The 25 best movies to mark the fall season
Cosy and comforting classics ahead.
Fall marks a time where we often rewatch formative films that evoke the best of cosy season. Some of the best romantic comedies (like Practical Magic and Brown Sugar) and sweeping dramas (Good Will Hunting and Dead Poets Society, anyone?) serve as the ultimate comfort watches while cuddled up on our couches with a hot toddy or warm cider in hand.
Ahead, we've rounded up some of our favourite fall watches to mark the season, including timeless classics like Hocus Pocus, Little Women, Knives Out and more. And if you're in need of more seasonal inspiration? Our definitive lists of the best Halloween movies, 90s movies, and 2000s rom-coms are here for you.
Good Will Hunting (1997)
Will Hunting (Matt Damon) is a young man from South Boston who works as a janitor at MIT. One day, he is caught solving a graduate-level math problem on the classroom blackboard of Professor Gerald Lambeau (Stellan Skarsgård). Seeing Will’s genius-level IQ and wanting to nourish his potential, Lambeau tracks Hunting down (at a jail sentencing for attacking a police officer) and then makes a deal with the court to place Will under his personal supervision and to see a therapist, Sean Maguire (Robin Williams, in one of his best performances). Their sessions become more than therapy; they spur an unlikely supportive friendship that they both ultimately didn't know they needed. The 1997 film kickstarted what would soon become a lustrous creative partnership between Damon and his friend and co-star, Ben Affleck, who both took home the Oscar for Best Original Screenplay later that year.
Brown Sugar (2002)
Syd Shaw (Sanaa Lathan), is the editor in chief of hip-hop magazine XXL, and slowly and reluctantly realises she is in love with her childhood friend Dre Ellis (Taye Diggs), a recording executive. They are both bosses in the music industry, sharing a passion for the artistry and the culture, but though completely compatible, they are both reticent about expressing their true feelings for each other. Lathan and Digg's on-screen chemistry in this early aughts classic is undeniable.
Baby Boom (1987)
J.C. Wiatt (Diane Keaton) is a management consultant in New York, a workaholic who clocks 80 hours a week, her career the central focus of her identity. But her outlook changes when she is left with a baby girl, Elizabeth, from a distant relative who recently passed away. J.C. decides to leave the corporate world behind and move to an estate in Vermont, where she tries her best to assimilate to country life and learns a lot about motherhood.
Far From Heaven (2002)
Cathy Whitaker (Julianne Moore) is a privileged woman in 1950s Connecticut, the model housewife who does everything by the proverbial book. But under her prim exterior, her marriage is in crisis: Her husband has an affair with a man, setting the rumour mill spinning in their conservative community. Cathy strikes up a friendship with the son of her former gardener (Dennis Haysbert), leading to mounting racial tensions that ostracise her further still.
Dead Poets Society (1989)
John Keating (Robin Williams) is a new teacher at an all-boys boarding school in Vermont. The institution is known for its high standards and sticking to antiquated customs, which places huge pressures on the student body. Using unconventional teaching methods that strike an emotional chord with his class, Keating helps alleviate that stress by encouraging his students to break free from tradition and pursue their dreams—leading to joy and tragedy.
Fly Away Home (1996)
Amy Alden (Anna Paquin) is a teenager who moves to Canada to live with her father (Jeff Daniels), a wacky inventor, after losing her mother in a car accident. She is understandably unhappy in her new surroundings, until she discovers a nest of goose eggs behind her house. After they hatch, she becomes a mother figure to the goslings and finds a new purpose: to teach them how to fly south before winter.
Hocus Pocus (1993)
In 17th-century Salem, Massachusetts, the Sanderson sisters (Bette Midler, Sarah Jessica Parker, and Kathy Najimy)—three witches, each with their own unique abilities, capture a young girl—draining her life to regain their youth. They are caught by the townspeople and hanged for their crime, but before they meet their end, they vow to return and wreak havoc. Three hundred years later, teenager Max Dennison (Omri Katz), his sister (Thora Birch), and his love interest (Vinessa Shaw) accidentally bring back the coven on Halloween night. We dare you to name a better Halloween film.
