Shawshank is on now.
I always end up watching A Few Good Men, Terminator 1 and 2, Shawshank, Apollo 13, DieHard (first 2 and usually 3rd) and You’ve Got Mail if they are on when I am flipping channels.
To Have and Have Not
actually any movie with Lauren Becall and/or Humphrey Bogart
I’d add Serenity, but really to me it’s not a movie, it’s the rest of the TV show that should have been. I could definitely watch Firefly again.
Shawshank Redemption
Sleepless in Seattle
You’ve Got Mail
Love Actually
The Green Mile
Apollo 13
Castaway
Forrest Gump
Pride and Prejudice (Colin Firth and Keira Knightly versions)
Out of Sight
Oceans 11 (George Clooney version)
Legends of the Fall
The River Runs through it
Princess Bride
The Hunt for Red October
GIgi
Sound of Music
Evils
To name a few favorites
During the holidays we love A Christmas Story and It’s a Wonderful Life.
The kids have all the Star Wars, Harry Potter, and Indiana Jones movies and love watching those on long trips.
When I was younger I used to watch all the Shirley Temple movies shown on Saturday mornings, and grew up on classics with Jimmy Stewart, Cary Grant, and Katharine Hepburn. DH loves Casablanca. I love All About Eve.
When people mention The Parent Trap, they do mean the original with Hayley Mills, right? I wanted to BE her when I was little! Besides Parent Trap, I also loved watching The Moonspinners and Pollyanna.
I actually like the Lindsay Lohan version of Parent Trap. She was a good little actor before she went off the deep end.
When Harry Met Sally
Joy Luck Club
October Sky
A Christmas Story
The Family Stone
Love Actually
The Exorcist ( only horror movie I have ever liked )
The Godfather ( except the 3rd )
Desperately Seeking Susan
Working Girl
The sound of Music
The Big Chill
Under the Tuscan Sun
Soul Food
Heartburn
The Deer Hunter
Goodfellas
Dead Calm
Cold Mountain
Good Will Hunting
Boys in the Hood
In the bedroom ( never seemed to make it as a hit , but what a film ! )
My Big Fat Greek Wedding
What can I say, I like to be entertained and amused. sometimes by sappy movies I can recite verbatim
I love October Sky too, lje62. The book that it’s based on, Rocket Boys, is great as well.
The Sound of Music
When Harry Met Sally
You’ve Got Mail
Bull Durham
Legally Blonde
Housesitter
Whoa. I see these big lists, and I wonder if you’re posting favorite movies or, as the OP asked, movies you repeat a lot.
Of course, with little kids, it’s different.
I’ve watched The Graduate more times than I can remember. It’s one of the first movies I rented with my first VCR back in 1986. Also
Alien
Aliens
Terminator
Terminator 2
The “good” Star Trek movies, esp Khan
Hitchcock, anything
30s screwball comedies
Casablanca, To Have and Have Not, Key Largo
The Seventh Seal
Blow-Up
If (why is Malcolm McDowell not a thing?)
2001 - but only if I’m in a special mood
Apocalypse Now - also not everyday fair
Donnie Darko - I spent a weekend getting drunk and studying that one, at age 48 or thereabouts, really absorbed - also the different cuts make a serious difference
American Beauty
Sean Connery as James Bond - all
A Hard Day’s Night and Help
Someone mentioned Bedazzled! So good!
Monty Python and the holy grail
MASH - the original
Excalibur! Best Arthurian movie ever
I love many old movies. I’ve seen Cary Grant, Doris Day, Rock Hudson, Myrna Loy, and Irene Dunn movies a gazillion times.
I also like many Tom Hanks, Meg Ryan, Sandra Bullock, Hugh Grant, Renee Zellweger, Colin Firth, and Reese Witherspoon movies and watch them over and over.
Parent Trap (both) and other Hayley Mills movies.
I’ve watched the BBC version of Pride and Predudice at least 20 times.
“I’m astonished that I’m only the second person here to mention Lord of the Rings.”
I heard that a while ago there was a short version of the trilogy circulating on the web. Someone took out the lion’s share of the endless battle scenes etc., and merged the rest into one movie, which was apparently quite good. Illegal, but good. 
Ok. Here are the animated movies that the parents in this household enjoyed watching over and over:
Up!
The Incredibles
All Toy Stories
The Lion King
Princess Mononoke
Spirited Away
The Iron Giant
Inside Out
Cars
Lilo and Stitch
The Triplets of Belleville
The Last Unicorn
agree with so many here! this makes me smile.
two of my favorites besides many mentioned above are The Fugitive and Elf.
(shawshank is also a favorite; i always felt like it was my secret – no one i knew had seen it when it came out. I will always always watch the end of it if its on tv) .
add Kinky Boots and Cool Runnings
To Sir with Love
The Last Picture Show
Music & Lyrics
My Brilliant Career
The Pillow Book
Hallam Foe
A Year Ago in Winter
Tristan & Isolde
Blow-up
While You Were Sleeping
42-Up
Straw Dogs (1971 version)
Once
I Married a Shadow
The Station Agent
Serendipity
Frozen River
H reminded me. I love movies about making movies and I watch them over again and again…
I mentioned Day for Night and Sullivans Travels but also:
The Bad and the Beautiful
Shadow of the Vampire
Ed Wood
Swimming with Sharks
I just watched Day for Night this evening for the umpteenth time.
To Kill a Mockingbird - first movie I watched again & again as a child
Forest Gump
Shawshank Redemption
The Green Mile
Good Will Hunting
As Good As It Gets
A Beautiful Mind
Gladiator
A few Alfred Hitchcock films
Dr. Strangelove
12 Angry Men
Tinker Taylor Soldier Spy
The Constant Gardner
Star Wars (all with my son)
Star Trek ( " )
Dr. Zhivago
Trip to Bountiful
The Bourne movies
Zodiac
Seven
Paris Texas
a few Jack Nicholson movies
The Pledge
The Eagle
Katherine Hepburn films
The Grapes of Wrath
Matix
Interstellar
There’s more. I’m surprised.
Happy to see so many of my favorites on the lists!
It Happened One Night
Sabrina
Roman Holiday
Philadelphia Story
Rebecca
Vertigo
To Catch a Thief
Really all Hitchcock movies
Double Indemnity (time to watch that again! Thanks for reminding me!)
Thin Man, yes. So i might as well admit, Three Stooges.
Love Legally Blonde.
Pride and Prejudice (Colin First and Keira Knightly versions)
Rebecca
Amadeus
Moonstruck
The Hunt for Red October
Dr. Zhivago
Gone with the Wind
Fiddler on the Roof
West Side Story - actually most musicals
You’ve Got Mail
My Big Fat Greek Wedding
The Godfather I, II, III
Top Gun
Home Alone
On Golden Pond
…And I’m sure there are others I’m not thinking of at the moment…
The Good, The Bad, and The Ugly
Godfather I, II, III
Dr Zhivago
Amadeus
War and Peace, any version
John Adams
Troy
Das Boot
Titanic
Exodus
A Few Good Men
Scent of a Woman
Good Will Hunting
The Imitation Game
Saving Private Ryan
The Longest Day
Gandhi
Tora Tora
The Ten Commandments
The Schindler List
Sumurai Trilogy