The Best Fall Movies of All Time

Nothing says fall quite like lighting a candle that smells like honey crisp apples and cinnamon, curling up on the couch with warm apple cider, and scrolling endlessly on Netflix only to end up watching your favorite movie again.

It's a seasonal ritual of sorts, and now Erin is sharing her top six favorite fall movies to help you narrow down your search. Enjoy!

When Harry Met Sally

When Harry Met Sally is a 1989 romantic comedy starring Billy Crystal and Meg Ryan, this hysterical story starts when they meet in Chicago just before sharing a cross-country drive through twelve years of chance encounters in New York City. The film tries to answer the question "Can men and women ever just be friends?" You'll quickly fall in love with the charming NYC scenery and the genuine chemistry these two share on-screen.

Meg Ryan and Billy Crystal in "When Harry Met Sally." Moviestore/Shutterstock

Sweet November

According to Erin, Sweet November is a 2001 romantic drama "so 90s that it qualifies as a 90s film." This movie stars Keanu Reeves and Charlize Theron and follows two strangers that fall in love and spend a month together. Can you guess which month? 

"Charlize Theron's character was a major style and home inspiration to me as a teenager, and I think it's safe to say it had a lasting effect on me. I'm still into that look. All of it. Her apartment is like the bohemian counterpart to Meg Ryan's You've Got Mail apartment, so I'm all in." — Erin

You've Got Mail

Three little words: Watch. It. Now. 

You've Got Mail stars Meg Ryan, an independent bookstore owner with a charming and fiery spirit, and Tom Hanks, a corporate, mega bookstore developer. In real life, they hate each other with a burning passion, but unbeknownst to them, they have been falling in love with one another online. What happens when they find out the truth?

(Spoiler: Do not watch the video below if you haven't watched the movie yet.)

Good Will Hunting

This 1997 psychological drama stars the ever-lovable Robin Williams, a young Ben Affleck, and Matt Damon. Wikipedia says it best, "The film follows 20-year-old South Boston janitor Will Hunting (Damon), an unrecognized genius who, as part of a deferred prosecution agreement after assaulting a police officer, becomes a patient of a therapist and studies advanced mathematics with a renowned professor. Through his therapy sessions, Will re-evaluates his relationships with his best friend (Affleck), his girlfriend, and himself, facing the significant task of confronting his past and thinking about his future."

It's a comeback story, an honest dialogue about life, and an all-around feel-good story that makes you want to drive into the sunset or "go see about a girl."


Play this song while you read it. You'll be ready to finally do that laundry you've you've been neglecting for three weeks or go bear hunting with a switch when it's all said and done.

This is a 1993 American biographical sports film. Different than any of the other romantic comedies listed here, this story is an account of the life of Daniel "Rudy" Ruettiger, son of a working-class family. He has dreams of playing football at the University of Notre Dame. It's a classic, and it'll make the least exciting football fan stand to their feet and chant "Rudy, Rudy, Rudy" at the end.

Cinderella Man

An Irish-American boxer gives up boxing after breaking his hand in the ring. It's a relief and a burden to his wife, but they have to make ends meet somehow. He begins working as a longshoreman and becomes skilled at using his left hand. Through a string of events, he quite literally fights his way back to the top. It's a classic underdog movie. You'll be rooting for this story, and it'll be a left jab to the heart by the end.  


If you're more of a television show fan, we know of a little show called Home Town. You can watch now on Discovery+ or shop Erin and Ben's favorite things here.