Homeward Bound: The Incredible Journey (1993)
The three Seaver children are devoted pet owners, doting over their two dogs and cat: Shadow, an aging retriever (Don Ameche); Chance, a young bulldog (Michael J. Fox); and Sassy, a Himalayan. And in return, these animals love them. So much so that when the family goes for a vacation to San Francisco, leaving their pets at a ranch, the animals feel abandoned and journey through the American wilderness to reunite with their owners.
If Beale Street Could Talk (2018)
Tish Rivers (KiKi Lane) and sculptor Fonny Hunt (Stephan James) are a couple in 1970s Harlem, both deeply in love with one another since childhood. As young Black adults, they plan for a bright future while trying to overcome society’s prejudice. But their life together is shattered when Fonny is incarcerated, for a crime he did not commit.
Little Women (2019)
Adapted from Louisa May Alcott’s classic novel of the same name, Little Women is about the March sisters (Jo, Meg, Amy, and Beth) as they grow up in rural 19th-century Massachusetts. With their father away during the Civil War, the girls and their mother have to overcome poverty and the societal restrictions placed upon women. Each sister has her own distinct personality and her own goals, but the four are forever bonded by their love for one another.
Knives Out (2019)
After his 85th birthday party, wealthy crime novelist Harlan Thrombey (Christopher Plummer) is found dead at his sprawling country estate, overrun by a group of family members who each has a motive for wanting to murder the patriarch. Investigating the case is the suave and astute detective Benoit Blanc (Daniel Craig), who calmly and wittily tries to uncover the truth against an atmosphere of lies and duplicity.
Love and Basketball (2000)
Monica Wright (Sanaa Lathan) is passionate about basketball, her drive propelling her to the big leagues. She is childhood friends with Quincy McCall (Omar Epps), who also loves the sport and has the same competitive spirit, but is stifled by the large shadow cast by his father (Dennis Haysbert), a professional player for the Los Angeles Clippers. As the years pass, Monica and Quincy’s feelings for each other grow stronger and stronger, but their careers keep pulling them apart.
Mona Lisa Smile (2003)
The year is 1953 and Katherine Watson (Julia Roberts) is a free-spirited scholar who recently received her graduate degree from UCLA. She accepts a position as an art history professor at Wellesley College, an all-female institution with strict moral codes, but Katherine sees the potential in her students and, much to the chagrin of the higher-ups, encourages her students to think bigger and more broadly. It's Julia Roberts at her best.
October Sky (1999)
Homer Hickam (Jake Gyllenhaal) and his brother Jim (Scott Miles) are the sons of a coal miner in West Virginia. Their father John (Chris Cooper) expects them both to follow in his footsteps, but things change when Homer is inspired by Sputnik, the first artificial satellite, going into orbit. With help from friends and his high school teacher (Laura Dern), Homer starts building rockets in the hopes of competing in the national science fair, which offers a college scholarship as the prize. Based on a remarkable true story, October Sky will absolutely pull at your heartstrings.
One True Thing (1998)
Ellen Gulden (Renée Zellweger) is a journalist in New York, a career inspired by her father (William Hurt), a novelist and English professor, whom she idolises. Her mother (Meryl Streep), a plucky housewife, is diagnosed with cancer, and Ellen is guilted by her father to return home, take care of her mother, and fill the older woman’s shoes. Soon enough, she sees all the sacrifices her mother has made to keep their family together.
Planes, Trains and Automobiles (1987)
Neal Page (Steve Martin) is an advertising executive who’s just finished a business trip to New York City, and is now trying desperately to return to his family in time for Thanksgiving. Along the way, he joins forces with Del Griffith (John Candy), his hapless polar opposite. Together, they navigate torrential weather and a whole lot more to get home to Chicago.
