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The Hollywood Insider Fall Movies

Photo: ‘When Harry Met Sally’

Between gazing upon colorful foliage, frolicking through pumpkin patches, chugging apple cider, and trick or treating, you might find some time to indulge in some classic fall movies. 

In no particular order, here are some of the spookiest and prettiest fall movies to watch this autumn as the leaves change:

Hocus Pocus’

The 1993 film has been a Halloween cult classic since its release. If you’re looking for a fun-for-the-whole-family movie to throw on and take you back to your childhood, the Sanderson Sisters are just the witches for the job. Starring Bette Midler and Sarah Jessica Parker, this classic has all the hijinks and adventure you want in a classic 90’s flick. More exciting, ‘Hocus Pocus 2’ is also out this fall on Disney+.

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Dead Poets Society

‘Dead Poets Society’ has long sent ripples through the culture since its 1989 release. Its backdrop of the ecstatic Vermont foliage is maybe unmatched in movie history. As the seasons change, so do the boys of Welton Academy. In perhaps Robin Williams’s finest role, John Keating begins teaching at an elite prep school, where ancient traditions and high expectations keep its students in line. He uses his unorthodox and inspired methods to show his students another, more invigorated way to live life.

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October Sky

Based on a true story, this 1999 film follows Homer Hickham during the height of the space race. The son of a West Virginia coal miner, Homer (Jake Gyllenhaal) spots Sputnik in the night sky, inspiring his journey to become a NASA engineer to hopefully find a better life. Set in Appalachia, the film has a deep relationship to its setting, and the October sky is just one of the many beautiful natural elements of this film.

Planes, Trains and Automobiles

If you’re looking for something a little closer to the end of the fall season, look no further than this 1987 Thanksgiving classic. Starring Steve Martin and John Candy, this begrudging buddy comedy is maybe the best of John Hughes’s storied work. With laughs, mishaps, and signature John Candy wholesomeness, this feel-good movie plays on the darkness of late fall, and the light we can bring to it.

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Good Will Hunting

You knew this one was coming. ‘Good Will Hunting’ marks the world’s introduction to Matt Damon and Ben Affleck, as well as another memorable, award-winning role for Robin Williams.  This 1997 story of a genius IQ janitor and his troubled past has bewitched audiences since they first saw it. Boston is practically its own character in the film, and its autumn setting makes for particular beauty in scenes like Robin Williams’s monologue, which has since become one of the most iconic scenes in history. Make sure to revisit this classic this fall, but if you have to see about a girl, I’ll understand.

It’s the Great Pumpkin, Charlie Brown

If you’re looking for a dose of Halloween nostalgia, it may be time to revisit the Peanuts crew. The 1966 film finds Linus patiently awaiting the Great Pumpkin to rise above the pumpkin patch on Halloween night. Despite his friend’s doubts, Linus keeps faith that his supernatural pumpkin will appear. It’s a magical short film with the right amount of spooky that you can’t help but feel like a kid again after. Charles Schulz lives on!


The original Mike Myers movie is a slasher classic, and Jamie Lee Curtis manages to not only fight off a supernatural serial killer, but start a famous movie franchise. If you’re looking to scare yourself into a memorable fall night, one of the baker’s dozen ‘Halloween’ films they’ve made. ‘Halloween Ends’ is also out this fall and marks the end of an era that will see Curtis and her arch-villain square off for the final time.

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If Beale Street Could Talk’

Barry Jenkins does it again with his envisioning of 1970s Harlem in the fall. The movie is based on the 1974 novel by James Baldwin and follows Tish (Kiki Layne) as she and her family seeks to prove the innocence of her friend and lover Fonny (Stephan James). It’s a beautiful and nostalgic trip down memory lane as the seasons change in New York City. Walk down Beale Street for a full trip down memory lane. 

When Harry Met Sally…’ 

Another New York City classic. Despite the fact this movie takes place over the course of years, one iconic scene finds the pair in Central Park. The color, the foliage, and the romance of the city in autumn permanently make this quintessential romcom a fall classic. Billy Crystal and Meg Ryan’s 1989 movie contemplates the question “can a man and woman ever just be friends?” but fails to resolve it. Do yourself a favor at least, and enjoy asking the question by revisiting this one.

By Patrick Lynott

Click here to read The Hollywood Insider’s CEO Pritan Ambroase’s love letter to Cinema, TV and Media. An excerpt from the love letter: The Hollywood Insider’s CEO/editor-in-chief Pritan Ambroase affirms, We have the space and time for all your stories, no matter who/what/where you are. Media/Cinema/TV have a responsibility to better the world and The Hollywood Insider will continue to do so. Talent, diversity and authenticity matter in Cinema/TV, media and storytelling. In fact, I reckon that we should announce “talent-diversity-authenticity-storytelling-Cinema-Oscars-Academy-Awards” as synonyms of each other. We show respect to talent and stories regardless of their skin color, race, gender, sexuality, religion, nationality, etc., thus allowing authenticity into this system just by something as simple as accepting and showing respect to the human species’ factual diversity. We become greater just by respecting and appreciating talent in all its shapes, sizes, and forms. Award winners, which includes nominees, must be chosen on the greatness of their talent ALONE.

I am sure I am speaking for a multitude of Cinema lovers all over the world when I speak of the following sentiments that this medium of art has blessed me with. Cinema taught me about our world, at times in English and at times through the beautiful one-inch bar of subtitles. I learned from the stories in the global movies that we are all alike across all borders. Remember that one of the best symbols of many great civilizations and their prosperity has been the art they have left behind. This art can be in the form of paintings, sculptures, architecture, writings, inventions, etc. For our modern society, Cinema happens to be one of them. Cinema is more than just a form of entertainment, it is an integral part of society. I love the world uniting, be it for Cinema, TV, media, art, fashion, sport, etc. Please keep this going full speed.

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