When it comes to movies, the number I’ve watched more than five times is… embarrassingly large.
I grew up in the era of broadcast TV, VHS tapes, and cable reruns. If you loved a movie, you didn’t watch it once—you watched it over and over again until you could quote half the lines from memory.
Some of the movies on this list I’ve probably seen ten times. A few might be pushing twenty. And one or two may be somewhere north of that.
Here are the ones that immediately come to mind.
The Comedies
Some movies never stop being funny no matter how many times you watch them.
- Caddyshack
- Blazing Saddles
- Young Frankenstein
Mel Brooks alone probably accounts for several evenings of my life.
The Adventure Classics
These are the ones that defined a generation.
- Star Wars
- The Empire Strikes Back
- Return of the Jedi
And yes, I’m intentionally stopping at Episode VI. Episodes I–III? Let’s just say they’re not invited to the party.
The Guilty Pleasure
I don’t know why, but I’ve always loved this one.
- Real Genius
The Romantics
Every now and then a movie just hits the right emotional note.
- Top Gun
- Sleepless in Seattle
The Childhood Classic
This one probably started before I was old enough to remember.
- The Wizard of Oz
The Perfect Adventure
Few movies are as endlessly rewatchable.
- The Princess Bride
I never get tired of it.
My Personal Favorite
The original is absolute gold.
- Arthur
The Arthur remake with Russell Brand was cute, but rough around the edges. Dudley Moore nailed it.
The “Teacher Requirement”
When you teach certain subjects, some movies become annual viewing.
Because of my 8th grade class, I’ve seen To Kill a Mockingbird dozens of times. I show it every year, once with each class.
My journalism class has also added a few repeat viewings:
- Network
- All the President’s Men
- Shattered Glass
The Hitchcock Favorites
I’ve watched a lot of Alfred Hitchcock over the years, but a few stand above the rest.
- North by Northwest (even with the editing mistakes)
- Vertigo
- Rear Window
And honestly, Rear Window might be one of the greatest movies ever made.
The Christmas Traditions
Some movies simply belong to December.
- National Lampoon’s Christmas Vacation
- A Christmas Story
- Miracle on 34th Street
- White Christmas
And the best of all…
- It’s a Wonderful Life
My Favorite TV Series
As for television, one show stands above the rest.
- Moonlighting
I’ve watched the entire run multiple times. The writing, the chemistry between Bruce Willis and Cybill Shepherd, the humor—it was lightning in a bottle.
When I was younger, I shared more than a passing resemblance to a young Bruce Willis—at least that’s what people used to tell me. And if I’m being honest, I secretly wished I was a little more like David Addison: quick-witted, confident, and always ready with the perfect comeback.
Reality, of course, is less glamorous. But it’s still fun to revisit the version of cool that lived on that screen.
I’m sure if I sat here long enough I’d think of a few more. Movies have a funny way of sticking with us—sometimes because they’re great, sometimes because they remind us of a particular season of life.
Either way, if I’ve watched something five times or more, it means it’s become more than just entertainment.
It’s become an old friend.
Copyright © 2026 Doug DeBolt.
