From a thread on UnschoolingDiscussion list came this collection of "unschooly-type nonconformist movies."

 

Jessie

Nim's Island

A young girl inhabits an isolated island with her scientist father and communicates with a reclusive author of the novel she's reading. Which is very unschooly and promotes trusting a child in a way so many parents wouldn't even consider.

 

Rocco

Off the Map

If ever there was one, this is it. It reminded our family of a lot of things we needed to be reminded of. Check it out! -- An 11-year-old girl watches her father come down with a crippling depression. Over one summer, she learns answers to several mysteries and comes to terms with love and loss.

 

Alison

My Family and other Animals

An English family relocates to sunny Greece four years before WWII.

Son of Rambow

During a long English summer in the early 1980s, two schoolboys from differing backgrounds set out to make a film inspired by First Blood (AKA Rambo).

 

Julie

One Flew Over the Cuckoo's Nest

Upon admittance to a mental institution, a brash rebel rallies the patients to take on the oppressive head nurse.

A Room with a View

About a young woman in the repressed culture of Edwardian era England as women were on the cusp of beling allowed more independence.

Cool Hand Luke

Arrested on a minor charge, a man refuses to submit to the inhuman system in a rural prison.

Harvey

Imagination and delight in a stuffy, proper world.

Being There

Simplicity trumping schooled professionalism, uneducated main character, unabashed delight in TV.

Forrest Gump

Simplicity and joy, cultivating a variety of interests, succeeding despite schooly definitions/expectations, having a strong parent advocate/ally.

 

Nancy B

Good Will Hunting

Adult in many places, but great movie about doing things your own way.

Finding Nemo

Letting kids go and trusting them.

Can't Buy Me Love

Being yourself. A nerdy outcast secretly pays the most popular girl in school one thousand dollars to be his girlfriend.

Chocolat

Never shows the girl going to school, letting your child learn from surroundings, letting kids and selves be free.

Scent of a Woman

More anti-school maybe, than unschooling, but sooooo good!

The Secret of Roan Inish

probably one of THE BEST unschooling movies there is. A young girl is sent to live with her grandparents near the island of Roan Inish where she explore the legend that her younger brother was swept away in his infancy and raised by a selkie.

Uncle Buck

More anti-school, but also being yourself, having fun, doing things differently.

 

Amy Bowers

The Wild Parrots of Telegraph Hill

The subject, Mark Bittner, seems to be living an unschooling life. He is really smart, and totally utilizes institutions only when he needs them - the rest of the time he is creating the life he wants and searching for his peace and creative sustenance.

To Kill a Mockingbird

Kids learn so much from life around them. A coming of age story centered around a noble lawyer's defense of a wrongly accused black man in the prejudiced South as seen through the eyes of his young daughter.

 

Sandra Dodd - My longtime list of movies that will help with deschooling:

Mary Poppins

An unconventional nanny stirs up the lives of a distant banker and his family.

Heidi - with Shirley Temple.

A plucky orphan girl gets dumped abruptly into her gruff, hermit grandfather's care.

The Sound of Music

A woman leaves an Austrian convent to become a governess to the children of a distant widowed Naval officer.

Searching for Bobby Fischer - "Innocent Moves" is the British title.

A young chess prodigy refuses to harden himself in order to become a champion like the famous but unlikable Bobby Fischer.

Ferris Bueller's Day Off

A popular high school senior is determined to have one more day off from school and show his depressive friend there's life beyond his fears.

 

Linda

Curious George

I was amazed at how overtly unschooly it was! George is an inquisitive pet monkey whose enthusiasm and curiosity lead him on wild adventures.

 

Robyn Coburn

Kiki's Delivery Service

A young witch, on her mandatory year of independent life, finds fitting into a new community difficult while she supports herself by running an air courier service.

Castle In The Sky

A young boy and a girl with a magic crystal must race against pirates and foreign agents in a search for a legendary floating castle.

