Falling for Film: A Handpicked Selection of Autumn Movies
Written by Amani Rizwan
When Harry Met Sally (1989) by Columbia Pictures
Picture this: rust-coloured and burnt orange leaves falling onto the ground as you walk across damp puddles, remnants of the rain from the night before. There’s a slight, but crisp breeze that nips at your face, and has your hands digging deeper into the warmth of your jacket in a very Bob-Dylan-Freewheeling-esque manner. The sun is setting and you can feel summer slipping away into the horizon as the promise of a bitterly cold winter tugs at the air. Still, right now, nothing can go wrong at a temperature of approximately 17 degrees Celsius as you trudge on to your humble abode. There, a warm soup awaits you, as does a fluffy sherpa blanket in front of the TV.
And what better to settle into than the perfect fall film like When Harry Met Sally, with its strolls through New York’s autumn foliage, or Dead Poets Society whose dialogue and ambience perfectly wrap you in the quiet magic of the season? Listed below are a few more movies to help you sink further into the autumn mood as the days get shorter and the nights longer.
These movies have not been ranked.
Good Will Hunting (1997)
“Real loss is only possible when you love something more than you love yourself.”
Written by Matt Damon and Ben Affleck when they were in their early 20s, Good Will Hunting tells the story of Will Hunting (Matt Damon), a genius-level intellect working as a janitor at MIT. Though he can solve complex mathematical problems effortlessly, Will struggles to overcome the emotional scars of his past. With the help of an empathetic therapist (Robin Williams) and the support of his loyal best friend (Ben Affleck), Will embarks on a journey of self-discovery and healing. It’s a gripping tale, drenched in burnt orange and yellow hues, about friendship, vulnerability, and the courage it takes to change. Available on Prime and for rent on Apple TV.
Coraline (2009)
“When you're scared but you still do it anyway, that's brave.”
Based on Neil Gaiman's novella, Coraline is an absolute fall classic. It’s a stop-motion animated adventure about a young girl (voiced by Dakota Fanning) who discovers an eerie parallel world where everything seems better, until the truth of this new world is revealed. Directed by Henry Selick, this dark fantasy is a mesmerising exploration of courage, family, and the perils of yearning for a different life. Featuring striking visuals and a haunting score, it’s the perfect autumn treat that captivates viewers of all ages. Available on YouTube Movies and for rent on Apple TV.
Days of Heaven (1978)
“Nobody’s perfect. There was never a perfect person around. You just got half-devil and half-angel in you.”
Terrence Malick’s Days of Heaven is a visual masterpiece, a poetic exploration of love and betrayal set against the stunning landscapes of early 20th-century America. Starring Richard Gere, Brooke Adams, and Sam Shepard, it tells the story of a labourer who, with his lover, conspires to cheat a wealthy farmer. The film’s sweeping and breathtaking imagery — dusky skies, golden wheat fields, and the fading light of the afternoon mirror the beauty of fall. Its quiet meditations on life, death, and impermanence make it a classic, even more so in autumn. Available on Criterion Channel and for rent on Prime.
When Harry Met Sally (1989)
“I'll have what she's having.”
No fall movie list is complete without a Meg Ryan rom-com, especially this one. Directed by Rob Reiner and written by Nora Ephron, When Harry Met Sally follows the evolving relationship between two friends, Harry (Billy Crystal) and Sally (Meg Ryan), as they debate whether men and women can truly be just friends. It’s a delightful romantic comedy filled with witty dialogue, great memorable moments, and even greater sweaters. And if you’re looking for the perfect double feature, You’ve Got Mail is the perfect accompaniment. While When Harry Met Sally explores friendship and love over the years, You’ve Got Mail captures a modern twist on serendipity with anonymous emails leading to an unexpected romance. Both films are set against the cosy, autumnal background of New York and make for the perfect lazy Sunday. Available on HBO Max and for rent on Apple TV.
Fantastic Mr. Fox (2009)
“If what I think is happening, is happening, it better not be.”
Wes Anderson’s Fantastic Mr. Fox is a quirky stop-motion adaptation of Roald Dahl’s children’s novel. Voiced by George Clooney, Meryl Streep, and Jason Schwartzman, it follows the titular Mr. Fox as he plans one last heist against three evil farmers. The film's vibrant orange visuals, offbeat humour, and touching themes of family and identity make it the perfect movie to curl up on the couch and watch with a hot chocolate. Available on Disney+ and Prime, and for rent on Apple TV.
The Aviator’s Wife (La Femme de l'aviateur) (1981)
“Personally, I like life when it’s most like a novel”
Directed by Éric Rohmer, The Aviator’s Wife is a French romantic drama centred on the complications of love and misunderstanding. When François (Phillipe Marlaud), a young postal worker, suspects his girlfriend of infidelity, he follows her ex-lover through Paris, leading to a bittersweet reflection on relationships and jealousy. It's a subtle, introspective film, with Rohmer’s signature focus on dialogue and human emotion. Available for rent on Amazon.
October Sky (1999)
“We’re not gonna blow ourselves up, are we?”
Based on a true story, October Sky follows Homer Hickam (Jake Gyllenhaal), a coal miner's son, who dreams of building rockets instead of following in his father's footsteps. This inspirational coming-of-age drama, directed by Joe Johnston, highlights perseverance, the importance of education, and how one small-town boy reached for the stars. Available on Prime and for rent on Apple TV.
Big Eyes (2014)
“He sold paintings. I painted them.”
Tim Burton’s Big Eyes tells the real-life story of Margaret Keane (Amy Adams), whose iconic paintings of large-eyed children became a phenomenon in the 1960s. However, it was her husband, Walter (Christoph Waltz), who took the credit. The film is a fascinating exploration of art, deception, and female empowerment. Available on PLEX and for rent on Apple TV.
Parachute (2023)
“You can’t fall if you never jump.”
Parachute, Brittany Snow’s directorial debut, is a sensitive indie drama that explores the delicate balance between love and addiction. Starring Courtney Eaton and Thomas Mann, it follows Riley and Ethan, two twenty-somethings grappling with their own emotional struggles, who find solace in each other. Their relationship forces them to confront difficult truths about dependency and healing. They also play Marry Me, Archie by Alvvays not once, but twice in this; if that isn’t enough reason to watch it, I don’t know what is. Available on VOD platforms like Apple TV and Prime.
Dead Poets Society (1989)
“Carpe diem. Seize the day, boys. Make your lives extraordinary.”
Last but definitely not least is what I consider the quintessential fall movie — Dead Poets Society. Robin Williams stars as an unconventional English teacher, who urges his group of school students to embrace their passions and break free from societal expectations. Set against the backdrop of a 1950s picturesque prep school and directed by Peter Weir, this poignant drama explores themes of individuality, rebellion, and the consequences of pursuing one's dreams. Available on Disney+ and for rent on Amazon and Apple TV.
Honourable mentions:
James and the Giant Peach, Little Women, Awakenings, After Yang, Stepmom, Practical Magic, and Beginners.
These films, whether through their toasty, earthy colour palettes, or introspective themes, each encapsulate something or the other about the season of change. After all, fall isn’t just about the physical change in the weather — it’s about transitions, reflections, and the bittersweet feeling of letting go and welcoming something new in its stead. Whether you enjoy the whimsicalness of films like Coraline, or the emotional journey of movies like Good Will Hunting and Parachute, these movies are the perfect escape as autumn settles in and the world slows down.