Our all-time favorite fall films

Now that autumn is officially here, it's time to cozy up with movies like Clueless, When Harry Met Sally, The Witch, and more

By Gabrielle Sanchez  |  September 22, 2022 | 12:00pm
Film Features Films
Our all-time favorite fall films
L-R: The Witch, When Harry Met Sally, Clueless, Phantom Thread Screenshot: A24

Today marks the first day of autumn, and to celebrate the season, we’re sharing the films which make their way back into our hearts and minds every year when the leaves begin to change. For some, fall brings back memories of going back to class and enlivens the spirit of high school shenanigans. For others, it’s a season for reflection, romance, and longing. No matter what feelings arise this time of year, we’ve got you covered.

All That Heaven Allows (1955)
Jane Wyman in All That Heaven Allows

When the leaves begin to change and fall, it’s time to return to Douglas Sirk’s melodrama romance , which follows an affluent widow as she falls in love with her rugged, younger arborist. Rock Hudson and Jane Wyman are absolutely sensational in this cozy, heartfelt feature from one of the best. The story begins when Ron Kirby (Hudson) visits Cary Scott (Wyman) to shape up her trees before the winter season, and chronicles their romance through the holidays. All That Heaven Allows remains perfection in its warmth, technicolor vibrance, and deeply entrenched longing. [Gabrielle Sanchez]

Knives Out (2019)
Knives Out (2019) New Trailer – Daniel Craig, Chris Evans, Ana de Armas

In general, there’s something autumnal about a whodunnit, at least in this writer’s opinion. (Perhaps a good mystery is simply Halloween-adjacent.) But it’s not just the puzzle of Harlan Thrombey’s murder that evinces these seasonal vibes. Rian Johnson’s first movie is set against the backdrop of a New England fall (perhaps the best place in all the world to experience the season). There are crunchy leaves on the ground around the creaky, quirky mansion, roaring fireplaces, and autumn attire. Yes, Chris Evans’ cable knit sweater deserves a shout-out, but the final image of Marta (Ana de Armas) wrapped in a blanket on the balcony, sipping from her “MY HOUSE, MY RULES” mug is an all-time iconic image that screams fall. Bonus: If you watch Knives Out this fall, you’ll be prepared when the sequel, Glass Onion, comes out in December. [Mary Kate Carr]

Pride And Prejudice (2005)
Pride & Prejudice | Completely, Perfectly, Incandescently Happy

Just as the fall signifies the time to return to Mitski’s discography, it also marks the time to rewatch starring Keira Knightley and Matthew Macfadyen. The Jane Austen adaptation is filled to the brim with yearning and affection, expressed in the smallest of moments and gestures. Emotional devastation reaches its peak with Macfadyen’s delivery of the line, “I love you, most ardently.” Emotional devastation is what everyone looks for this time of year, right? [Gabrielle Sanchez]

Little Shop Of Horrors (1986)
Little Shop Of Horrors - Skid Row (Downtown)

On the 23rd day of the month of September, in an early year of a decade not too far beyond our own, a singing, man-eating plant appeared in a flower shop in downtown Manhattan and changed the game. An updated riff on a classic ’60s creature feature, the musical is, in my humble opinion, basically a perfect film, and I can’t stop watching it or talking about it (not that I’ve tried). The subject matter definitely veers toward Halloween, but I tend to watch it on Thanksgiving; what better time for a clever satire of American consumerism and fame-seeking disguised as a B-movie with a killer Motown-inspired soundtrack? [Drew Gillis]

When Harry Met Sally (1989)
When Harry Met Sally... (5/11) Movie CLIP - Sex Dreams (1989) HD

It may not be a fall film per se, but definitely gives off all the cozy vibes I want to feel this time of year. It’s a cinematic hug—warm, familiar, and inviting, like an old friend you see once a year. The scenes that are set in autumn leave a lasting impression, with the jazzy score, seasonal wardrobe pieces, and gorgeous backdrop of Central Park’s colorful foliage. And who better to experience it with than Billy Crystal and Meg Ryan, doing the most with their limitless charm and talent? Not to mention a scene-stealing Carrie Fisher. But I’d be remiss if I didn’t give proper credit to director Rob Reiner and screenwriter Nora Ephron, the real-life Harry and Sally (minus the romantic relationship), for making this unconventional romantic comedy worth returning to, again and again. [Cindy White]

Practical Magic (1998)
Practical Magic (1998) Official Trailer - Sandra Bullock, Nicole Kidman Movie HD

Even if you took the witches out of —which, why would you ever? But for the sake of the hypothetical—you’d still be left with the most dreamy fall movie. The Owens sisters (impeccably dressed and impeccably played by Sandra Bullock and Nicole Kidman) grew up in a town that feels trapped in the amber of autumn, populated by big, old New England manors and flush with fall colors. Now add the witches back in, because they own the season after all! The big magics—the family curse, the misguided resurrection—are perfect Halloween fare. But it’s the smaller, practical magics, like stirring coffee without hands or blowing on a candle wick until it lights, that give the movie its cozy, lived-in feeling. In this movie, love (be it romantic love or the love between sisters) is the true magic. It’s the perfect film to watch while curled up under a blanket on a brisk fall day. [Mary Kate Carr]

Little Women (2019)
Little Women (2019) - Laurie Proposes to Jo Scene (6/10) | Movieclips

I know, I know, Bod Odenkirk’s epic entry in Greta Gerwig’s on Christmas morning may make you think it’s good holiday viewing, which it is, but the film also captures the coziest fall vibes. The credit goes to its autumnal color palette, the scenery, and the outfits. Set in Civil War-era Concord, Massachusetts, the film is an emotional undertaking as it explores the lives of sisters Jo, Amy, Meg, and Beth March. The best way to watch is probably with a cup of—and I’m sorry to say this—pumpkin spiced-something and a warm blanket. [Saloni Gajjar]