Practical Magic (1998)
Sally Owens (Sandra Bullock) is a witch in a small town in Massachusetts, who abandoned magic to raise a normal family and escape the stigma that comes with it. When she is widowed with two girls after her husband dies of a curse, she is forced to move in with her wacky aunts. At the urging of her daughter, Sally pushes through her sadness and opens a store that sells high-end bath and beauty products. And when her rebellious sister Gillian (Nicole Kidman) gets into supernatural trouble with a boyfriend, Sally has to take up the family craft again.
Rudy (1993)
Rudy Ruettiger (Sean Astin) is a steel-mill worker in Joliet, Illinois, who has always dreamt of attending the University of Notre Dame and playing for its football team. The problem is, he doesn’t have the grades, skills, or funds to attend the institution. But after his best friend is killed in an explosion at the mill, Rudy makes it his mission to become one of the fabled Fighting Irish in this much-loved tearjerker.
School of Rock (2003)
Dewey Finn (Jack Black) is a struggling guitarist who gets thrown out of his band. In need of work, he pretends to be his friend and roommate, a substitute teacher, and takes a gig at a private elementary school. Seeing the talent in his students, Dewey instructs them in all things rock ’n’ roll, eventually forming a band and enlisting them in a local music competition to win $20,000 in prize money.
Sweet Home Alabama (2002)
Melanie Carmichael (Reese Witherspoon) is a self-professed Southern belle working as a buzzy fashion designer in New York. She is also engaged to the one of the city’s hottest bachelors, politician Andrew Hennings (Patrick Dempsey). The one problem is, Melanie is still married and in the process of divorcing her childhood sweetheart, Jake (Josh Lucas), a country bumpkin from Pigeon Creek, Alabama. Returning home, she confronts the truth about her past in this classic rom-com.
Sweet November (2001)
Nelson Moss (Keanu Reeves) is an advertising executive in San Francisco. At the DMV for a driving test, he runs into Sara Deever (Charlize Theron). She is the yin to his yang, an eccentric personality that contradicts his mild-mannered MO. Of course, they argue with each other, but in a surprise move, Sara asks Nelson to live with her for the month of November, promising to change his life for the better.
The Iron Giant (1999)
Hogarth Hughes is a young boy in Rockwell, Maine, who discovers a giant robot that has crash-landed on Earth. Befriending the colossus, Hogarth teaches it about humanity and kindness. But when government agents are alerted to the machine’s existence, it is up to Hogarth to save the misunderstood mechanical titan.
The Royal Tenenbaums (2001)
Royal Tenenbaum (Gene Hackman) is the ne’er-do-well father of three prodigies—celebrated playwright Margot (Gwyneth Paltrow), financial genius Chas (Ben Stiller), and tennis star Richie (Luke Wilson)—who maintains little contact with his family. When Royal discovers that his estranged wife, archaeologist Etheline (Anjelica Houston), is about to get engaged to a new man (Danny Glover), he feigns illness, so as to return home and reunite with his eccentric brood.
When Harry Met Sally (1989)
Sally Albright (Meg Ryan) and Harry Burns (Billy Crystal) are two recent college graduates forced to share a ride with each other. They are complete opposites, with differing views on myriad subjects. But they both agree that men and women are incapable of being platonic friends. After going their separate ways, they run into each other again, testing their shared perspective on relationships.
You’ve Got Mail (1998)
Kathleen Kelly (Meg Ryan) is the owner of a children’s bookstore on the Upper West Side of Manhattan. A fixture in the neighbourhood, she hangs with a ragtag crew when she isn’t perusing the “over 30s” chatroom on AIM or rereading Jane Austen. Facing stiff competition from a big chain store owned by Joe Fox (Tom Hanks), Kathleen also has to contend with a burgeoning online romance with an anonymous man. You can already guess who that turns out to be.
Lead image credit: Little Women / IMDb
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