Movies to watch when you want a good cry

A collage of photos from all the movies on the list. From the bottom left: The Lake House, Dead Poets Society, A Walk to Remember, How to Make a Million Before Grandma Dies, 20th Century Girl, La La Land. Illustration by Khue Tran.

By Khue Tran

If you don’t want to cry, seriously, don’t watch these.

Really? Are you still here? Well, you asked for it. 

It’s a Saturday night and you feel like watching a movie — a sad one — so you scroll through Netflix or TikTok to find recommendations, but by the time you find a few, you’d be too lazy to start the movie. I figured I’d pile up a list of films that I have had a good bawl over so that you won’t have to look for it when that mood hits you. In chronological order, here are my top six favorite sad movies of all time!

1. Dead Poets Society (1989)

This movie needs no introduction. Whether you have or haven’t watched it (or maybe you haven’t watched it in a really long time), Dead Poet Society is one of those films that everyone knows and no one hates. 

Director Peter Weir welcomes us into the life of the first-year students at Welton Academy, an all-boys boarding school that has just hired a new English teacher with the name of John Keating (Robin Williams). Despite the institute’s reputation for strict academic disciplines, Keating had different lessons in mind. 

Dead Poets Society opens a door of perspective for those who had always followed the old-fashioned methods of discipline, proving to the audience that a person’s possibilities are endless, even if some roads seem more difficult than others.

2. A Walk to Remember (2002)

After being a reckless and troubled teenager all his high school years, Landon Carter (Shane West) found a change of scenery in his life when he became friends with his polar opposite classmate Jamie Sullivan (Mandy Moore), the reverend’s daughter. Together, Landon helps Jamie check all the boxes on her bucket list.

This is a classic example of an early 2000s romance movie that you wish they still made. Everything from the plot to the cast’s chemistry retells about love and growth. 

3. The Lake House (2006)

After failing to save a patient in a car accident, doctor Kate Forster (Sandra Bullocks) decides to visit her old lake house as an escape from the city. She began exchanging letters to the new tenant of the home through their mailbox, which she soon discovers connects her to an Alex Wyler (Keanu Reeves) two years prior to her time.

Out of all the movies I have watched, none of them have made me cry as much as this movie has. Sandra Bullocks and Keanu Reeves’ performances leave you eager to see how their journey unfolds, even if it’s a trope you’ve seen a hundred times before.

4. La la Land (2016)

Through a series of musical numbers and colorful cinematography, this movie talks about the hustle that aspiring performers go through in hopes that they will land a spot in Hollywood. Although different in personality and interest, Mia Dolan (Emma Stone), a barista who dreams about an acting career, and Sebastian Wilder (Ryan Gosling), a jazz enthusiast and keyboard player, sparked an unexpected connection for their passion for their careers.

Those who have watched and loved this picture know that nothing beats the first watch — even if you’ve watched it 100 times. So if you’re one of the people who haven’t, enjoy your first watch. 

5. 20th Century Girl (2022)

We all wish we had a friend like 20th Century Girl’s main character, Bo Ra Na (Yoo Jung Kim). The story follows 40-year-old Na as she reminisces the adventures that began when her bedridden friend, Yeon Du Kim (Yoon Seo Roh) had to miss months of school for medical treatment, Na became determined to do whatever it takes to bring school life to her, even if it meant searching for a hallway crush she once passed by. 

Like many coming-of-age movies, this film is centered around the enthusiastic youth and the relationships they build as they live in the moment and let their emotions take the lead. By the 15-minute mark, you would have formed a love for the characters that director Woo Ri Bang brought to life; you would laugh when they laugh and cry when they cry. 

6. How to Make a Million Before Grandma Dies (2024)

Down on his luck, M (Billkin) suddenly found an opportunity to make a fortune when his grandmother got diagnosed with cancer. He quits his job to take care of her with the hopes of getting something out of her fortune. With its charming characters and familial love, director Pat Boonnitipat invites you into the family of M and his grandmother Amah (Usha Seamkhum). 

From stunning shots to intricate use of color, this movie’s cinematography will leave you awestruck as it takes you on a trip to the local version of Talat Phlu, a Chinatown in Bangkok, Thailand.