Autumn is my favorite season, and amid pumpkin-flavored everything and cold mornings, I thought I would share 10 films that I feel capture the spirit of the season. Rushmore (1998)
Set during a fall Semester of a school year, Rushmore perfectly captures the feeling of transition. Even though spring is usually the end of the school year, Anderson chooses to set the film from September to December, which fits better thematically with the film's theme of endings and renewal by pain. Wes Anderson's first major film is still one of his best, and perfectly captures the bittersweet feeling of the season.
Dead Poets Society (1989)
Another classic back to school film set at a prestigious boys' school, Dead Poets Society is all about "carpe diem" and seeing things from new angles. It's exactly what education is supposed to be about, and of course at the center of it is Robin Williams' warm and hearty performance as John Keating.
I know all of the Zach Braff and Manic Pixie Dream Girl backlash, but it's 10 years later and I still have a huge crush on Natalie Portman, listen to The Shins, and wanted to be super cheesy and end this description with an ellipsis...
Good Will Hunting (1997)
Autumn is quintessentially New England, of course, and Good Will Hunting is a great Boston movie. Again, the theme of loss and acceptance runs throughout the film, as is the norm for fall media. But the beauty of the film is that it is about learning to confront these things head on, rather then avoiding or wallowing in our losses.
The Last Waltz (1978)
I generally find concert films to be boring unless they are one of my absolute favorite artists, but Scorsese's film may be the high point of the form. Well-shot, and full of special guests, it really does feel like an event bigger than the concert itself. Shot on Thanksgiving, they even rotoscoped out the cocaine from Neil Young's nose, making it still a family-friendly experience.
Hannah and Her Sisters (1986)
There are a slew of autumnal Woody Allen films, but I wanted to include just one, so it had to be Hannah and Her Sisters. The film takes place over the course of 24 months, with Thanksgiving sort of creating a tentpole structure to the film. It may be odd to talk about scale in the context of Allen's filmography, but he captures dysfunctional family better than anyone else in this film, which is both poignant and very funny.
Planes, Trains and Automobiles (1987)
Like the other films on this list that are ostensibly comedies, John Hughes explores a variety of tones in Planes, Trains and Automobiles. Set in the run-up to Thanksgiving, the series of misadventures that take you through life on the way to the place you're meant to be is a definite microcosm for the human experience. But it's also one of the best films for both Steve Martin and John Candy, so it's also wildly entertaining. Just watch where you put your hands.
I didn't want to overburden this list with Halloween films, but I would be remiss not to mention the most essential modern horror film of all time. Scary, but not gory, relentless and innovative, so much has been written about this film that it would be tough for me to capture the breadth of what makes this such a landmark experience. Or you could just go and watch it (again).
Alexander Payne's breakout film is of course a portrait of Midwest life, as told through the golden girl high school senior, Tracy Flick (Reese Witherspoon), and an emasculated teacher Jim McAllister (Mathew Broderick). A smart satire of high school, suburbia, and 90's politics, the film is manages to balance all three of these subjects equally, while creating fully realized characters.
The War Room (1993)
As a political junkie, fall means election season, and no film gets me psyched for delivering campaign literature door to door or putting up signs in the middle of the night like The War Room. James Carville and George Stephanopoulos are both charismatic and charming, and the documentary filmmakers couldn't have lucked out more with the '92 Clinton campaign. It was a roller coaster of a campaign with more ups and downs than any in recent memory, and seeing it all unfold from campaign headquarters is riveting.