I've seen Overboard a few times, but not purposely, though it is a good movie. As for wanting to watch more than once:

Dirty Dancing

Smokey Mountain Christmas

Hunt for Red October

Christmas Card

I'm sure there are more, but I can't think of them right now.

Ditto, Dirty Dancing, the Tom Hanks one alone on that island, The Rose, Beach Music, Pretty Woman, altho I've seen it many times, and more, as you all remind me!

The Wizard of Oz, Beaches, Mrs. Doubtfire, The Bird Cage.

While You Were sleeping

Pretty Woman

I too have seen Overboard a lot (I think it gets heavy rotation because it's a family movie but with grown up content)! I have this theory about which movies are best watched over and over and most of them are ones that go from "good bit" to "good bit". They don't have to be great movies. They just need to have enough good bits that hold up to repeated viewing. Of the ones mentioned, I have seen Pretty Woman more than 5 times, but I can't watch it anymore. I wore out the good bits. :) Also have seen and could see again, the first three Star Wars (4-6) and Star Trek 4 (which is a hoot) and While You Were Sleeping. Others:

The first three Matt Damon Bourne movies

The first three Harry Potter movies

The Big Easy

Desperately Seeking Susan

Mary Poppins

Serenity (Firefly)

O Brother Where Art Thou? (which is a hootnanny)

I'm sure there are more. The first ones I've listed are the kind I'll watch again if I'm poking around and looking for something to watch on TV. The last five are some of my all time favorite movies. Interesting...four are music heavy. :)

Going back a bit farther, there are also:

Heidi with Shirley Temple

Topper

Harvey

Meet Me in St. Louis

The Thin Man

Sitting Pretty

Father of the Bride and Father's Little Dividend

The Philadelphia Story

It Happened One Night

Desk Set

Arsenic and Old Lace (Cary Grant version)

Yes to Dirty Dancing. Also on my list would be The Usual Suspects, Leon the Professional, Ice Castles,Paint Your Wagon, The Lost Boys, Rocky Horror Picture Show, Weird Sisters and the Police Academy ones and early Whoopie Goldburg flicks. DD and I used to have old Gidget movie dates and now 3 year old DGD who is me watch Teen Beach Movie over and over. I love it because she sings and dances along to it. She rocks it. LOL Apparently I will be watching a lot of Home. It is 20 month old DGS's current favorite.

I second Serenity and have more trash to add as having seen more than 5 times and that is all the Ocean's (George Clooney) movies.

Oh yes, who can pass up Arsenic and Old Lace! So many more you've all reminded me of, love Jamie Lee Curtis in True Lies!

Oh goodness, it seems there are too many to list.

Singing In The Rain

Holiday Inn

White Christmas

Royal Wedding

My Fair Lady

Breakfast at Tiffany's

Almost every Disney movie

The Wizard of Oz

All the Star Trek films

All the Star Wars films

All the Stargate films

All the Marvel Universe films

All the Harry Potter movies

The Ref

The Family Stone

All the Christmas classic cartoons by Rankin Bass

Quigley Down Under

The Terminal

A League of Their Own

Snatch

Seven

Plus almost every movie already listed, While You Were Sleeping, Pretty Woman, Dirty Dancing, True Lies and many, many more.

My family has always loved films. We have a family game where we will say a (hopefully obscure) quote from a movie and the others have to guess which movie it is.

5 times? Nothing recent, but a couple of oldies. African Queen, and Bridge on the River Kwai ;) I may have seen Dr. Zhivago about 3.

But then I think I've seen Jaws about three times, and Perfect Storm. Do you notice something of an ocean theme going there ;)

Dirty Dancing

Grease

Rocky movies

Freaky Friday

She's the Man

Toy Story

Ok, but this is going to be a long list!

The groups include: LOTR, Indiana Jones, Harry Potter, MIB, Star Wars, Matrix, Bourne Identity, Pirates of the Caribbean, Disney/Pixar Animated, and many of the British Classics.

Romancing the Stone/Jewel of the Nile, Breach, Babe, While You Were Sleeping, The Count of Monte Cristo (2002), Mr & Mrs Smith, King's Speech, Braveheart, Butch Cassidy and the Sundance Kid, The Sting, Karate Kid, My Fair Lady, Capote, Murphy's Romance, Lust Caution, Good Morning Vietnam, Last King of Scotland, Dangerous Liaisons, Two Weeks Notice, Speed, Ghost, Homeward Bound, Hunt for Red October, Pride & Prejudice (2005), Spaceballs, Rabbit Proof Fence, Quills, Honey I Shrunk the Kids, Joan of Arc (Leelee Sobiesky), The Tailor of Panama, Tea With Mussolini, Catch Me if You Can, Life is Beautiful (subtitled only!), V for Vendetta, War Horse, Being John Malkovitch, Shawshank Redemption, 50 First Dates, Pans Labyrinth, When Harry Met Sally, Sleepless in Seattle, The Music Man, As Good as it Gets, Jumunji, Amadeus, Blow, Charlie Wilson's War, Blood Diamond, Big, African Queen, The Truman Show, The Blind Side, Liar Liar, Home Alone, All the President's Men and the two Sherlock Holmes Movies (2009 & 2011).

