It’s September 22nd which means it’s finally autumn! It’s time for cosy films, warm blankets, and hot drinks as those vibrant green leaves turn to hues of orange, brown, and yellow! The films below are my favourite to watch this time of year. Most of them won’t come as a surprise, they’re always on these lists for a reason, but they’re always worth a watch (or rewatch)!
Practical Magic (1998)
Based on the book by Alice Hoffman, Practical Magic is about sisters Sally (Sandra Bullock) and Gillian (Nicole Kidman) who were born into a magical family. Having avoided magic for most of their lives, they now find themselves fighting against a family curse when Sally’s husband (Mark Feuerstein) dies in an accident, and Gillian accidentally kills her abusive boyfriend (Goran Visnjic), all while policeman Gary Hallet (Aidan Quinn) keeps a close eye. Directed by Griffin Dunne, Practical Magic is a cosy film about love, fate, and sisterhood that exudes cosy and witchy imagery, as well as entertaining performances from Bullock and Kidman.
Stepmom (1998)
Divorced couple Jackie (Susan Sarandon) and Luke (Ed Harris) are struggling to co-parent their two children, Anna and Ben, when Luke adds his younger girlfriend Isabel (Julia Roberts), a successful fashion photographer, into the mix. Jackie and Isabel dislike one another but when Jackie discovers she is terminally ill, the two women realise they must put aside their differences to celebrate life to the fullest and help Anna and Ben deal with the upcoming loss. Stepmom is packed with gorgeous autumnal scenes and fall fashion, all while exploring deep themes with raw emotion. It’s a real tear-jerker and an all-around great movie thanks to its exceptional writing and talented cast!
Mona Lisa Smile (2003)
In the early 50s, Katherine Ann Watson (Julia Roberts) accepts an Art History teaching position at Wellesley College. Upon discovering that her students have memorised their textbooks and syllabus, she sets out to introduce the young women to modern art, teaches them to think critically about what good art is, and challenges their traditional and conversative beliefs, inspiring them to achieve more than marriage. In addition to Roberts, Mona Lisa Smile‘s star-studded cast also features Kirsten Dunst, Julia Stiles, Maggie Gyllenhaal, and Ginnifer Goodwin. Lily Rabe and Krysten Ritter even appear in minor roles, if you can spot them, alongside Tori Amos as a wedding singer. Set in autumn, Mona Lisa Smile explores feminist themes, including women’s roles and worth in society.
Cruel Intentions (1999)
Set in New York City, wealthy and manipulative teenagers Kathryn (Sarah Michelle Gellar) and Sebastian (Ryan Phillippe), who are also step-siblings, decide to wager a bet: if Sebastian can bed Annette Hargrove (Reese Witherspoon), the headmaster’s daughter, before the end of the summer, Kathryn gets his vintage Jaguar XK140. But if he wins, Kathryn will finally have sex with him. Cruel Intentions is a hell of a 90s film featuring many dark and taboo themes, such as an incestual relationship, many of which are played for laughs. It’s a film that would never be made today, being too politically incorrect, but the memorable saliva-dripping kiss between Gellar and Selma Blair is still considered iconic today. What could be better than exploring the antics of rich Upper East Side teenagers almost a decade before Gossip Girl?
Donnie Darko (2001)
Donnie Darko stars a young Jake Gyllenhaal as the titular Donnie Darko, a troubled teenager who starts being plagued by visions of a large bunny rabbit named Frank after narrowly escaping a bizarre accident. Frank informs him the world will end in 28 days, 6 hours, 42 minutes, and 12 seconds. Written and directed by Richard Kelly, Donnie Darko explores heavy themes, including mental illness, teenage angst and isolation, finding purpose, determinism, and even showing the conflict between progressive and conservative views—but it does treat many of these with levity, allowing for humour throughout. The themes, visuals, and soundtrack are perfectly dark and autumnal, making it a perfect watch around this time of year. Donnie Darko also stars Maggie Gyllenhaal, Jena Malone, Mary McDonnell, James Duval, Davleigh Chase, Drew Barrymore, and Patrick Swayze, with Seth Rogen and Ashley Tisdale in minor roles.
It Follows (2014)
When teenager Jay (Maika Monroe) has sex with a guy she is seeing, she falls victim to a fatal curse that is passed via sexual intercourse. Death, taking the form of a friend or stranger, will slowly follow her until it either catches her or she passes it to another person. Many have taken It Follows to be a metaphor for STDs, but writer-director David Robert Michell said the film is based on anxiety dreams. When asked where “it” comes from, he said it’s like “when you’re in a nightmare and there’s no solving the nightmare,” but “love and sex” are ways to temporarily push death away. Shot with wide-angle lenses, the film’s gorgeous autumnal scenery and cinematography, in addition to its eerie and unescapable monster, were influenced by George A. Romero, John Carpenter, and photographer Gregory Crewdson. A sequel titled They Follow will begin filming next year!
