Fall is my favorite time of the year. It’s the cooldown after these increasingly hot summers. Cool mornings, even cooler nights. And those chilly evenings make for perfect cozy stay-at-home nights with a blanket, a nice warm drink (I personally go for any variance of tea) and a good movie. Here are my favorites that I think encapsulate the season, plus an honorable mention. 

‘It’s the Great Pumpkin, Charlie Brown’ (Available on Apple TV+)

Arguably the most classic movie here, “It’s the Great Pumpkin Charlie Brown” is short and sweet, clocking in at only 25 minutes, making it the perfect appetizer or dessert for your night. 

“It’s the Great Pumpkin, Charlie Brown ” followed the immense success of “A Charlie Brown Christmas,” and focuses on Linus as he awaits the arrival of the mythical Great Pumpkin, much to the humor of his friends. Despite releasing nearly 60 years ago in 1966, the animation still holds up and the movie itself is still deeply charming. Nothing beats Snoopy. Nothing beats Charlie Brown. Nothing beats the Peanuts. 

‘When Harry Met Sally’

My personal favorite of everything here, “When Harry Met Sally” is the creator of the modern romcom, and a pioneer in dialogue, set design, costume design and character dynamics.

The film completely encapsulates fall and winter in New York, whether it’s through a walk in Central Park decorated by orange-leaved trees and dressed with Billy Crystal’s iconic leather jacket and Meg Ryan’s fashionable handbag and hat, or Harry Connick Jr.’s legendary Grammy-winning jazz soundtrack that perfectly accompanies the film and sets the mellow fall tone throughout. “When Harry Met Sally” is an absolute must, whether it’s your first time watching or your (my) twentieth. 

‘Planes, Trains and Automobiles’ (Available on Paramount+)

There are dozens upon dozens of Halloween movies, and even more Christmas movies. But there are a slim amount of Thanksgiving movies, and even fewer that have really cracked through to the mainstream. “Planes, Trains and Automobiles” is arguably not only one of the most iconic Thanksgiving movies of all time, but the only iconic Thanksgiving movie (“A Charlie Brown Thanksgiving” withstanding). 

John Candy and Steve Martin are hilarious as two men consistently caught in the most unfathomable and inconvenient scenarios imaginable, as they try to simply get home from Thanksgiving dinner. “Planes” is one of the most underrated holiday movies of all time in my opinion, and I’ve watched it every year since I first saw it. 

‘The Silence of the Lambs’ (Available on MAX)

In the mood for something a little more scary? I just rewatched “The Silence of the Lambs” and was absolutely enthralled. One of the most well-paced thrillers of all-time, Jonathan Demme’s 1991 film, adapted from Thomas Harris’s novel of the same name, won five Oscars: Best Picture, Best Actress (Jodie Foster), Best Actor (Anthony Hopkins), Best Director (Demme) and Best Adapted Screenplay (Ted Dally). 

The film opens with Foster running through the orange-stricken woods, immediately setting the mood of not just the season, but the movie itself. She’s all alone in this, and can’t stop running. 

‘Gone Girl’ (Available on MAX)

Good for her! Adapted from Gillian Flynn’s book of the same name, “Gone Girl” tells the cold story of the troubled romance between Nick and Amy Dunne, played by Ben Affleck and Rosamund Pike respectively. Pike received a nomination in Best Actress for her work, the film’s lone Oscar nomination. 

The who-dunne-it (Not my best work) is a fall mainstay in my watchlist, and serves as the perfect entree for not only the season, but director David Fincher’s new film “The Killer,” which releases on Netflix on November 10, and that I will be seeing this Saturday. 

HM – ‘All Too Well: The Short Film’ (Available on YouTube)

This is sort of cheating, but I had to mention it. My favorite music video of all time, “All Too Well: The Short Film” is in my opinion, the pinnacle of Taylor Swift’s career. The song is absolutely phenomenal and gut-wrenching, and the video conveys that tenfold. 

Sadie Sink and Dylan O’Brien portray the ill-fated relationship between Swift and actor Jake Gyllenhaal, as they make their way through the season of fall, and the fall of their relationship. Swift captures the season stunningly with her warm set designs and cozy costumes. 

If you really want a treat, watch Swift’s “Saturday Night Live!” performance of the song, which is accompanied by the music video playing in the background.