Fall into Film: Your Seasonal Movie Guide 

 Set in Boston, Good Will Hunting surrounds itself with the fall aesthetic, while making you laugh, cry and catapult you into a picturesque collegiate world.

Will Hunting is a boy with a very high IQ, but due to different life circumstances, he works as a janitor at MIT. One night, while bored on the job, he solves an insolvable math problem. He piques the interest of a well-known professor who crafts out different opportunities for him and sets him up with a therapist who takes him on a journey of self-love and acceptance.

This film centers around friendship, love, and untapped potential that not only has you rooting for the little guy but also lends you a different perspective on intelligence. 

Throughout Dead Poets Society, we follow the lives of teenage boys while they attend a preparatory school. Their goal is to be the best of the best, living up to the school’s high standards and their parents’ even higher expectations.

However, when a new teacher enters their lives, they gain a new lease on life and academia. He teaches them to see things differently, to explore outside of the bubble they’ve lived most of their lives in and to seize the day.

This movie acts as a time capsule of inspiration and ambition. It grabs on to us and, through the character of Robin Williams, yells at us to embrace our innate artistry because a world without creativity is a sad world indeed.

If anyone calls your phone asking you, “What’s your favourite scary movie?”, do yourself a favour and hang up!

This classic slasher movie follows American teenager Sydney Prescott as she navigates life in her suburban town after her mom’s death a year prior, with the ominous threat of a masked killer on the loose. Scream pokes fun at the typical cheesy scary, making the film equal parts horror and comedy, which is why it stands the test of time and remains one of the best spooky season watches.

I highly recommend putting this at the top of your Halloween movie night watchlist. As we head into the spooky season, and is the perfect way to dip your toe into the horror genre during fall. 

This Wes Anderson film uses its quirky dialogue and dry humour to catapult you into an animated world of satirical wit. Although it might be an animated film, Fantastic Mr. Fox conveys a sophisticated message that, through one’s struggle with identity, we must find a balance between desire and responsibility, as too much of either is destructive.

We can see that the plot unfolds as Mr. Fox struggles between his own animal instincts and his responsibilities to his family and community. 

While all the Harry Potter films are an absolute binge for the fall season, the best place to start is with the first one, Harry Potter and the Sorcerer’s Stone. At the ripe age of eleven, Harry discovers that he’s a wizard and is whisked off on a wild adventure to Hogwarts, where he makes life-lasting friends (and enemies).

He goes on a journey of self-discovery and begins to feel at home for the first time since his parents died when he was a baby. Through this new chapter in Harry’s life, he begins to learn more about the tragedy that was his parents’ death and about the person who took it and how he falls into the middle of it. This is a movie that’s fun at any age, and whether you’re a Hufflepuff, Gryffindor, Ravenclaw or Slytherin, it will have you wishing Hogwarts was a real place that you could apply to.

Tim Burrton never disappoints, combining the slight chilliness of fall and the spookiness of Halloween. The Nightmare Before Christmas follows Jack Skellington, Holloweentown’s most popular resident, as he becomes bored with his everyday life of scaring people.

When he accidentally comes across Christmastown, his interest is piqued by the joyful environment and the different color lights. Jack decides that the only way to get out of the rut he’s in is to kidnap Santa and take over Christmas Town, but his plan quickly turns sour as he realizes that maybe Santa cannot be replaced and perhaps he was better off before he caused all this chaos. 

Nora Ephron’s classic rom-com When Harry Met Sally follows Harry and Sally throughout twelve years of their lives, testing the theory if men and women can just be friends. Meeting on three separate occasions and then embarking on a platonic friendship with one another, Harry and Sally help each other through their different stages of singleness.

My personal favourite part of the film is the real-life testimonials interspersed throughout the film from real couples who share their story of how they found true love within each other. This enemies-to-friends-to-lovers movie will make you feel every possible emotion, and it does it by giving off the essential cozy vibes that make it the perfect film for fall.

Literary classic, Little Women, has been adapted several times; however, Greta Gerwig’s 2019 adaptation is by far my favourite. Follows the March sisters as they navigate adolescence and transition into adulthood in a post-Civil War era. Each sister yearns to live a different type of life than the other, whether it’s being an independent writer in New York, marrying for love and having a family, studying art in Paris or dedicating their time to piano.

As they succeed and struggle in their chosen paths, they are reminded that their first loves were each other, and as their lives ebb and flow, we see just how unforgiving it is to be a woman with different desires and aspirations. This movie just grabs onto you, not letting you go until you feel like just maybe you were a March sister in another life.

I might be a bit biased because this is my favourite movie ever made, but everybody should watch this movie at least once in their lives! And fall is the perfect season to do so. Almost Famous follows a 15-year-old boy named William as he tries to pursue a career as a music journalist.

He lands a gig with Rolling Stone magazine, doing a story on an up-and-coming band named StillWater, and ends up shadowing the band as they embark on a tour. Dealing with life on the road, the new friends he makes along the way and his true unbridled passion for the music, William has never been happier until he realizes that it may not be as rock and roll as it seems.

If you’ve ever wanted to be a groupie for your favourite band, then this movie is for you. The music, the love, but most importantly, the pure rockstar essence will leave you staring at the screen, asking for more. 

Practical Magic follows two polar opposite sisters, Sally, played by Sandra Bullock, and Gillian, played by Nicole Kidman, who happen to be witches. Raised in a small town that holds its prejudices against them, and dealing with a curse that is supposed to prevent them from falling in love, these two sisters have a lot on their plates, especially when a detective comes to investigate them for the death of one of their ex-boyfriends.

It’s the perfect spooky chic flick with a spell book I’d like to borrow and use on my own ex-boyfriend. And… who doesn’t want to make midnight margaritas with their girlfriends! This film encapsulates the spookiness of Halloween and the comfort of fall.