Juno (2007)
Juno in the drug store and walking home - Clip 2 of 19 - JUNO film (2007)

begins in the fall when the teenage Juno McGuff gets pregnant, but, famously, pregnancies are nine months, so we follow her for the full term of the pregnancy—which also happens to be the length of Juno’s junior year of high school. Even as the seasons on screen change, Juno always screams fall vibes to me; it’s fundamentally a movie about the loss of innocence and being dragged into a stage of life where the sun sets at 4:30 in the afternoon. Juno’s life changes with the seasons, but it’s a hopeful reminder that spring is just around the corner. Also, there’s just so, so much orange. [Drew Gillis]

Fantastic Mr. Fox (2009)
FANTASTIC MR. FOX - Official Theatrical Trailer

Are you cussing kidding me? We could not have a fall film list without Wes Anderson’s —the first of two Roald Dahl adaptations in this roundup. This film exists entirely within the hues of autumn, with rich oranges and yellows laying the visual groundwork. It’s a comforting and touching adventure about a family of foxes and their woodland creature friends. What’s not to love? [Gabrielle Sanchez]

10 Things I Hate About You (1999)
Patrick sings to Kat - Heath Ledger (10 things i hate about you)

Can this be the fall we finally agree, culturally, that 1999 Joseph Gordon Levitt was the blueprint for today’s Andrew Garfields and Joe Keerys? The high school movie to end all high school movies, the most fun Shakespeare adaptation there is— is touchstone teen cinema with verve, style, and a soundtrack to match. A luminous highlight in the late Heath Ledger’s career, the film is a beautifully goofy ode to the turn of the 21st century—not to mention a star-maker for a young David Krumholtz and Gabrielle Union. Don’t let Allison Janney’s strict, hysterically smut-happy guidance counselor fool you: 10 Things I Hate About You is a bursting heart made manifest. [Hattie Lindert]

Mermaids (1990)
Mermaids Official Trailer #1 - Bob Hoskins Movie (1990) HD

is a quintessential autumn watch as it takes place during the season, featuring the scenic small town of Eastport, Massachusetts. The 1990 film from Richard Benjamin stars Cher, Winona Ryder, and in one of her earliest roles. Together, they’re a dysfunctional family caught up in the whims of matriarch Rachel Flax (Cher), who has them on the move the moment any trouble arises. It’s a film about the strength of bonds between mothers and their daughters, a theme that always becomes more salient as the holiday season nears. [Gabrielle Sanchez]

The Witch (2015)
The Witch | Peek A Boo | Official Clip HD | A24

Chalk it up to New England heritage or a childhood obsession with Roanoke: recaptures my heart every September. Robert Eggers’ 2015 Puritan nightmare made a star, and for good reason—her eerie performance fills up a bleak world at the edge of the woods where the only thing more fearsome than heaven is heresy. The Witch’s most terrifying moments are its subtlest; a peekaboo game gone wrong, or the jarring bleat of a family goat. Eggers’ most recent offering, The Northman, courted a blockbuster-sized audience, but The Witch is a dish best served at home, where I can practice my Olde English accent in peace. [Hattie Lindert]

The Nightmare Before Christmas (1993)
This Is Halloween (From Tim Burton’s “The Nightmare Before Christmas”)

Despite considering myself a beachy person, each year I’m reminded of an inherent affinity for autumn: My birthday (September 30) kicks off spooky season, my favorite movie is , and there are few cinematic icons to whom I relate more than my namesake (okay, not really) Jack Skellington. It’s the kind of masterpiece that rewards annual rewatching, featuring a stop-motion visual feast from the brain of a never-better Tim Burton and eerie, evocative musical numbers from Danny Elfman. I may mourn the end of summer, but when I feel that irresistible chill in the air, an internal monologue echoes Jack’s cathartic epiphany: “That’s right … I am the Pumpkin King!” [Jack Smart]

Clueless (1999)
Clueless (1995) Trailer #1 | Movieclips Classic Trailers

Not putting on our list? Ugh, as if! Alright, with this corny tribute out of the way, let’s talk about how 1995 film isn’t just the best Jane Austen adaptation, but also a perfect fall film. It simply screams ’90s back-to-school thanks to Cher and Dionne’s wardrobe, how it influences their character development, and all the shenanigans that follow when they befriend Tai. Clueless might just make you want to go to high school all over again. [Saloni Gajjar]

Phantom Thread (2017)
PHANTOM THREAD - Official Trailer [HD] - In Select Theaters Christmas

Guided by Johnny Greenwood’s stunning score, Paul Thomas Anderson’s remains a delicate masterpiece that sweeps you away completely. Everything about this film is so detailed, so crisp, and so inviting. and Vicky Krieps are truly enrapturing on screen, in a story about the human desire to feel needed. Phantom Thread serves as a gentle reminder that the levity of summer is over and it’s time for the romanticism and poeticism of fall. [Gabrielle Sanchez]

Matilda (1996)
Matilda (1996) - Little Bitty Pretty One Scene (7/10) | Movieclips

(the best Roald Dahl adaptation) packs an especially emotional punch during the back-to-school season. Sure, the average Joe doesn’t share our titular heroine’s unique gifts. But who wouldn’t connect with the enormity of a new school, the power of a truly great teacher, and the struggle to eke out independence as a small-but-mighty kid? Come for Rhea Perlman and Danny Devito’s gleefully evil parents; stay for the venerable kindness of Embeth Davidtz’ Ms. Honey, who gently reminds me each cuffing season that yes, I’m still queer. Until I can have my own cottage in the woods, I’ll settle for a yearly onscreen visit to hers. [Hattie Lindert]

 
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