To me this is the measure of a transcendent movie you absolutely love. The kind of movie where when you watch it again after a few years you're saying "Damn this is a good movie" to yourself. I promise to watch any movies that show up in this thread which I have not seen before, and report back.

Off the top of my head:

The first 3 Star Wars movies
Chronicles of Riddick
Boogie Nights
Airplane
Alien I and II
As Good as it Gets
Office Space
Braveheart
Swingers
The Unforgiven
Broadcast News
Die Hard
The Good the Bad & the Ugly
Road Warrior
Goodfellas
Smokey & the Bandit
Wall Street
Meet the Parents
The Electric Horseman

There are probably a few more that will come to me over time.

True grit
Silence of the lambs
Shawshank redemption

The Natural
Shawshank Redemption
A League of their Own
Titanic
The Quick and the Dead
Tombstone
Gone with the Wind
Airplane
Remember the Titans
Gladiator
21 Days
The Notebook
Aladdin
The Sandlot
310 to Yuma
Grand Turino
Mr Brooks

I have not seen Gran Torino! Will watch soon.

The old 3:10 to Yuma or the new one? Guessing the new one.

I don't want to think of my list, but I'm sure its more than 50 long. I used to be a chronic rewatcher, but not anymore.

I debated more than 3 times or more than twice. You can give your more than 3x list if you want.

Fabulous movie!!

Actually I liked both 3:10 to Yuma.

Watched them with my dad, which is probably why I have an affinity for it.

What inspired this thread is I'm watching Trainwreck for the second time right now. Great movie. I will probably watch it again in 5 years.

Yeah I watched The Good, the Bad and the Ugly, Jeremiah Johnson, Butch Cassidy and the Sundance Kid, and a bunch of other classic movies with my stepdad, which will always be among my favorites.

Of course we also watched Jokes My Folks Never Told Me, and 2069 a Sex Odyssey when I was like 11 and it probably exposed me to sex way too soon. We had early cable. It was a mixed blessing. They didn't realize back then not to show softcore porno at 3pm when kids are home from school but no parents around.

Oh yeah - also watched the Richard Pryor concert movies with my stepdad at a young age. Early cable grew me up way too fast. But holy cow was he hilarious.

American Beauty
American Gangster
Gladiator
The Professional

Not movies but I've watched the following series 3+ times:
The Office seasons 1-5
The Wire
Breaking Bad

Groundhog Day, The Godfather I and II, and an obscure Albert Brooks movie called Lost in America. Probably A Few Good Men on tv.

brazzers trailers

Lost in America is not obscure it's awesome! You lost the nest egg!

I think it's likely I've seen Defending Your Life 3x but I'm not sure so I didn't put it on the list.

Probably seen "Pulp Fiction" 40 times, or more if you count picking it up in the middle when it's on TV.

the prestige

I don't think a movie that you will always watch when you come across it on tv (like groundhog day) counts. OP said you've intentionally watched multiple times

Oh yeah a bunch more standards just came to me - Risky Business, Top Gun, Blade Runner, Robocop, Starship Troopers, Total Recall, Terminator I and II. Weird Science, Karate Kid, Rambo First Blood, Rocky, War Games, Saturday Night Fever.

As long as you watch it from the beginning, serendipitous viewing counts imo.

Good point movies I probably watch 3+ times on Skinemax:

Bilitis
Fiona
Lady Chatterly's lover
Emanuelle
Emanuelle in Bangkok
Emanuelle in Rio
Goodbye Emanuelle
Valley of the Dolls

dr strangelove
the aviator
12 monkeys
choke
pulp fiction
wolf of wall street
godfather 1 and 2
kill bill 1 and 2
inglorious basterds
the life aquatic with steve zissu
the darjeeling limited
the royal tenenbaums
spirited away
apocalypse now
fight club
the jerk

Terminator 2
Braveheart
Jaws
Predator
Scarface
Charlie and the chocolate factory
Leon
Bloodsport
Ace Ventura 1&2
Lord of the Rings....haha just joking.

The Wizard of Oz
Casablanca
How Green Was My Valley
The Good, the Bad and the Ugly
The Conversation
Pulp Fiction
Michael Clayton
The Dark Knight

For my money Pulp Fiction is the most rewatchable movie. The Dark Knight is close, but the third act loses its steam a little with all the Two Face stuff.

Se7en
Good Will Hunting
Usual Suspects
Godfather
Terminator

A clockwork orange, best film of all time to me

I don't think I have a single movie in this category

Hit it and quit it, baby.