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'When Harry Met Sally' Is Turning 35! Here's Where To Stream The Best Meg Ryan Movies.

meg ryan movies fall movies when harry met sally
Castle Rock Entertainment/Nelson Entertainment/Columbia Pictures

There's nothing like fall movies to get us in the mood for cozy season. The aesthetics of orange, red, and yellow leaves (as well as plots about friends and family) give us an instant mood boost. Meg Ryan is one of our favorite leading ladies, and while she just returned to the screen in 2023 for What Happens Later, we're getting ready to celebrate the anniversary of MY favorite Meg Ryan movie: When Harry Met Sally.

The iconic rom-com turns 35 on July 21, and in honor of the milestone, we rounded up our go-to Meg Ryan movies that will give you ALL the fall feels (as well as some of her other best hits). We also spoke with Kristin Marguerite Doidge, the author of Nora Ephron: A Biography, for a look into the director's vision when it came to bringing these stories to life. Grab your favorite fuzzy socks, an Apple Crisp Macchiato, and bookmark these titles for your next movie marathon.


When Harry Met Sally — Rent on Amazon Prime

When Harry Met Sally

Castle Rock Entertainment/MGM

This iconic Meg Ryan movie features Ryan and Billy Crystal as the namesake duo. Wrestling with the idea of whether men and women can just be friends, the 12-year story took seven drafts for Ephron to feel like Harry and Sally's relationship was developed enough for audiences.

We love common tropes like slow burns and friends-to-lovers, but we also love the fact that Ephron switched up the common rom-com expectations by using Harry's cynicism (instead of an outside obstacle) as the driving force behind keeping the couple apart.

According to Doidge, while the aesthetic of the film can be credited to director Rob Reiner, Ephron's screenplay is such a big part of the movie's DNA that it's connected to every aspect of the film: "From the stunning fall leaves in Central Park to Meg’s iconic chocolate brown bowler hat, [it’s] become known as a 'Nora' movie."

There's something special about watching these friends-turned-lovers help each other through the ups and downs of life, and with details like Ryan's iconic white sweater and walking through the foliage in Central Park, we get excited for fall as soon as the opener starts playing.

Sleepless In Seattle — Stream on Max

sleepless in seattle meg ryan movies

TriStar Pictures

Sleepless In Seattle takes us on a journey around the country when widower Sam's (Tom Hanks) son Jonah reveals Sam's quest for love to the world via talk radio. Annie (Ryan) hears the show and decides to write Sam and ask him to meet her at the top of the Empire State Building on Valentine's Day. Even though the movie takes place after the new year, the romantic and family themes of the plot give us those same cozy feelings.
Sleepless feels very intimate because of Ephron's down-to-earth approach to telling the story. Ephron was incredibly detailed with character interactions, like when Sam realizes that Annie peels an apple just like his late wife. It's those small points in the film that make the characters feel relatable, even if we've never been in their specific scenario before.
"What’s the detail you remember about someone who leaves?” executive producer Lynda Obst says in the biography. “It’s the touching detail that you’ll never see again — it is touching, but it has no sentiment. It has uniqueness, texture, smell.”
The layered clothing and rainy setting add an aesthetic touch that's perfect for fall, but it's really the will-they-won't-they back-and-forth that makes us root for the couple. From Sam's reluctance to meet Annie to when their eyes meet from afar, we as the audience see how easy it is to almost miss your chance with someone — and how important that chance is in the first place.

You've Got Mail — Rent on Prime Video

you've got mail

Warner Bros. Pictures

If you ask us, You've Got Mail might have the best fall vibes of all of Meg Ryan's movies. A cozy bookstore on the Upper West Side and plenty of sweaters, coffee, and pastries? Count us in. Ryan's Kathleen is pen pals with Tom Hanks' Joe, even though neither of them realizes they're real-world competitors.

"When you see You’ve Got Mail, you’re seeing Nora,” cinematographer John Lindley says in the biography. “What you’re seeing is her outlook on life, which is to be happy and embrace change.”

In an age of texting and swiping, being pen pals with someone feels like a classic take on romance that's extra swoon-worthy. The dreams and stubbornness of the leads make us root for them, and knowing their unknown feelings for one another makes this romance all the sweeter. Not to mention that it takes place in a bookstore, which is one location that will always make us feel at ease.

What Happens Later — Stream on Hulu with SHOWTIME

What Happens Later

Bleecker Street

Willa and Bill aren't expecting to see each other at the airport — or to realize they're still attracted to each other. (They also still annoy each other, but that's less important). When a snowstorm rolls in and their flights are cancelled, Willa and Bill are left alone at the airport with nothing but their pasts, a witty airport announcer, and fate to keep them company.

kate and leopold

MIRAMAX

"What [Ephron] may not have anticipated is just how [fragmented] and divisive sections of America would become," Doidge writes. "Is that part of what makes her particular brand of optimism so appealing in this current moment? Possibly." When we're anxious or feeling sad, films like these offer us some light. We know that even though the characters go through realistic and difficult times in their lives, things turn out all right in the end.

These Meg Ryan movies are a great way to get you in the mood for fall. While we're still months away from carving pumpkins or gathering around the table for Friendsgiving, it's never too early for a cup of tea and a candle to set the scene.

Other Meg Ryan Movies We Love

  • Top Gun on Amazon
  • Promised Landon Apple TV
  • Joe Versus the Volcano on Amazon
  • When a Man Loves a Woman on Amazon
  • Addicted to Love on Apple TV
  • Anastasia on Disney+
  • City of Angels on Amazon
  • Hanging Up on Pluto TV
  • Kate & Leopold on Max
  • Tag us with your favorite Meg Ryan movies on Instagram and subscribe to our email newsletter for more TV and movie recommendations.

    Featured image via Castle Rock Entertainment/Nelson Entertainment/Columbia Pictures

    This post has been updated.

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