Film and TV

The Best Movies To Watch This Fall

Us, whenever the first fall leaf drops.
Us, whenever the first fall leaf drops. Matthew Henry/Unsplash
It’s September, which means it’s time to part ways with the long, hot summer, unpack your sweaters and take a deep breath of cool autumn air. Always a festive season, there are myriad ways to get into the fall spirit: baking pumpkin pies, picking apples, drinking seasonal beers, cool afternoon walks and, of course, watching movies.

These are films with particularly strong autumnal vibes, typically best experienced on the couch with a blanket and your favorite warm beverage. So open some windows, turn on the kettle and celebrate the season with our picks for the best fall films:

When Harry Met Sally (1989)
Amazon Prime

The poster alone for this classic romantic comedy is enough to get you ready for fall; in it we see Harry (Billy Crystal) and Sally (Meg Ryan) conversing in a park on an autumn afternoon, surrounded by lush foliage. The image is so iconic and inviting that someone on Twitter once jokingly mentioned that When Harry Met Sally invented autumn. In the film, Harry and Sally meet in 1977 and then navigate a rocky, hilarious 12-year relationship that constantly teeters between friendship and romance. With an ambitious screenplay by Nora Ephron, the film manages to deftly interrogate the nature of male/female relationships, with a coda as heartwarming as your coffee by the fire on a cool morning.

The Meyerowitz Stories (2017)

Writer/director Noah Baumbach has become a master at dissecting complex family relationships through equal parts pain, humor and pathos. His 2017 film The Meyerowitz Stories follows half-brothers Danny (Adam Sandler) and Matthew (Ben Stiller) as they make sense of their complicated relationship and how it’s tethered to their narcissistic, aloof art professor dad, played by Dustin Hoffman. In previous films, Baumbach’s abrasive humor and piercing honesty seemed almost too cold; here he balances it perfectly with earnest emotion. The movie’s also set during fall and includes a great scene in a country house in the autumnal New York woods.

Mystic Pizza (1988)
Amazon Prime

New England is particularly famous for its fall weather, and one of the best films to use the region during autumn is the classic 1988 romantic comedy Mystic Pizza. Shot on location in idyllic Mystic, Connecticut, it tells the story of three young waitresses employed at the titular pizza joint as they graduate high school and face the endlessly complicated and contradictory dramas of adulthood. It’s both a romantic comedy and an urban drama with a great sense of place. The youthful cast is also excellent, particularly a young Julia Roberts and Lili Taylor, who lend the film a sense of infectious charm and zappy energy. There’s not much of a plot here; Mystic Pizza’s simply a great hangout movie, full of great sweaters, chilly weather, laughs and heart.

Fantastic Mr. Fox (2009)
Disney +

Wes Anderson’s 2009 adaptation of Roald Dahl’s classic children’s novel is about as autumnal as movies can get. From its fall setting and use of apple cider as a major plot point, to its homemade, orange and brown aesthetic and Mr. Fox’s brown corduroy suit, it truly feels made for this time of year. Though it’s a family film, Fantastic Mr. Fox is every bit as eccentric and thoughtful as Anderson’s live-action adult-oriented work. The plot is precise and lively, but really Anderson’s interest lies in family, responsibility, fatherhood and how to live the best life if you happen to be a fox.

Silver Linings Playbook (2012)

Silver Linings Playbook, adapted from Matthew Quick’s 2008 novel, is both an excellent modern take on the screwball comedy and a succinct portrait of trauma and mental illness. It’s also just a deeply endearing movie in the way it openly confronts these issues while possessing a loving and generous spirit toward all its characters. Also central to the warmth of the film is its location: Director David O’Russell swapped the book’s setting of New Jersey for the suburbs of Philadelphia, full of old streets and folk Victorian architecture. This, combined with plenty of foliage, rainy pavement, family dinners and football games means now is the perfect time to revisit this infinitely likable comedy.

Good Will Hunting (1997)

Before they became two of the biggest movie stars on the planet, Matt Damon and Ben Affleck were a couple of young actors from Massachusetts who used their knowledge of blue-collar Boston life to craft the script for Good Will Hunting. The film is about a Massachusetts Institute of Technology janitor named Will Hunting (played by Damon) who happens to be a mathematical genius. After Hunting is arrested for attacking a cop, an MIT professor (Stellan Skarsgard) agrees to help him if he agrees to study mathematics and see a therapist (Robin Williams). There are plenty of fall-set films about education. Good Will Hunting, with its great performances and a script that’s both street-smart and book-smart, is surely one of the best.

You’ve Got Mail (1998)
Amazon Prime
Reunite Tom Hanks and Meg Ryan (previously together in Sleepless in Seattle and Joe Versus the Volcano) for an autumn-set love story in Manhattan rife with sweaters and bookstores, and you might just have the perfect fall movie. The film wears its nostalgia on its sleeve: It’s a paean not just to cozy independent bookstores, but to a screwball comedy tradition dating back to the 1930s and '40s (the film’s actually a loose remake of the 1940 classic The Shop Around the Corner) wherein people navigate a modern, industrial maze and somehow find true love waiting at the end of it. Arguably a triumph for writer/director Nora Ephron, You’ve Got Mail is meant to make you feel good and succeeds in spades.

Dan in Real Life (2007)
Amazon Prime

In Dan in Real Life, Steve Carrell stars as a struggling writer and single parent who visits his parents’ house for an annual family reunion. Directed by Peter Hedges, the film’s a modest character study and also a pleasant — if slightly idealized — portrait of an extended family packed in a house for a weekend. Dan in Real Life may be too sentimental for its own good, but with excellent turns from Steve Carrell and the great Juliette Binoche, plus an irresistible autumnal setting, it’s well worth your time on a chilly fall night.
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