Your Ultimate Fall Watchlist: 25 Cozy, Old School Movies You Forgot You Loved

Witchy chaos, old school romance, and all the nostalgic, cozy feels rolled into one binge-worthy list.

By Jenny Smith Mattfeldt | Published September 10, 2025

Some movies just feel like fall. The sweaters, the back-to-school energy, the magic, the nostalgia—it’s all there waiting for you like a warm blanket and a bowl of popcorn. Whether you’re craving a Molly Ringwald high school throwback, a witchy cult classic, or even an old western to shake up your autumn evenings, this list has all the cozy, old-school vibes to romanticize your fall.

Old-School High School Throwbacks. Because nothing says fall like back-to-school energy, varsity jackets, and a little teenage angst.

Sixteen Candles (1984)

Molly Ringwald navigating forgotten birthdays, crushes, and high school drama. It’s awkward, funny, and pure 80s nostalgia.

Drumline (2002)

Nick Cannon, Atlanta, and the high-stakes world of a college marching band. The ultimate back-to-school pump-up.

School of Rock (2003)

Jack Black sneaks his way into teaching and turns a class of kids into a rock band. Chaos + feel-good fun = perfect fall rewatch.

Matilda (1996)

A bookish girl with magical powers, a terrifying headmistress, and one of the most comforting childhood watches ever.

Love & Basketball (2000)

Childhood friends to lovers, basketball courts to adulthood—it’s romantic, cozy, and full of crisp fall sports energy.

Good Will Hunting (1997)

Boston in autumn, Matt Damon solving equations, Robin Williams breaking your heart in the best way. How do you like them apples?

Witchy, Spooky, and a Little Weird. Light a candle, grab a blanket, and lean into the magic. These picks are equal parts nostalgic, quirky, and just witchy enough to set the tone for spooky season.

Practical Magic (1998)

Sandra Bullock and Nicole Kidman as witchy sisters battling curses, heartbreak, and small-town gossip. Plus, that kitchen is fall cozy goals.

Hocus Pocus (1993)

The Sanderson sisters are chaotic, hilarious, and iconic. Halloween night in Salem doesn’t get more nostalgic than this.

Casper (1995)

A sweet ghost story with Christina Ricci, a haunted mansion, and plenty of 90s charm. Bonus points for fall’s favorite word: boo.

The Witches of Eastwick (1987)

Cher, Michelle Pfeiffer, and Susan Sarandon as small-town women with magical secrets and a devilish Jack Nicholson. Over-the-top perfection.

Beetlejuice (1988)

Tim Burton’s bizarre masterpiece with stripes, ghosts, and that unforgettable dinner party scene. Spooky, but make it fun.

Twitches (2005)

Tia and Tamera as long-lost twins who discover they’re witches? Peak Disney Channel fall nostalgia.

Death Becomes Her (1992)

If you were into Sabrina Carpenter's Taste video start here with the inspiration. Meryl Streep and Goldie Hawn feuding over love, immortality, and beauty in this dark, hilarious cult classic.

Ghostbusters (1984)

A crew of ghost-catchers in New York fighting slime and specters. It’s funny, quotable, and perfect for October.

Harry Potter and the Sorcerer’s Stone (2001)

There's something so deliciously nostalgic about the very first Harry Potter movie. From the first train to Hogwarts to the floating candles in the Great Hall, this is autumn magic bottled.

It’s the Great Pumpkin, Charlie Brown (1966)

Snoopy, Linus, and pumpkin patch wonder. Short, sweet, and essential.

Cozy Rom-Coms & Heart-Warmers. These are the movies that make you want to pull on a big sweater, sip something warm, and let your heart soften a little.

You’ve Got Mail (1998)

Meg Ryan in cozy knits, Tom Hanks in New York, and bookstores at their 90s peak. Fall in film form.

When Harry Met Sally (1989)

The crisp leaves, chunky sweaters, and sharp banter make this the ultimate autumn rom-com.

Planes, Trains and Automobiles (1987)

Thanksgiving travel has never been so funny or so heartwarming. Steve Martin and John Candy are perfection together.

Remember the Titans (2000)

A high school football team in Virginia comes together against all odds. Team spirit, heart, and fall Friday night lights energy.

Classic Old Westerns. Fall doesn’t just mean pumpkins and witches it’s also the perfect time to dive into old-school, John Wayne Americana. Dust, denim, wide open skies—these westerns are a cozy escape in their own way.

Rio Bravo (1959)

A sheriff, a saloon, and John Wayne holding down the fort. Gritty, old-school, but surprisingly warm at its core.

Red River (1948)

Sweeping cattle drives, tough decisions, and classic John Wayne grit. A western with all the big-sky drama.

The Sons of Katie Elder (1965)

Four brothers return home after their mother’s death. Family drama, shootouts, and that nostalgic western comfort.

So there you have it. 25 movies that practically smell like pumpkin candles and awkward teenage 80's love. Whether you’re in the mood for witchy chaos, back-to-school nostalgia, or a gritty old western, there’s something here to romanticize your fall nights. Now all that’s left is to grab a blanket, pour yourself something warm, and press play.

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