I bid farewell to the tan that I worked hard for – hours spent by the lake sans sunscreen – and welcome autumn. This list goes out to my old roommate Hannah, with whom I spent chilly Wisconsin evenings watching these exact movies. Expect any combination of the following: witches, wool sweaters, romance, a boarding/catholic school, orange trees, and the East Coast.
- The Craft (1996)
Sarah Bailey (Robin Tunney) is the new girl at a SoCal Catholic school and finds a place as the fourth witch in a small group. Who knew San Francisco could get so stormy. They visit the local occult shop where Lirio (Assumpta Serna), a Spanish witch, offers them guidance, which Nancy (Fairuza Balk) most often goes against. This group of friends tackles high school’s ups and downs, mental illness, parental struggles, and the irreversible power of some spells. The soundtrack and costumes are top-tier.
- Practical Magic (1998)
Based on Alice Hoffman’s 1995 novel, this film follows two sisters (Sandra Bullock and Nicole Kidman) born into a family of witches. They live in a beautiful Massachusetts house with their witch aunts, who raised them after their parents’ death. As each man whom they fall in love with falls to their death, the sisters navigate relationships and a murder accusation. It seems that true love and sisterhood are stronger than any curse. The soundtrack is great, and a sequel is set to be released on September 18, 2026.
- Good Will Hunting (1997)
After a fist fight involving the police, MIT Professor Lambeau (Stellan Skarsgård) agrees to help Will (Matt Damon) avoid jail time if he studies mathematics with him, and attends therapy sessions with his old friend, Dr. Sean Macguire (Robin Williams). William’s performance will make you chuckle and sob as he tries, and at times succeeds, to peel the layers of Will’s psyche. Much to my delight, a great deal of the soundtrack is Elliott Smith’s music.
- Dead Poets Society (1989)
I remember watching this film with my own English teacher in middle school and crying at my little desk. Robin Williams provides guidance yet again, but this time as John Keating, an English teacher at Welton Academy, an all-boys boarding school. Reviving Keating’s secret poetry club, to the parents’ and the school’s dismay, the young men create a brotherhood, learning to love language and the passion and courage that it unleashes in them.
- Fantastic Mr. Fox (2009)
Ah, a quintessential autumn movie, based on Roald Dahl’s children’s book. This is a very orange watch, and I adore Wes Anderson’s stop-motion, which reminds me so much of a childhood classic in my home, Chicken Run (though perhaps the orange animals trespassing factory farms contributes to that association). George Clooney and Meryl Streep voice Mr. and Mrs. Fox, and I always feel the entire cast had such a great time making this film.
- Little Women (2019)
Greta Gerwig’s was the seventh adaptation of Louise May Alcott’s 1868 novel, in which four sisters (Saoirse Ronan, Florence Pugh, Emma Watson, Eliza Scanlen) live with their mother Marmee (Laura Dern) in Concord, Massachusetts. Three of them had been away from home, pursuing their dreams, but they reconvene when Beth falls ill. Navigating poverty, love, passion, a father fighting in the Civil War, Jo (Ronan), a dedicated writer, works on her magnum opus – the story of these very women.
- Death Becomes Her (1992)
Madeline Ashton (Meryl Streep), a beautiful actress with a dwindling career, meets her friend Helen’s (Goldie Hawn) plastic surgeon fiancé, who immediately falls for her instead. Madeline achieves eternal youth and beauty (as if Streep is capable of aging), but at a cost. Helen and Madeline fight, through procedures and a curious elixir, to be the most attractive and youthful. This movie is totally weird, and the special effects are comical (backwards heads and double jointed everything) – I love it.
- Mona Lisa Smile (2003)
Not to be reductive or binary, but this is the girl version of Dead Poets Society. Julia Roberts plays a freshly graduated art history professor at the all-girls Wellesley College, who opens the minds and hearts of her students, challenging their views on women’s role in society. I enjoy this film for the vintage outfits (trench coats and matching hats, oh my!), early 2000’s actresses (Kirsten Dunst and Julia Stiles) playing 1950s college students, and the marvelous Massachusetts campus in all its leafy glory.
- Eternal Sunshine of the Spotless Mind (2004)
Something about the East Coast just screams fall. I was quite lost when I first watched this, as we travel through time and memory, but I understood better after a second watch (pay close attention to Clementine’s (Kate Winslet) changing hair color. Joel (Jim Carrey), an introvert, and Clementine, a manic pixie dream girl, meet on a train back from Montauk, and slowly discover that they have met before, and had erased each-other from their memory. Despite the pain caused by the roller-coaster of all relationships, this film has such heartwarming moments that prove that true love is worth the risk of loss.
- When Harry Met Sally (1989)
In case you missed it: Harry (Billy Crystal) and Sally (Meg Ryan) graduate from the University of Chicago and carpool together to New York, arguing about whether men and women can really be friends. Not planning on seeing each-other again, chance encounters in the Big Apple go to show that sometimes, all that you’re looking for in love is standing right in front of you. Sweaters, yellow trees in Central Park, and apple pie à la mode render this a classic autumn flick.
