Jaws
Planes, Trains, & Automobiles

- A Christmas Story
- The Big Lebowski
- The Fifth Element
- Raising Arizona
- The Usual Suspects

I have probably watched Moon yearly since its release, too.

The Room

Chasing Amy
Shaun of the Dead
The Thing (1982)
Halloween (1978)

October: The Nightmare Before Christmas
December: A Christmas Story

I have a small BD collection of movies that I love and watch them over and over so no need to list them.

I do watch all 29 episodes of Twin Peaks every October. It is a tradition since first taping them off TV.

I don't know if I have any that I watch every year but on a pretty consistent basis my list is:

Back to the Future Trilogy
The Big Lebowski
Planes, Trains, and Automobiles
Terminator 2: Judgement Day

October:
The Exorcist
Let's Scare Jessica to Death
Messiah of Evil
Sole Survivor (1983)

Spring:
Valley Girl
The Breakfast Club

Summer:
Poltergeist
Prophecy (1979)

<----Her movies

My regular holiday schedule:

Early Summer

Summer Vacation


D-Day

Any WWII film

July 4th

Independence Day

September 11th

World Trade Center

Thanksgiving

Planes, Trains, Automobiles
Paul Blart Mall Cop

Christmas

Christmas Vacation
Christmas Story
Polar Express
Elf
Surviving Christmas
Four Christmases
Christmas With The Cranks
Sleepless In Seattle
While You Were Sleeping
Santa Clause
Trapped In Paradise

Christmas break time

Band Of Brothers

National Lampoon's Christmas Vacation
In December, obviously.

While there may be others I catch once a year, this is the only one I set out to do deliberately.

Bruce Lee movies
Firefly and Serenity
Pulp Fiction
The Wanderers
The Warriors

I don't watch any movies, even my favourite ones, on anywhere close to an annual basis. There's just to much else to watch/do.

The Paramount Theater in Austin has a summer movie series and Lawrence of Arabia is shown at the end of it, around Labor Day. It's been that way for the past 10 years at least.

Serenity
Shaun of the Dead
Batman Begins
Love, Actually

Wolf of Wall Street
Big Short
Scrooged
Santa Clause 2
Sorry to Bother You
There Will Be Blood
Spiderverse films (assume it’ll be the case with the 2nd)
The Muppet Movie


I could see Big Short falling off this list but feel confident I’ll continue to watch the rest at least once a year for the next decade or so.

Back To The Future
One of the Star Wars movies
Halloween
The Shining

Jaws
Die Hard
Back to the Future
Christmas Vacation
Reservoir Dogs

I feel like I used to watch a lot more movies over and over when I was in my 20s. Over the last 15 or 20 years my constant viewing of the same handful of movies has really gone down.

So many. At the top of my head:

"Close Encounters of the Third Kind"
"Alien"
"L.A. Confidential"
"The Last Picture Show"
"Donnie Darko"
"Leon: the Professional"
"Blade Runner"
"American Graffiti"
"Hedwig and the Angry Inch"
"The Exorcist"
"Goodfellas"
"Out of Africa"
"The Sting"
"The Grifters"

Me too. I chalk the reason for this being streaming and the Turner Classic Movie channel. Most of my viewing is catching up on stuff I've never seen before (pre-1990's movies, foreign films). Compared to 20 years ago, I have a wider selection instead of the same twenty or thirty DVDs over and over.

Have to? None
But most years I watch Die Hard and Bad Santa.

JAWS
Saving Private Ryan
Elf

Yeah most of these are because of my kids and the holidays, but we watch
Elf
Home Alone 1 and 2(and then they usually want to watch the rest but ugh)
Nightmare Before Christmas
My Neighbor Totoro
How the Grinch Stole Christmas (Darth Vader cartoon which I know isn't a movie and the Jim Carrey live action one)

and I try to sneak in Transformers the Movie (1986) for purely selfish reasons.

Memorial Day Weekend
Saving Private Ryan
Top Gun
Top Gun Maverick

July 4th
Independence Day

Holiday Season:
The Lord of the Rings Trilogy

My wife and I have watched Die Hard while wrapping Christmas presents on Christmas Eve for 15+ years.