You Should Fall in Love With These Classic Movies This Autumn

The best films to celebrate the season's vibe.

By Brenden Gallagher

Fall is here. The leaves are changing. Sweaters are making their way out of your closet and out in the streets. All of a sudden staying indoors is starting to look a lot more appealing. As that crisp air turns you into a couch potato, let’s celebrate the arrival of autumn with some of the best movies set in the fall. From melancholic reflection on past romances to melancholic reflection on past friendships, Fall movies have it all.

  • Dead Poets Society

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    You get nostalgic just thinking about Dead Poet’s Society. You’ve got autumn leaves, sweaters, inspiring teachers and coming of age. Watching the film about an English teacher (Robin Williams) who teaches a class of teenage boys to think for themselves has almost the same effect as cracking that dusty old high school yearbook. Everyone has the one teacher they credit with making them the person they are today. Dead Poet’s Society perfectly captures the feeling of watching your worldview open up before your eyes.

  • When Harry Met Sally

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    As Dead Poet’s Society causes an OD on high school nostalgia, When Harry Met Sally is sure to make you nostalgia for past romances. The film follows Harry (Billy Crystal) and Sally (Meg Ryan) at five year intervals as the continue to make excuses not to be together. As we jump through time, we follow their evolving notions on all of the factors that swirl around dating. Can men and women be friends? How important are children and marriage? What does it mean to be with someone and what does it mean to be alone? Though the film is fast approaching its thirtieth birthday, it is surprisingly current. It might just turn out that the film is timeless

  • Good Will Hunting

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    If you’ve moved a greatest distance from your hometown or have a friend who has, we dare you to watch that scene without your eyes watering up. Another sentimental film about a sentimental education, this film stars Matt Damon and Ben Affleck before they were Hollywood glory boys. Good Will Hunting tells the tale of a janitor who turns out to be a whiz kid and his best friend who just wants to be left behind.

  • Planes, Trains, and Automobiles

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    No film better depicts the agony and the ecstasy (mostly agony) of getting home for the holidays like Planes, Trains, and Automobiles. This movie features John Candy and Steve Martin at the top of their comic game, directed by John Hughes at the height of his powers. Planes, Trains, and Automobiles is alternately hilarious and heartwarming, setting the standard for “home for the holidays” movies for decades to come.

  • Hannah and Her Sisters

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    A less jovial Thanksgiving movie than Planes, Trains, and Automobiles, Hannah and Her Sisters tells the story of, you guessed it, Hannah and her sisters, through three successive Thanksgivings. The film delves into the dynamics between the sisters as they navigate their sex lives, careers, and search for personal fulfillment. We see how competition, jealousy, love, and various other emotions come together to form a family dynamic as each sister searches for contentment in their own way.

  • Days of Heaven

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    Terrence Malick’s notoriously long production process was further extended for this film, which was primarily shot at magic hour, the short period of time just before sunset known for perfect lighting. This romantic drama that takes place on Texas farm land premiered to mixed reviews but has since come to be known as one of the best films of the twentieth century, largely thanks to the breathtaking photography.

  • Far From Heaven

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    This 2002 film by Todd Haynes pays tribute to cinematic style of Douglas Sirk. Sirk’s melodramas were known to be visually rich and emotional complicated, and that is certainly true here. The film follows husband and wife Cathy and Frank Whitaker (Julianne Moore and Dennis Quaid) as these 1950s suburbanites explore forbidden loves. For Frank, it is same sex relationships, and for Cathy it is the love of a Black man (played by Dennis Haysbert).

  • October Sky

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    In the coal country of West Virginia, many people never even imagine a life outside the mines. When they do get a chance to escape, it usually comes by way of an athletic scholarship. To say that Homer Hickam’s (Jake Gyllenhaal) dream of building and designing rockets is strange to his neighbors is an understatement. October Sky follows Homer as he chases his dream and tries to convince his father (Chris Cooper) that his dreams are worth chasing.

  • Hocus Pocus

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    There aren’t many Halloween movies that aren’t slashers or kids movies. Hocus Pocus is one of few Halloween films that aims for laughs instead of screams, and aims to please adults and children alike. Anchored by unforgettable performances from Bette Midler, Kathy Najimy, and Sarah Jessica Parker, this film remains a cult classic because of its light take on our spookiest time of the year.

  • Fly Away Home

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    This sweet family drama follows a young girl’s quest to teach a gaggle of goslings how to migrate. Amy (Anna Paquin) happens upon some goose eggs, and when the goslings hatch they “imprint” on her as their mother. With the help of her inventive father (Jeff Daniels), Amy finds ways to care for the geese and get them South for the winter.

  • Hero

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    One of the most visually stunning action movies of all time, Hero was an international success for Chinese director Zhang Yimou. The beautiful fight choreography is supplemented by the luscious colorful visuals that provide the film’s background. The varied color palate supports the storytelling that offers three different perspectives on the same series of events, as a web of intrigue surrounding an assassination plot unravels.