Some of our movie collection is out on loan, so I am sure there are forgotten titles.

Plllog, I agree with you about the good bits. I have favorite movies, but I tend to watch just the parts that I like and fast-forward through the rest. So, some of my favorites aren't great movies, but they have some good bits in them. I like way, way more than five, but if I could only have five, they would be:

The Slipper and the Rose

Grease

Three Men and a Baby

The American President

Star Trek (the reboot with Chris Pine)

Please let me know if you see any type of theme in my list. :D

All the movies of....

William Powell

Spencer Tracy

Clark Gable

Cary Grant

Marlon Brando

Audrey Hepburn

Katherine Hepburn

Jack Lemmon

Glenn Ford

Rita Hayworth

Humprey Bogart

Paul Newman

Steve McQueen

John Garfield

Kirk Douglas

Doris Day

Edward G Robinson

The Gods must be crazy

You've reminded me of some more 5+ers: The American President, Two Weeks Notice, The Blind Side, and Babe (Wolf!! Wolf!!!). There are a lot on Gyr_Falcon's list that I really like, and some are brilliant, but that I don't feel like I have to to watch again just because it's on. :) GyrF, I think the theme there is danged good movies!

Pretty much any/ALL musicals.

Harry Potter series

You've Got Mail

Sleepless in Seattle

All the Disney animated movies

Apollo 13

Independence Day

Men in Black

It's a Wonderful Life

These would all be in the privacy of my own home. It is RARE I would go to the Theater once let alone more than that for a movie.

Another vote for Dirty Dancing, also Ghost. Mrs. Doubtfire.

Robin Williams, Patrick Swayze--sadly, both gone.

The Notebook (and I still cried every time)

Mr. and Mrs Smith......every time I watch it, I catch something that I missed before

Four Weddings and a Funeral

Forrest Gump

Grease

A Fish Called Wanda

Monty Python and The Holy Grail

Bridget Jones Diary

And the Truman Show.

Bull Durham

An Officer and a Gentleman

Pretty Woman

Dirty Dancing

Urban Cowboy

Ghost

I don't usally watch movies more than once. So many movies so little time.

Ghost

Blues Brothers

Ghostbusters

Phantom of the Opera

J. C. Superstar

West Side Story

Sound of Music

The Music Man

Marx Brothers movies

W.C. Fields movies

Mae West movies

Thin Man movies

Shining Through (Love that movie!)

all The Alien movies

all the Predator movies

John Wayne movies, especially with Maureen O'Hara in them like The Quiet Man and Big Jake

Bourne movies

Silverado

Dances With Wolves (Love it)

Hunt for Red October

U571

Thor

The Avengers

Steel Magnolias, the original from 1989 I believe (Love it)

love disaster movies, like 2012, Titanic, Poseidon Adventure, 28 Days Later, Day After Tomorrow....... kinda morbid huh? haha

so many more I'm sure.......

edited to add

The Count of Monte Cristo

A League of Their Own

Mr. & Mrs. Smith

Legends of the Fall

Interview with the Vampire

5th Element

Cowboys & Aliens

Twlight series...

I am number 4

Predator series

Ironman series

Flash Dance

Sound Of Music

Ice Age

How To Train Your Dragon

Men In Black...

My Cousin Vinny

Funny Girl

What's Up Doc?

Oklahoma

ETA:

Bridges of Madison County

Same Time Next Year

The Shining

As Good As It Gets

Nemo

The Bird Cage

Harold and Maude

My Favorite Year

My Favorite Year

My Favorite Year

My Favorite Year

My Favorite Year

In no particular order...

Koyaanisqatsi

A Christmas Story

Miracle on 34th Street (the original with Natalie Wood)

Dirty Dancing

O Brother Where Art Thou?

Cool Hand Luke

Same Time, Next Year

Breakfast at Tiffany's

Harold and Maude

Beaches

Two for the Road

Same Time, Next Year

Dirty Dancing

Sweet Home Alabama

Notting Hill

Pretty In Pink

The Holiday

Love Actually

(I'm a sucker for lovey dovey movies)

A Christmas Story (but only at Christmastime)

O Brother Where Art Thou?

