The Best Fall Movies And How To Watch Them

Meg Ryan and Billy Crystal in When Harry Met Sally

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It’s that time of year again — the days are shorter, there’s a crispness in the air, and the leaves are changing. What better way to bring in the autumn months than with a marathon of the best fall movies. With classic romantic comedies like When Harry Met Sally, instant classics like Knives Out, and oh so many sports movies, there are countless great films to fill up the hours of those cool September weekends, long October nights, and lazy November Sundays. To help you get the most out of your time, we’ve put together a list of the best fall movies and how to watch them.

Meg Ryan and Billy Crystal in When Harry Met Sally

When Harry Met Sally (1989)

When Harry Met Sally, directed by Rob Reiner, tells the story of Harry Burns (Billy Crystal) and Sally Albright (Meg Ryan), and the different stages of their relationship as they go from two college graduates arguing about the viability of male-female friendships to soulmates.

Why it’s a great fall movie: Some of the movie’s best scenes take place during the fall, particularly Harry and Sally talking about recurring sex dreams while walking through New York and the hilarious football game where Harry tries to talk about his divorce with Jess (Bruno Kirby) in the middle of the wave.

Stream When Harry Met Sally on HBO Max.

Rent/Buy When Harry Met Sally on Amazon.

Buy When Harry Met Sally on DVD/Blu-ray on Amazon.

Ana de Armas in Knives Out

Knives Out (2019)

When novelist Harlan Thrombey (Christopher Plummer) dies under suspicious circumstances, detective Benoit Blanc (Daniel Craig) is brought in to investigate. With every family member a suspect, it’s up to Blanc to get to the bottom of this murder mystery.

Why it’s a great fall movie: Maybe it’s the sweaters, leaves on the ground, or a general sense of chilliness that makes Rian Johnson’s 2019 whodunit, Knives Out, such a fun treat to revisit each fall. No matter what draws you back to the unique story, this is a must for anyone looking for one of the best movies on Amazon.

Stream Knives Out on Amazon.

Rent/Buy Knives Out on Amazon.

Buy Knives Out on DVD/Blu-ray on Amazon.

The October Sky cast

October Sky (1999)

Homer Hickam (Jake Gyllenhaal) and a group of friends make a rocket of their own, even if everyone else but their teacher, Miss Riley (Laura Dern), thinks they're crazy. Miss Riley soon becomes all the support they need.

Why it’s a great fall movie: Joe Johnston’s October Sky has fall written all over it. Cold air, fallen leaves in West Virginia, and the October 1957 launch of Sputnik 1, are three examples in this great biographical drama.

Stream October Sky on Peacock.

Rent/Buy October Sky on Amazon.

Buy October Sky on DVD/Blu-ray on Amazon.

The Dead Poets Society cast

Dead Poets Society (1989)

At the start of the fall 1959 semester at the prestigious Welton Academy preparatory school, unconventional yet influential English teacher John Keating (Robin Williams) comes into the lives of his students, forever changing the way they look at themselves and the world around them.

Why it’s a great fall movie: Just like wind shaking leaves from a tree, John Keating gives his students the knowledge and confidence to fall from their branches in Peter Weir’s Academy Award-winning coming-of-age drama, Dead Poets Society. The teenage boys undergo a tremendous shift in their lives just as the seasons change in the early days of autumn, a change that will forever stick with them.

Rent/Buy Dead Poets Society on Amazon.

Buy Dead Poets Society on DVD/Blu-ray on Amazon.

Sean Astin in Rudy

Rudy (1993)

What Rudy Ruettiger (Sean Astin) lacks in size, he makes up for tenfold with his drive and positive outlook as he tries to pull off the impossible by joining the famed Notre Dame Fighting Irish football team as a walk-on.

Why it’s a great fall movie: David Anspaugh’s 1993 classic Rudy will forever be one of the best sports movies of all time thanks to its unforgettable story of an underdog going against the grain to make his dream a reality, no matter what it takes or costs. As the fall football season gets into full swing, there’s no better time than now to watch this timeless classic.

Stream Rudy on Amazon.

Rent/Buy Rudy on Amazon.

Buy Rudy on DVD/Blu-ray on Amazon.

The Fantastic Mr. Fox cast

Fantastic Mr. Fox (2009)

After being a mild-mannered fox with a wife, son, and weekly newspaper column, Foxy Fox (George Clooney) grows tired of his predictable life and decides to go back to his old ways. When the wise-cracking fox, his family (voiced by Meryl Streep and Jason Schwartzman), and friends become the targets of three local farmers, they finds themselves in a race for survival.

Why it’s a great fall movie: One of the best Wes Anderson movies, this 2009 adaptation of Roald Dahl’s Fantastic Mr. Fox just looks like a fall movie with its warm color palette and visuals of fruit and grain harvests.

Stream Fantastic Mr. Fox on Disney+.

Rent/Buy Fantastic Mr. Fox on Amazon.

Buy Fantastic Mr. Fox on DVD/Blu-ray on Amazon.

Jennifer Lawrence and Bradley Cooper in Silver Linings Playbook

Silver Linings Playbook (2012)

Just when it seems like things can’t get much crazier for Pat Solitano (Bradley Cooper), he meets recently widowed Tiffany Maxwell (Jennifer Lawrence). As a way for both to move on with their lives following episodes of severe trauma, the pair enter a dancing competition.

Why it’s a great fall movie: Set in Philadelphia in the middle of the NFL season, David O. Russell’s Silver Linings Playbook is a damn near perfect fall film. With an inspirational story about living with a mental illness, rebuilding bridges, and finding new meaning in life, it’s also one of the best movies on Netflix.

