Movies to watch this autumn

I love When Harry Met Sally. And not just because of their chunky knit jumpers.
Photo courtesy of Columbia Pictures/Everett Collection

Two years ago, I wrote something I’m immensely proud of. It was in the Notes section of my phone. And it was an autumn movie list.

The criteria? Anything with fall foliage, heartwarming fuzziness or supernatural spookiness.

I love immersing myself in a new season and planning things to look forward to. And autumn? Well, that’s the best one! Delicious drinks, cosy clothing, fresh stationary for back to school. New shoes. Cool hats. There’s Halloween, fireworks, the lead-up to Christmas. And the world is finally the perfect temperature.

My movie list is just the cherry on top.

Back in 2017, my sister and I worked our way through the list and loved it. I told my friends about it – they all wanted a copy too! So, I’ve gone one better. It’s now a blog post so anyone can join in.

Just grab a blanket, snap the gingerbread and pour yourself a nice warm drink. Let’s get started:

Practical Magic

The Owen sisters, Sally and Gillian, are witches. And very, very different. But they must come together to overcome life’s obstacles and put an end to the family curse haunting them.

This has everything to satisfy my autumnal urges – and more. There’s witchcraft, strong women, nineties style, Sandra Bullock, Nicole Kidman, nail-biting suspense and a truly satisfying ending. Plus the iconic ‘MIDNIGHT MARGARITAS’ scene.

If you like Halloween but not horror films, this is one to watch this October.

When Harry Met Sally

‘Men and women can’t be friends because the sex part always gets in the way,’ Harry tells Sally at the beginning of the film. Despite this, their friendship blossoms and the film follows their intertwining lives throughout their 20s and 30s.

Written by my personal hero Nora Ephron, every line in this movie manages to be pithy, cynical, hilarious and warm – all at once.

This is one of my favourite films, so I’ll happily watch it all year round. But the shots of a beautiful orange-tinged Central Park firmly and its cosy jazz soundtrack place this into the autumn category for me. You can see the fast-paced banter, gorgeous foliage and some spectacular outfits in this clip:

Good Will Hunting

Will Hunting is working as a janitor at MIT when a professor realises he’s a mathematical genius. (We’ve all seen the ‘solving the impossible equation on the blackboard’ scene spoofed before!)

But Will is a bit of a delinquent and doesn’t really have any interest in academia. He needs help from a therapist (Robin Williams) to confront his demons, address his past and choose his future.

This film will warm – and break – your heart. A bittersweet movie for an autumn evening. And the Boston backdrop (set during the autumn, as you can see below) will have you reaching for a cable-knit cardigan in no time.

You’ve Got Mail

Kathleen Kelly owns a cute children’s bookshop. Until a chain discount bookstore opens around the corner, threatening to put her out of business. And the owner, Joe Fox? He’s driven, ruthless and a real jackass.

But what Kathleen doesn’t know is, she’s been chatting to him on a chatroom. Totally oblivious to his real identity.

The first part of this movie is pure autumnal dreaminess. It begin with a monologue about New York in the fall and includes the immortal line: ‘If I knew where you lived, I’d send you a bouquet of freshly sharpened pencils.’ Swoon. This always gets me in the mood for September.

The Addams Family

Con-artists try to deceive the eccentric Addams family using an accomplice who claims to be their long-lost Uncle Fester. Fiendish fun ensues.

My question is: If autumn isn’t the perfect time to watch this, when?

(See also: Addams Family Values.)

Dead Poet’s Society

Robin Williams plays an English teacher starting a job at a very traditional boys’ school. He’s unorthodox and challenges the privileged kids. Which, as you might imagine, doesn’t go over well. But he’s the inspirational teacher you always wished you’d had.

Yes, this movie breaks my heart a little because I miss Robin Williams terribly (and the storyline has its fair share of tragedy). But he is just marvellous in this serious role. It belongs in my autumn list because it begins in September, in an East coast school, surrounded by the autumn leaves I so love.

Hocus Pocus

When teenager Max moves to Salem, he struggles to fit in at his new school. He’s not having a great time. And then he awakes a trio of diabolical witches who were executed in the 17th century. Oops. 

This is the ultimate Halloween film, as I can’t deal with anything too scary (I promise I won’t put too many in this list). Plus, Bette Midler, Kathy Najimy and Sarah Jessica Parker make the perfect witches. It’s a classic.

Edward Scissorhands

A creepy scientist (Vincent Prince, naturally) builds a human – but dies before he can finish the hands. Thus, adorable, scissor-handed Edward mopes around his abandoned castle/factory until a nice Avon lady stumbles upon him.

This film is one of Tim Burton’s sweeter works, but it’s still wonderfully strange and whimsical. Perfect for October watching. See also: Beetlejuice.

Mona Lisa Smile

Katherine Watson (Julia Roberts) is hired to teach art history at the prestigious all-female Wellesley College in 1953. Determined to confront the outdated customs, Katherine inspires her traditional students to challenge the lives they are expected to lead.

It’s not just a powerful film that forces you to look at choice within feminism and how the expectations for women have changed in the last 50 years. It’s also aesthetically delicious. 1950s outfits. Rich tones. A gorgeous New England backdrop for a new school year? It’s guaranteed to get you feeling the autumn fuzzies.

Side note: There’s a scene between Maggie Gyllenhaal and Kirsten Dunst (you’ll know when you see it) which really gets me, it’s so beautifully acted. And the ending always makes me cry, in a good way.

Argh, you’ll love this.

Little Women

Based on Louisa May Alcott’s classic novel, Little Women is the story of four very different sisters growing up in the 1800s. (I hope Rachel and Joey from Friends haven’t given you too many spoilers.)

It’s not an autumn list without and period piece, and this one is scattered with snow, thick cloaks and reading by candlelight. I’d pair it with a blanket and a hot chocolate during a chilly November afternoon.

Fantastic Mr Fox

What says autumn more than the triumphs and perils of a stop-motion fox family? If you don’t know the story, it’s about an arrogant fox who steals food from three vengeful farmers – and naturally, chaos ensues.

The genuinely funny script, gorgeous animation, and vocal talents of Meryl Streep, George Clooney, Owen Wilson (et al) propel this from being a cutesy kids film to a genuinely enjoyable watch.

Plus, the movie’s lush, rich colour palette – what else do you expect from Wes Anderson? – perfectly complement an autumnal Sunday afternoon.

The Princess Bride

This bizarre, lovely, silly cult-classic had to make the cut. It’s a fairytale adventure, which, I don’t know, just feels quite autumnal to me?

It’s a story of true love, with pirates, giants, poison, swordsmen, vendettas, certain death, magic, princes and princesses and, erm, rodents of unusual size. What more could you want? The cast is phenomenal too, featuring the talents of Billy Crystal, Carol Kane and Peter Cook in really fun cameos.

I didn’t discover this movie until quite late in life – if you haven’t seen it yet, settle down one afternoon and prepare to understand a lot of references and quotes which have been going over your head for decades.

‘As you wiiiiiiiiiiiiish.’

Here’s a downloadable PDF, in case you want to save it!

If you’ve completed the list and want even more seasonal movies, try: Nightmare Before Christmas, Beetlejuice, Corpse Bride, any of the Harry Potter films, The Craft and Sleepy Hollow.

Have I missed anything? Let me know what your favourite fall film is.

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