Top Gun

St. Elmo's Fire

Breakfast Club

Christmas in Connecticut

Christmas Story

National Lampoons Vacation/European Vacation/Christmas Vacation

Harry Potter (all of them)

About Last Night

About a Boy

Notting Hill

Nicole, which Fifth Element? I can infer others from context, but with your list it could be either one...

Y'all have reminded me of more on my list: Apollo 13, Bull Durham, My Cousin Vinny. Top Gun is another one that used to be on the list but isn't anymore. Since I run the TV for company while I work, there are a lot of things I've seen many times, so by my own criteria, I'm only listing those which I'd stop to watch if they came on right now. :)

Also:

Space Cowboys

Barefoot in the Park (Jane Fonda/Robert Redford)

The Parent Trap (Hayley Mills)

You Can't Take It with You (both the Jimmy Stewart movie version and the Jason Robards TV production of the original play)

Deathtrap, if it's long enough between viewings to forget what exactly is happening

Dead Again

My answer I guess would be quite a bit different. Even if I REALLY like a movie, I have no interest in watching it again until decades go by. I'm currently watching movies again on DVD that I first & last saw in the 1970ties but are somewhat vague in my mind....Alice Doesn't Live Here Anymore, Paper Moon, etc. & will probably never watch them again in my lifetime. I sometimes purchase DVD's at garage sales, but donate them to our public library after viewing. Never understood the Christmas tradition of viewing It's A Wonderful Life over & over & over.

In no particular order:

The Longest Day

The Dirty Dozen

The Blind Side

Independence Day

Singing In The Rain

Bull Durham

Major League

Some Like It Hot

The Music Man

Shawshank Redemption

The Spirit Of St Louis

Apollo 13

The Greatest Game Ever Played

Armageddon

Priscilla Queen of the Desert

Thelma and Louise

Muriel's Wedding

10

Being There

Big

Polar Express

(I don't really like movies and seldom see them esp since I became a widow 20+ years ago and lost my built-in date).

I find it interesting to see the list of others. Several of those mentioned I had not considered; but in reality I have seen more than several times.

The Music Man

Airplane

Blazing Saddles

Who's Afraid of Virginia Wolfe

Others I have seen more than once, but don't qualify for the question.

plllog...with Bruce Willis as Korben Dallas. I would love to see another one....?

I just remembered to add:

Scorpion King

Independence Day

I am Legend

I love and re-watch many of the movies already mentioned. One I haven't seen listed is Moonstruck, a movie that I re-visit more than any other.

How could I forget My Cousin Vinny and The Bird Cage!

Surprising how many of us like many of the same movies!

Nicole, my bad. There was a lot of buzz a couple of years ago, and I thought I'd seen something about it going into production, but apparently, that was just a whole dust storm of gobbledegook spun out of nothing. Or, at least, so it seems from looking on Google. I had heard a whole rundown of what the new film would be, and how different it was from the original, and something about the marketing plan. It seems to be cinematic vaporware! The only things that come up on several searches are an interview with Luc Besson about how he made the film just before a technological leap in special effects and how he wished he had another crack at it, and that being spun in other places as he wanted to do a sequel or remake, and also a press release that Benedict Cumberbatch had signed to do The Fifth Estate, which was subsequently misquoted to say Fifth Element. So I don't know what the heck was with the marketing plan, but turns out there is no remake. :)

The Godfather

My Cousin Vinny

Best in Show

Back to the Future (trilogy)

My Big Fat Greek Wedding

Being There

Field of Dreams

Grease

One I remembered was Air Force One and you reminded me of Independence Day which I saw for the first time about 18 months ago and I have seen it 5 times since.

Zero. I am certain I have never intentionally watched ANY movie more than three times, and I am approaching 75. (Sometimes stuff like "Easter Parade" or "White Christmas" drops into your life for a few minutes until you change the channel.) I have never bought a DVD of a movie.

This may be explained by our ability to get interesting *new* movies and TV series on DVD from our local library -- and now, to stream *new* things via Amazon Prime.

I suppose that before too long I *will* watch movies over and over, because my aged brain will not remember that I've seen them! Laughter is supposed to be good for you; maybe I'll have an endless loop of comedies.

(I seldom re-read a book, either.)

I am sure I have not watched any movie five times, but ones I have seen more than once are, O Brother Where Art Thou, A Christmas Story, and Forrest Gump. There could be some others. I am not into watching a lot of television for the most part or watching videos at all.

Sue

We saw Guardians of the Galaxy 3 times in the movie theater, and countless times on bluray at home.

Love love love, Legends of the Fall...so beautiful

Rocky Horror Picture show

Wizard of Oz...my very favorite older movie

I think I'll look back on this thread for a long time! Now when I want to watch something this will be my go to info. Thanks every one! Kathy G in MI