Films that feel like fall

Tuesday, October 15, 2019

We're halfway though October and since the weather is just starting to shift, I'm in the mood for cozy fall films in the evenings. I usually gravitate towards the more melancholy, thoughtful, quirky ones--either with sweeping soundtracks or themes of transition and change. These are some of my favorites that I go back to this time of year. 

Dead Poet's Society
Robin Williams, an all-boys private school, poetry in the fall. This film sums up all my feelings and beliefs about liberal education--I have a lot--and is a lovely reminder of all the teachers who impact lives. Spoiler: that being said, there's decidedly no happy ending. 

Moonrise Kingdom
While this story of two children running away takes place on a sunny island, that wistful in-between feeling of summer slipping into fall permeates the film. With all the traditional hallmarks of Wes Anderson--magnificent soundtrack, richly saturated colors, Bill Murray--it's lovely for a rainy day. 

You've Got Mail
Oh, Kathleen Kelly. You, your tweed dresses over black turtlenecks, and love of books are perfect in every way. Nora Ephron is the queen of thoughtful romantic comedies and this reunion of Tom Hanks and Meg Ryan is one of my favorite films, ever. Watch for New York in the fall, two booksellers who hate each other in real life but fall in love online, and a love letter to the '90s.

Dan in Real Life
A widowed father bumps into a delightful woman on the way to a Thanksgiving family reunion...only to arrive and realize she's there as well as his younger brother's girlfriend. Cue impending weekend of awkwardness, conflicted feelings, and navigating family tension as an adult. Funny, tender, and surprisingly emotional. Also, Steve Carell at his charming, wry best. What more do you need?

When Harry Met Sally
You can't go wrong with Meg Ryan in the fall. She's the perfect foil to Billy Crystal's cynical Harry in Rob Reiner's hilarious answer to the question, "Can men and women really be friends?" Second spoiler: they can't. I love how the film tracks Harry and Sally's friendship from the loathe-each-other-at-first-conversation stage to begrudging acquaintances to friends to blurred lines. Equally as notable: Sally's hair (and wardrobe) changes over the years. 

Silver Linings Playbook
Two people, both struggling with loss and mental illness, meet and clash. They form a blunt, heartwarming friendship. Jennifer Lawrence and Bradley Cooper are in top form here. Football, anger, dancing, Hemingway--this has it all. 

The Royal Tenenbaums
Another Wes Anderson masterpiece--this time about dysfunctional families and gifted children who grow up to grapple with failure and loneliness. Strangely sweet, iconic, and deadpan to perfection. The melancholy humor and warm color scheme give this an autumnal feel. 

Lost in Translation
Some films find you, like books, at the time when you most need them. I stumbled upon this gem of a film during one of the loneliest months of my life when several relationships were disintegrating. I would come back to my dorm room on a cold, blustery day--a cocoon of warmth, soft light, safety--to try and sort through what was happening. One weekend I felt so exhausted and vulnerable that all I could do was make a simple to-do list: 
-roast vegetables
-watch Lost in Translation

And cry I did, watching the story of two isolated and lonely strangers who meet in Tokyo, both of them wondering, 'what comes next?' Beautifully artistic, reflective, and gentle. 

Honorable mentions: Rushmore, The Village, Fantastic Mr. Fox. 

What is your favorite fall film?


  1. I watched You've Got Mail after seeing you write about it here, and WOW that's such a great movie! <3

    1. That makes my heart so happy, Gabrielle! Welcome, welcome to the freshly-sharpened bouquet of pencils club.