Everyone is familiar with the typical spooky season watchlists consisting of films like Hocus Pocus and Jennifer’s Body, but not enough consider the following drama masterpieces as yearly must-sees. Here is a short list of cinematic classics that will provide the most comforting and spectacular fall vibes. 

Gus Van Sant’s Good Will Hunting (1997)

Matt Damon and Ben Affleck’s screenwriting debut showcased in “Good Will Hunting” is all impressive, gritty, and insanely moving. The film follows the small life of a dirt-poor genius, Will Hunting (Damon), living in seedy South Boston with his street-native confidants. When Will is unwillingly recognized for his brilliance amidst his illegal mischief, he is offered access to a world of high status and opportunity. The movie’s ultimate question becomes; will Will continue to deny himself his innate gifts or give himself his best chance by pursuing the higher-quality life he owes himself to pursue? The coming-of-age story is fueled by Will’s palpable angst and trauma accompanied by a spunky love interest, witty humor, and several lengthy philosophical monologues performed by the late and incredibly talented Robin Williams, Will’s therapist. Chug some icy apple cider, take a peak at autumn in New England, and witness a lost twenty-year-old’s inspiring journey of ultimate forgiveness, true friendship, and self-realization. 

David O’Russell’s Silver Lining’s Playbook (2012) 

Silver Lining’s Playbook is an edgy, off-beat drama/romantic comedy graced by the unique performances of Bradley Cooper, Jennifer Lawrence, and Robert DeNiro. This film captures the honest struggles of mental illness while melting the hearts of all viewers through its central unconventional love story. The 2012 O’Russell indie flick features entertainingly obsessive Eagles fandom and superb comedic relief swiftly delivered by all cast members. If it is me reading the signs, this film is a holiday movie at its heart, with Pat (Cooper) and Tiffany’s (Lawrence) first date taking place on Halloween night and the final scene filmed under street Christmas lights. The tear-jerking closing moments reveal the story’s key message that there is hope in unfortunate circumstances. This two-hour and two-minute film is best served with a slice of pumpkin pie and a steaming cup of cinnamon coffee (or perhaps Raisin Bran and tea :))

Rob Reiner’s When Harry Met Sally (1989)

As far as romantic comedies go, When Harry Met Sally, starring Billy Crystal and Meg Ryan, is the ultimate go-to with its charming banter and proverbial, ultimately not-so-platonic male/female friendship. The film does more than showcase Harry Burns’s impeccable fall style with his glorious chunky sweaters and trendy leather bomber jackets. It loudly and brutally honestly discusses the sticky themes of exploring life and love in one’s late twenties. Harry and Sally’s provocative dynamic creates a satisfying contrast of character that allows for intriguing conversation and relatable controversy expressed through stereotypical male and female perspectives. It offers insight into the feelings following heartbreak and, perhaps most of all, brings to light the questions and concerns of the singledom of the everyman. It is bold, it is unique, and it is the movie to watch while sipping tomato soup and munching on grilled cheese sandwiches. What better way to spend a crisp October night than to cuddle up on the couch and spend an hour and thirty-six minutes feasting your eyes on New York’s spectacular foliage and living vicariously through the sporadic and continuous montage of real-life couple’s origin stories?

Add these quirky and personable fall films to your watchlist for some melancholic tunes and introspective thought!