Dead Poets Society (1989)
Dead Poets Society is the sibling of Mona Lisa Smile. Set in 1959 during autumn/winter, Todd Anderson (Ethan Hawke) starts his junior year of high school at Welton Academy, an all-male boarding school in Vermont. He and his friends are surprised by the unorthodox teaching methods of the new English teacher, John Keating (Robin Williams), who uses poetry to inspire the students to rebel against convention and make the most of every day. Williams gives a memorable and heartfelt performance, one that earned him an Academy Award nomination for Best Actor. Dead Poets Society also features many complex themes and characters, providing something for everyone to relate to.
School of Rock (2003)
Nothing says autumn like being back at school after the summer holidays. Fired from his band and feeling pressure from his roommate Ned (Mike White) to pay his share of the rent, Dewey (Jack Black) gets a job as a substitute teacher at a private school by posing as Ned. After seeing how talented his students are in music class, Dewey trains them together as a large band, getting them ready to audition for Battle of the Bands. School of Rock is a fun and uplifting watch. Black excels in this role as his entertaining and eccentric self, and the cast of children (including Miranda Cosgrove) are diverse and convincing. It’s truly heartwarming to watch what Dewey does for these kids, and what they, in turn, do for him.
Clue (1985)
Based on the board game Cluedo, Clue finds six diverse dinner guests (Eileen Brennan, Madeline Kahn, Christopher Lloyd, Michael McKean, Martin Mull, and Lesley Ann Warren) gathered at the mansion of their host, Mr. Boddy (Lee Ving), who turns up dead after it’s revealed that he was blackmailing all of them. The guests and Boddy’s chatty butler (Tim Curry) must figure out which one of them is the killer before the body count increases. Nothing beats a mystery—or a board game—when it’s chilly outside, but Jonathan Lynn and John Landis had the good sense to make Clue a black comedy, which makes it even better. The film also has multiple different endings, inspired by the nature of the board game. It’s simply just good fun!
Knives Out (2019)
Daniel Craig leads an ensemble cast as famed private detective Benoit Blanc. He is hired anonymously to investigate the death of wealthy mystery novelst, Harlan Thrombey (Christopher Plummer), who appeared to commit suicide on the eve of his 85th birthday. Blanc interviews Harlan’s dysfunctional family (Chris Evans, Jamie Lee Curtis, Michael Shannon, Toni Collette, Don Johnson, Katherine Landford, so forth) and his devoted staff, including his nurse, Marta (Ana de Armas), while sifting through clues and red herrings. It quickly becomes clear that his greedy family members have motive, but Marta is curiously caught in the crossfire. Rian Johnson successfully rejuvenated the mystery genre with Knives Out, a clever whodunnit that nails its cast, set design, tone, and story, in addition to exploring class warfare and wealth inequality, as well as race and immigration. It remains entertaining upon a rewatch!
October Kiss (2015)
Set around Halloween, Poppy Summerall (Ashley Williams) is hired as a nanny to two young children by widowed workaholic Ryan Lawson (Sean Jaeger). Poppy’s creativity and optimism is a gift to the family as she teaches them about the importance of family, unconditional love, and the joy found in everyday life. Williams’ natural effervescence is infectious, and she and Jaeger have excellent chemistry. The kids are adorable and most scenes are filled with warming Halloween decorations. Despite it being a Hallmark TV movie, October Kiss is a charming, heartwarming, and delightful family film.
Halloweentown (1998)
On her 13th birthday, Marnie (Kimberly J. Brown) discovers she’s a witch when she, alongside her brother Dylan (Joey Zimmerman) and sister Sophie (Emily Roeske), follow their grandmother Aggie (Debbie Reynolds) through a secret portal that transports them to Halloweentown—a magical place separated from the human world where ghosts and ghouls, witches, warlocks, and werewolves live together in relative harmony. Marnie is excited but soon finds herself battling the town’s evil warlock who threatens to take over the mortal world. Halloweentown, the fourth ever Disney Channel Original Movie, is effective in navigating the typical themes of adolescence, all while creating an original world that truly feels magic. The charming family film became a Halloween staple for kids like me who watched this every year during the 2000s.
Halloween (1978)
Considered the first slasher to popularise the genre, John Carpenter’s Halloween is another Halloween staple. 15 years after murdering his sister on Halloween Night, Michael Myers (Nick Castle) escapes from a mental hospital and returns to his smalltown in Illinois to kill again. He begins stalking teenager Laurie Strode (Jamie Lee Curtis), whose father is trying to sell Michael’s long-abandoned childhood home. Halloween is celebrated for its slow and focused stalking camerawork, as well as Carpenter’s iconic score, which set the standard for slashers throughout the 80s. The film has been written about extensively in film academia, but it doesn’t take a scholar to appreciate the inventive filmmaking on display here.
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