What are some movies worth watching multiple times

The Matrix
Lord of the Rings
Dune
Blade Runner
Longest Day
Stalag 17
It's A Wonderful World
Look Who's Talking
Ghostbusters I & II
Batman Begins
Practical Magic
Jurassic Park
Matilda
The Great Dictator
The French Connection

Mad Max Fury Road
The Hateful 8
Pulp Fiction
No Country for Old Men
Forrest Gump
Flight of Dragons
Toys
Fight Club
Finding Nemo
Finding Dory
Moana
Encanto
The Hobbit (animated Rank and Bass)
Steel Magnolias
Parenthood
Hocus Pocus
The African Queen
Zombieland
Aliens

I could probably go on but I'll stop now.

King Kong, Casablanca, The Seven Year Itch, West Side Story, 101 Dalmatians, A Hard Days Night, Help!, Fantastic Voyage, On Her Majesty's Secret Service, Tommy, Up In Smoke, The Blues Brothers, Star Wars: The Empire Strikes Back, Raiders of the Lost Ark, Clash of the Titans, Pink Floyd: The Wall, Poltergeist, First Blood, Blade Runner, Flashdance, Footloose, Ghostbusters, Gremlins, The Breakfast Club, Back To The Future, Labyrinth, Spaceballs, Robocop, The Untouchables, Who Framed Roger Rabbit, UHF, Roadhouse, Batman, Home Alone, Wayne's World, Jurassic Park, Speed, Pulp Fiction, Hackers, Titanic, And Idle Hands.

Fight Club

anything by Quentin Tarantino

The Matrix, as someone else has also said.

Princess Bride, Dirty Rottten Scoundrels, Secondhand Lions , Indiana Jones ( the 3rd one )

Tombstone and Gladiator but I think the cat is out of the bag on those two.

Stripes with Bill Murray
Full Metal Jacket (1st half)
Captain America Winter Soldier

Modern Times (Chaplin)
Way out West (Laurel & Hardy)
Casablanca
La Dulce Vida (Italian)
Last Year at Marienbad (French)
Spirit of the Beehive (Spanish)
Humanoids from the Deep
Plan 9 from Outer Space
Voyage to the Planet of Prehistoric Women

Anything Orson Wells has directed or acted.

Godfather 1 & 2
Chariots of Fire
Crash
Legends of The Fall
The Pelican Brief
The Mighty Quinn
Good Will Hunting
12 Angry Men

Yes - Dasboot - the best film about the Uboat war in WW2🙂

Pirate Radio. It is about how in the early 60s British rock and roll radio stations had to start broadcasting on ships anchored in International waters off the cost of England because England banned stations from playing rock and roll. Cheers!

The Fisher king
Lions for lambs
The pursuit of happiness
Grand canyon
The lovely bones
Fearless (Jeff Bridges and Rosie Perez)
Roseannas grave (For Roseanna in U.S.)
Seeking a friend for the end of the world

For me, and I try and watch two: The Lion in Winter. I watch it on Christmas Eve.
The other movie is The April Fools. I try and see that on April first. Both movies if not mistaken are from 1968.

Free Guy
Iron Man
Avengers Infinity War
Lord of the Rings
The Holiday
Blast From the Past
O' Brother Where Art Thou
Rocky
Anything from Girlsway 😏

In the Heat of the Night.

12 Angry Men.

Inherit the Wind.

Bad Day At Black Rock.

Guess Who's Coming To Dinner.

They Will Never Forget.

Intruder in tbe Dust.

Shawshank Redemption
Bull Durham
Animal House
Amadeus
St Elmo’s Fire

Interstellar
Annihilation
Lucy
The Lord of the rings
The Hobbit

All the movies based on Jane Austin novels.

All the marvel movies and fast and furious series

The Green Mile
The Shawshank Redemption
Batman Trilogy (Christopher Nolan)
The Prestige
Forrest Gump
Sleepers

Hard Boiled

Because body count.

The Big Lebowski

the Commitments..

Gladiator

Rushmore

Baby Driver

Harry Potter

Goodfellas
Indiana Jones
Grease
Alien
The Good, the Bad and the Ugly.
Magnificent Seven
Mrs Doubtfire
Rear Window

Caddyshack, Vacation, for starters.

Depends on what genre you enjoy

Most of the recommendations here are awesome.

I'll add:

Shaun of the Dead
Hot Fuzz

Lot of them if you wait some years between watching. It almost becomes fun just to see where your memory sticks and falters