Top 10 Rainy Day Movies

It may or may not actually be raining, but it’s a day where you want to see something a little sad—but not too sad. Whether it’s love or loss or just human connection, you want to stay inside and feel some emotions! These movies all fit the bill. Next time you’re feeling like this, give one of these movies a watch!

10. The Deer Hunter (1978)

The Deer Hunter

A war movie on a rainy day? There are few war movies—and, indeed, few movies—that have the emotional punch of this one. This one spends most of its time (about two-thirds of the movie) showing life before and after the war for the people who served, and that’s the real story here. If you want some serious action with your gloomy mood, this is the one for you.

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9. The Royal Tenenbaums (2001)

The Royal Tenenbaums

Probably Wes Anderson’s best film, this is a smart and quirky comedy/drama about a man who realizes he needs his family connections only after he’s razed them all to the ground. In an attempt to win them back, he fakes having a terminal illness, but the father, Royal, is so lacking in empathy that this proves much harder than he thought. The humor is great, but the drama is real, and there are some moments that will hit you right in the heart.

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8. Amelie (2001)

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In this French film, Amelie Poulain is a young woman so introverted she has trouble connecting with others, but so emotional that she has trouble abstaining. Her awkward attempts to reach out to others are fun to watch, but this is at its heart a deeply emotional film about human connection. The ending is uplifting, but you won’t be able to get through this movie without feeling some deep emotions.

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7. Good Will Hunting (1997)

Good Will Hunting

This film about a closeted genius with a troubled past focuses on Will Hunting transitioning from the carefree young adult life to the real world, where his hurts and hang-ups hold him back in all areas of his life. While funny at times and entertaining to watch, this is a film about healing from your pain and finding reasons to live. Anyone harboring pain of their own will find something to relate to here.

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6. The Apartment (1960)

The Apartment

For a 1960 comedy, this film captures depression more accurately than any movie for decades afterward. Equally hilarious and devastating, it captures that love and connection can be sweet, but also difficult and even damaging in a world full of broken people. When all you want is love, but everyone’s selling something else, life is hard. This is a personal favorite of mine and I’ll watch it whether it’s raining or not.

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5. Stand By Me (1986)

Stand By Me

We all remember the innocence of our youth, but it’s very hard to figure out exactly when we lost it. One day, we’re children, and somewhere years down the road, we realize we’re young adults and we’ve lost something and will never get it back. In this film, four young boys take a short trip to see a dead body, and it captures this loss of innocence and journey into young adulthood.

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4. Midnight Cowboy (1969)

Midnight Cowboy

A small-town cowboy journeys to the big city to realize his dreams and make it big. It’s a story we’ve seen before, but this one plays out differently. In this one, the cowboy is not at all prepared for the harsh realities of city life, and the city does not care at all about his dreams and ambitions. In fact, the city nearly destroys him. There’s also a very moving friendship between the two main characters that stands out as one of the best in film.

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3. Roman Holiday (1953)

Roman Holiday

A princess in the 1950s tires of the duties of her royal life and longs for a day free from the pressures and responsibilities that weigh on her daily. She makes her escape and meets a young newspaper photographer looking for the next big story. Over one amazing day, their connection grows deep and meaningful as they adventure through Rome. This is probably my favorite classic film, and it’s as deep and emotional as it is fun.

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2. Eternal Sunshine of the Spotless Mind (2004)

Eternal Sunshine of the Spotless Mind

Is it better to have loved and lost than to never have loved at all? This film gives characters the choice after the fact with a technology that erases memories. After a failed relationship, the main character has to choose if the memories of their good times together are worth the memories of their bad times together—and if future good times will be worth the future bad times. A great film about romantic connection between two flawed characters.

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1. Lost in Translation (2003)

Lost in Translation

Have you ever felt alone in a crowded room? This film shows us two lost souls who can’t find anyone who understands what that’s like—until they find each other while visiting Tokyo. Their connection isn’t romantic, but it’s so deep that neither of them quite knows what to do with it. Sometimes, being lost together can be just as sweet as being found.

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Runners Up

Lady Bird (2017), Little Miss Sunshine (2006), Sideways (2004)

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