let's see if I can remember those rare exceptions.

• Starship Troopers (good movie, and something about it charmed my socks off)
• Les Triplettes de Belleville (absolutely must-see, smashing masterpiece, no need to know French) (free to watch here!)
• Big Lebowski (words cannot describe)
• The Life of Brian (Monty Python's finest movie IMO, and a fascinating commentary on religion)
• Fire and Ice (good movie, and I found the rotoscoping utterly entrancing) (free to watch here and here!)

I lost count:

The Marvel Cinematic Universe movies. I know it's popular to hate on them and point out flaws, but most of them are perfect "junk food" comfort food flicks. And some of them are really good!

I’ve probably seen Hot Fuzz more times than any other movie. It was a comfort movie for a while.

Pretty much any studio Ghibli movie. Have watched spirited away, Totoro, howls moving castle, valley of the wind, and many more more than 3x. Don't often rewatch stuff but have a soft spot for ghibli!

Princess Bride

A ton, but the one I'm most inclined to talk about is The Thing (1982). We rewatch it almost weekly since I introduced my spouse to it which is amazing because each time we spend about an hour afterwards dissecting the things motives, the order of replacements, different theories, etc. It's truely one of the best movies ever made. The practical effects get a ton of praise, but for me it's just gotta efficiently the movie is at what it does. You know every character within minutes of their appearance, you feel the alienation and paranoia, and the thing itself is so inexplicable that even after hundreds of watches in my life time I genuinely can't rationalize why it does what it does.

The 2011 one would have been better if they left in the pilot alien and had better set and custome guys. It doesn't feel like a pequal, it feels like a remake set in 2011.

Jurassic Park. (1,2 and 3)

Tremors (1 and 2)

Lake Placid (RIP Betty)

And Then There Were None

The Thing

Robin Hood (Disney animated version)

Star Wars (Original trilogy + Episode 1)

Addams Family Values

Django Unchained

Inglorious Basterds

Pulp Fiction (not a Tarantino stan, I swear)

Who Framed Roger Rabbit

Aliens

Raiders of the Lost Ark

Ironman (first one)

Pacific Rim

Girl with the Dragon Tattoo

The Big Short

Probably more than that TBH. I rewatch a lot.

Off the top of my head / all-time popular:

• Avatar (the blue alien one)
• Interstellar
• The Dark Knight trilogy
• Lord of the Rings trilogy

To satisfy my inner little boy:

• Ip Man
• Transformers
• Pacific Rim

Animation:

• Frozen
• How to train your dragon trilogy

Yeah I'm a basic bitch

These are just movies I've probably seen more than 3 times in no particular order, they aren't all necessarily masterpieces (though some are):

Everything, Everywhere, All at Once

Princess Bride

Blade Runner / Bladerunner 2049

Idiocracy

Interstellar

Spaceballs

Clue

The Other Guys

Dr Strangelove

Airplane! / Airplane 2!

Terminator 2

Kung Pow: Enter the Fist

Bill and Ted's Excellent Adventure

Home Alone

12 Monkeys

Inception

The Iron Giant

Trading Places

Star War: Backstroke of the West, The Third Gathering

All LOTR and Harry Potter movies

• Holy grail
• The only two terminator movies that have been made
• Akira
• Black cat white cat
• Underground
• Casablanca
• Cabaret
• Lotr
• Wall-e
• Totoro (and a bunch of other ghibli movies) 
• Pulp fiction
• Life aquatic (because I always forget the story and whether I like it or not) 
• Napoleon Dynamite (will never not recommend this to anyone, regardless of cultural snobery)

Probably a bunch more

The Fifth Element comes to my mind immediately. It was my happy place.

The Lord of the Rings, It's what I watch when I felt lost.

Also, Nostalgia, another film I rewatch when I felt not belonging and nowhere to go back to.

Hot Shots! Both, btw

Primer

Napoleon Dynamite

Unusual or less known movies I've watched a quite a few times:

• Leaves of Grass

• A Scanner Darkly

• Red Lights

• Where the Buffalo Roam

• Fear and Loathing in Las Vegas

-2010: The Year We Make Contract

My mind is blanking on the others

A subset ...