Stream Silver Linings Playbook on Netflix.

Rent/Buy Silver Linings Playbook on Amazon.

Buy Silver Linings Playbook on DVD/Blu-ray on Amazon.

John C. Reilly and Kevin Costner in For Love of the Game

For Love Of The Game (1999)

Billy Chapel (Kevin Costner) is in the middle of throwing a perfect game, but he can't stop thinking about his on again, off again relationship with Jane Aubrey (Kelly Preston) between each New York Yankee batter.

Why it’s a great fall movie: Sam Raimi's For Love of the Game is part baseball movie and part love story about a couple destined to be a part of each other’s lives despite the odds. A lot of the movie takes place in various seasons, but it always comes back to that fateful fall day in New York.

Stream For Love of the Game on Showtime.

Rent/Buy For Love of the Game on Amazon.

Buy For Love of the Game on DVD/Blu-ray on Amazon.

The Good Will Hunting cast

Good Will Hunting (1997)

Will Hunting (Matt Damon) isn't your typical genius, but behind that hardened exterior is a level of intellect few have seen before. When Will has a run-in with the law, professor Gerald Lambeau (Stellan Skarsgard) takes him under his wing and introduces him to therapist Sean Maguire (Robin Williams).

Why it’s a great fall movie: There is something about Gus Van Zant’s Good Will Hunting, which was written by stars Matt Damon and Ben Affleck, that shouts autumn. Conversations in Boston Common, stories set in Red Sox World Series lore, and talk of Sunday afternoons watching the Patriots play all come to mind.

Stream Good Will Hunting on Starz

Rent/Buy Good Will Hunting on Amazon.

Buy Good Will Hunting on DVD/Blu-ray on Amazon.

Denzel Washington in Remember the Titans

Remember The Titans (2000)

T.C. Williams High School becomes integrated for the 1971 school year, forcing football players of different walks of life to be teammates. Under the leadership of new head coach Herman Boone (Denzel Washington), the players’ triumphs on the field pale in comparison to the ground they break off the gridiron.

Why it’s a great fall movie: Remember the Titans remains not only one of the best high school football movies but also one of the best sports movies in general. And, with the movie primarily taking place during the Titans’ 1971 football season, there’s no reason not to consider this one of the best fall movie options.

Stream Remember the Titans on Disney+.

Rent/Buy Remember the Titans on Amazon.

Buy Remember the Titans on DVD/Blu-ray on Amazon.

Tobey Maguire and Michael Caine in The Cider House Rules

The Cider House Rules (1999)

Homer Wells (Tobey Maguire) lives at a Maine orphanage under the care of Dr. Wilbur Larch. But, when Wilbur tells Homer he wants him to take over the orphanage and the care of those in need of his services, Homer flees to find a life of his own, connecting with Candy Kendall (Charlize Theron), the girlfriend of World War II pilot Wally Worthington (Paul Rudd).

Why it’s a great fall movie: There are few places as beautiful as New England on a crisp fall day, and Lasse Hallström’s 1999 coming-of-age drama The Cider House Rules proves that.

Stream The Cider House Rules on Cinemax.

Rent/Buy The Cider House Rules on Amazon.

Buy The Cider House Rules on DVD/Blu-ray on Amazon.

Saoirse Ronan and Timothée Chalamet in Little Women

Little Women (2019)

Jo March (Saoirse Ronan) sets out to write about the bond she shares with her three sisters and their life in Massachusetts. Inspired by their extraordinary lives and everything that has happened to them over the years, Jo hopes to capture the magic of sisterhood.

Why it’s a great fall movie: Greta Gerwig’s 2019 adaptation of Little Women makes some slight deviations from Louisa May Alcott’s novel of the same name, but the core of this timeless story remains the same. And it’s true that Little Women features all the seasons throughout its sprawling narrative, but one can’t help but think of fall whenever watching it.

Stream Little Women on Starz.

Rent/Buy Little Women on Amazon.

Buy Little Women on DVD/Blu-ray on Amazon.

Steve Martin and John Candy in Planes, Trains and Automobiles

Planes, Trains And Automobiles (1987)

Neal Page (Steve Martin) wants to be home for Thanksgiving, but fate has other plans. When his travel plans are thrown out the window, Neal is trapped with Del Griffith (John Candy), who becomes his companion in this heartfelt buddy road trip movie.

Why it’s a great fall movie: There are few Thanksgiving movies that compare to John Hughes’ Planes, Trains and Automobiles. With one side-splitting moment after another and a lot of weight in the final act of the movie, this beloved classic features a great story about the meaning of family and friendship.

Stream Planes, Trains and Automobiles on Hulu.

Rent/Buy Planes, Trains and Automobiles on Amazon.

Buy Planes, Trains and Automobiles on DVD/Blu-ray on Amazon.

As the temperature continues to drop and the leaves start to change, hopefully these movies remind you of the beauty of fall and its warm memories. However, if you’re looking for something new, take a look at our list of all the remaining 2021 new movie releases.

Philip Sledge
Content Writer

Philip grew up in Louisiana (not New Orleans) before moving to St. Louis after graduating from Louisiana State University-Shreveport. When he's not writing about movies or television, Philip can be found being chased by his three kids, telling his dogs to stop barking at the mailman, or chatting about professional wrestling to his wife. Writing gigs with school newspapers, multiple daily newspapers, and other varied job experiences led him to this point where he actually gets to write about movies, shows, wrestling, and documentaries (which is a huge win in his eyes). If the stars properly align, he will talk about For Love Of The Game being the best baseball movie of all time.