 

Schuyler

Whale Rider

A contemporary story of love, rejection and triumph as a young Maori girl fights to fulfill a destiny her grandfather refuses to recognize.

The Story of the Weeping Camel

When the rare white bactrian camel calf of a Mongolian nomadic family is rejected by its mother, a musician is needed for a ritual to change her mind.

Never Cry Wolf

A government researcher, sent to research the "menace" of wolves in the north, learns about the true beneficial and positive nature of the species.

 

Elaine - Mostly they are movies that make you think.

Rabbit-Proof Fence

In 1931, three aboriginal girls escape after being plucked from their homes to be trained as domestic staff and set off on a trek across the Outback.

The Incredible Shrinking Man

Not the B movie it appears to be. When Scott Carey begins to shrink because of exposure to a combination of radiation and insecticide, medical science is powerless to help him.

My Neighbour Totoro

When two girls move to the country to be near their hospitalized mother, they have adventures with the wonderous forest spirits who live nearby.

Spirited Away

During her family's move, a sullen 10-year-old girl wanders into a world ruled by gods, witches, and spirits. When her parents are transformed into pigs, she must find a way to free them and herself and return home.

Whistle Down the Wind

When an injured fugitive takes refuge on a remote Lancashire farm, the owners three children mistakenly believe him to be the Second Coming of Christ.

The Snow Goose

At the beginning of the Second World War, in an Essex fishing village, Fritha, a young orphan, finds a snow goose wounded by shotgun. A hunched back artist who lives a solitary life in an abandoned lighthouse in the marshlands helps Fritha to nurse the bird back to flight.

Kes

A young, English working-class boy spends his free time caring for and training his pet falcon. Gritty and sad.

 

Danielle Conger

Chitty Chitty Bang Bang

An eccentric inventor turns a broken-down Grand Prix car into a flying vehicle for his free-spirited children, and then they go off on a magical fantasy adventure to save their grandfather in a far-off land.

 

Linda K.

October Sky

The true story of Homer Hickam, a coal miner's son who was inspired by the first Sputnik launch to take up rocketry against his father's wishes.

School of Rock

When struggling musician Dewey Finn finds himself out of work, he takes over his roommate's job as an elementary school substitute teacher and turns class into a rock band.

 

Carri Ann

Fly Away Home

A father and daughter attempt to lead a flock of orphaned Canada Geese south by air. Based on a true story.

 

Emily D.

Explorers

14yr old science whizzes build a spaceship in their homemade lab in lieu of getting beat up at school.

Goonies

In order to save their home from foreclosure, a group of misfits set out to find a pirate's ancient treasure.

Ferris Bueller's Day Off

I know someone mentioned it already but ....

 

Katy J.

With Honors

Obsessed college student meets a homeless guy and learns that there are more important things than graduating with honors. Great movie, more adult though (extremely boring to my 10yo). 

 

Sarah

Pippi Longstocking

Nine-year-old Pippi is unconventional, assertive, playful and unpredictable. She frequently makes fun of pompous and condescending adults. Like Peter Pan, Pippi does not want to grow up. She is the daughter of a buccaneer captain and as such has adventurous stories to tell.

 

Lindsay B.

Lords of Dog Town

Its an excellent movie and very unschooly. A must see for kids who have any interest in skateboarding (parents too!) Biographical drama film follows a group of young skateboarders in Venice Beach during the early 1970s.

 

Esther Ritmeester

The World's Fastest Indian

about an older guy who beats all the know-it-alls in a motorcycle race on a homebuilt do it your self motorcycle in a 'follow your dream' themed movie. Great for all the family.

Pay it Forward

About what a difference a young boy can make in the world after his teacher gives him that chance.

 

Karen/Kidgie - Both EXCELLENT unschooly movies... ;).

Rock N Roll High School

A group of rock-music-loving students, with the help of the Ramones, take over their school to combat its newly installed oppressive administration.

Harold and Maude

Young, rich, and obsessed with death, Harold finds himself changed forever when he meets lively septuagenarian Maude at a funeral.