• Ghostbusters (1984)
• The Princess Bride
• Wrath of Khan
• Lord of the Rings
• Aliens
• The Bourne Identity
• Life of Brian
• Monty Python and the Holy Grail

My no-doubt incomplete list (I enjoy watching old favourites over):

• Bladerunner
• The Blues Brothers
• The Princess Bride
• Baby Driver
• The Cornetto Triliogy - Shaun of the Dead, Hot Fuzz, The World's End
• Monty Python - Holy Grail, Life of Brian, Meaning of Life
• Star Wars Trilogy (original and best)
• Dune (the David Lynch one)
• It's a Wonderful Life
• Twelve Angry Men
• Die Hard
• Alien
• Aliens

There are plenty (nearing my 60s, I've had plenty time to watch movies ;). So allow me to name just a few I always enjoy watching. They are in no order save the two first ones:

• '2001 A Space Odyssey'. There are movies, many are not that great, some are excellent and of those a few are true work of art, and then there is '2001'. I'm an admirer of most of Kubrick's work but this one is in a category of its own. I hated the first time I watched it, then I watched it again and was blown away, sequence after sequence. And I'm blown away every single time I re-watch it. It's one of the two movies I consider on par with the greatest books I've ever read.
• 'Les enfants du paradis' (Children of Paradise). Marcel Carné, 1945. A french movie and the second of the two movies I consider as good as the best books I've ever read. Maybe even more than 2001...
• '12 Angry Men'. Or what it means/should mean to live and to be a citizen in a democracy.
• Gone With the Wind.
• Ghost in the Shell (the original anime)
• The Dictator (Chaplin)
• 'The Life and Times of Judge Roy Bean'. I love this movie despite all its flaws. I love every bits of it, even its flaws. And I love its ending even more.
• 'Dances with Wolves'. I'm a sucker for Westerns and this one, right with 'Open Range' and maybe 'True Grit' (the Cohen version), which is also a great novel, is my all time most... loved Western. Not my favorite, but the one I love the most. Every time I watch it makes me wonder what the USA (and the rest of the world) could have been if they had managed to get rid of their hate (of the natives, and of nature). I should also list the Newman/Redford 'Butch Cassidy and the Sundance Kid'. But I feel bad for only listing so few as there are many more great Westerns and even a few truly amazing ones (there is also a lot of turds, I will admit it). This genre deserves a thread on its own as it so often overlooked or ignored because of its label. It's sad.
• 'Somewhere in Time'. next to Westerns, I'm a sucker for love stories. This one makes me cry every single time. I also like 'When Harry Met Sally', a lot.
• A History of Violence. I expected not much of it but it happened to be a great movie. With an amazing casting.
• The Birds (my favorite Hitchcock, so different from du Maurier's original short story which is also excellent, btw)
• North by Northwest (another Hitchcock, another of my favorites)
• Toy Story (the first 1, maybe the 2nd too), Ice Age (the 2 first ones)
• 'Singing in the Rain'. The movie I've watched the most, bar none?
• 'West Side Story'
• 'Scarface' (the one with Al Pacino).
• Kick Ass (the first one) made a huge impression on me. And gave me hope that all was not lost with contemporary US cinema that has grown afraid even of its own shadow and has started self-censoring, hard.
• A clockwork Orange.
• Full Metal Jacket (there is a lot I like less in it but it still is a great film)
• Barry Lyndon. God may have created light but Kubrick mastered it, in that movie.

There are so, so many more! Ozu is one of the directors I can endlessly watch and have a blast, I'm also a fan of Kurosawa. I have not even considered Italian (like, they were among the best) or the Russian cinema! Or even my own French movies: back in the days, French used to make a lot of great movies but that was before we too, like Hollywood, became so afraid of our own shadow that we started self-censoring... Sad times we're living in, bu that will pass.

Snatch

Young Frankenstein
Pulp Fiction
Big Lebowski
Airplane! with Zero Hour! (1957) immediately after
Fifth Element
The Death of Stalin

Big Trouble in Little China

Princess Bride

The Adventures of Baron Munchausen

Tank Girl

Romancing the Stone

Fear and Loathing in Las Vegas

Where the Buffalo Roam

Everything by Monty Python

Edit: everything by Mel Brooks

Lots.

The OG Star Wars (4, 5, 6)

Shawshank Redemption

Edge Of Tomorrow

Top Gun

Princess Bride (top 5 sword fight!)

Most all of Pixar’s stuff, and Dreamwork’s kids movies. My kids grew up with them.

Sleepy Hollow (Depp/Ricci version)

The Departed

Rob Roy (another top 5 sword fight)

Dune (original ‘80s version)

Alien/Aliens/Alien 3

Tron

Goonies

Rat Race

Lost Boys

Robin Hood: Men in Tights

The Breakfast Club

Ferris Buellers Day Off

Deadpool

The LOTR trilogy

Blade Runner - both films

Heist (a lesson in writing a script consisting of one-liners)

Ocean’s 11

The Name Of The Rose

The Last Mohican

Master And Commander

5th Element

Any of the Monty Python films, but especially Quest for the Holy Grail

That’s a start.

If I had to whittle it down to absolute favorites: Princess Bride, Monty Python, and OG Star Wars.

Idiocracy, numerous times.

As time passes, it gets worse (aka reality does. The movie is perfect)

I probably watched The Man from Earth (2007) over ten times.

Princess Bride

Strictly Ballroom

Paul

Close Encounters of the Third Kind

Star Wars 4,5,6

LOTR all of them

Operation Petticoat

Dr Strangelove

The Great Race

Pacific Rim

The Abyss

True Lies

Alien

Aliens

Clue

The Cutting Edge

Forbidden Planet

Harry Potter series

Kelly's Heroes

The Last Starfighter

Young Frankenstein

Raiders of the Lost Ark

The Rocky Horror Picture Show

Star Trek movies: Wrath of Khan, First Contact

Those Magnificent Men in Their Flying Machines

Gumball Rally

The Lord of the Rings - watched these many times now, and a couple of those have been back to back marathons. And yes, extended editions every time.

The Little Mermaid - The original Disney animated version. It’s possibly my favourite of what is known as the renaissance era.

The Muppet Christmas Carol - I watch this every year on Christmas Eve. I think I’m up to about 15 or more years now. It’s without a doubt the best version of A Christmas Carol ever.

Top three off the top of my head. I’m sure there’s more but the won’t match the number of times I’ve watched these.

Galaxy Quest

Far too many to name, so here's the first 10 that come to mind:

• Ghostbusters
• Star Wars
• Goodfellas
• Aliens
• Clue
• Back to the Future
• Twin Peaks: Fire Walk With Me
• Akira
• His Girl Friday
• Escape to Victory

I think in general comedies are just way easier to rewatch for what ever reason.

Also I think just because I rewatch a movie a lot does not mean it is the best movie. I think some movies just give a certain vibe that is enjoyable.

• Airplane
• Naked Gun
• Scary movie
• Simpsons movie
• Spirited Away
• Se7en
• The Prestige
• Inception
• Weathering with you

I probably also watched some Christmas movies a ton of times just because they played on TV a lot when I was a kid like Home Alone.

The Rocky Horror Picture Show

Hundreds of Beavers! It's an absolute delight showing it to someone who has never seen it before.

How to Train Your Dragon

used to fall asleep to it every night

• Mean Girls
• Inception
• Harry Potter series
• The Lord of the Rings Trilogy extended edition

i don't even have an answer for that. but i grew up pre-internet and owned lots of video tapes.

i'm marveling at the notion that there may be people who haven't rewatched movies a lot?

The Departed

Godfather 1 & 2

Rogue One

The Fifth Element

Dune 1 & 2

The Princess Bride

Star Wars 1-6

Anchorman

Big Fish