In honor of Valentine’s Day, here are some of the best movies about heartache, because no one should be alone in their misery.
Honorable mention: “Titanic” (1997)
“Titanic” details Jack and Rose’s exhilarating romance that is cut short when the Titanic strikes the infamous iceberg. A poor, artistic boy falling in love with a rich girl betrothed to another is a recipe for disaster if I’ve ever heard one.
Honestly, it felt wrong to exclude this classic heartbreak from the list. Mythbusters proved the door would have sunk if they both tried to float on it, so I don’t care what the cynics say about “they both could have fit.”
The film is a little over three hours long, so make sure you have a free afternoon, but it can be streamed on Netflix.
10: “Me Before You” (2016)
“Me Before You” is about a quirky young woman, Louisa (Emilia Clarke), who becomes a caretaker for Will Traynor (Sam Claflin), a wealthy young man who was paralyzed from the neck down after being hit by a motorcycle. The two begin an unlikely relationship as Louisa tries to show Will that life is still worth living.
Last, but certainly not least, this movie is devastating and will leave viewers wondering what it means to love someone. It’s just under two hours and can be streamed on Prime Video with an MGM+ subscription or rented for $5.99.
9: “Someone Great” (2019)
After dating for nearly a decade, Jenny (Gina Rodriguez) and her boyfriend break up when she lands her dream job and has to move from New York City to San Francisco. Jenny leans on her two best friends to navigate the immediate aftermath of sadness and confusion as they have one last adventure together.
More than just a breakup film, this movie is about the everlasting bond of girlhood and friendship. It’s the perfect mix of heartbreak and fun.
The movie is 90 minutes long and can be streamed on Netflix.
8: “La La Land” (2016)
“La La Land” is a musical that details the passionate relationship between Mia (Emma Stone) and Sebastian (Ryan Gosling) as they work to balance their career ambitions with their love for each other. This film begs its audience to ask, “Is love enough?”
The film is exceptionally cinematic, with a stellar soundtrack, breathtaking shots of the L.A. skyline, lively dance numbers and an ending that’s sure to bring a tear or two. It’s a little over two hours long and can be streamed on Sling TV or rented for $3.99 on Prime Video.
7: “5 Centimeters per Second” (2007)
This anime is about two childhood best friends, Takaki (Kenji Mizuhashi) and Akari (Yoshimi Kondou), who try to remain in touch despite distance but eventually lose contact after high school. Their connection is undeniable, as if they are meant to be together.
This movie is incredibly moving and painfully realistic, reminding viewers that what’s meant to be is not always what is.
It’s only an hour long and can be streamed on Netflix.
6: “A Star Is Born” (2018)
“A Star Is Born” is about successful, but troubled musician Jackson Maine (Bradley Cooper) and struggling singer Ally’s (Lady Gaga) relationship with each other, themselves and fame. Gaga and Cooper earned their Oscar nominations (and the Oscar itself, in my opinion) with their poignant depictions of life, love and loss.
This film has the most devastating ending possible, I mean sobbing through the end credits, so prepare for that. It’s a little over two hours long and can be rented for $3.99 on Amazon Prime.
5: “(500) Days of Summer” (2009)
The ultimate situationship before the term “situationship” was even coined. In the movie, Tom (Joseph Gordon-Levitt) and Summer (Zooey Deschanel) meet at work before quickly growing close, blurring the lines between friendship and relationship. Tom is hopelessly in love, and Summer isn’t looking for a serious relationship, what could go wrong?
Listen, I’ve been a Summer, and I’ve been a Tom, and either way, this movie is a painful watch. Rather than a tale of right vs. wrong, this movie explores the idea of what is vs. what isn’t meant for you. It’s about 90 minutes and can be streamed on Hulu.
4: “Past Lives” (2023)
“Past Lives” follows the lives of childhood sweethearts who are separated when Na Young, a.k.a. Nora, (Greta Lee) immigrates to America until they reunite in New York City for a week, 20 years later. Upon reunion, Nora is married, but her connection with Hae Sung (Teo Yoo) is apparent.
The film focuses on “in-yun,” a Korean concept that believes people are deeply connected by fate and a multitude of previous lifetimes. The writer of the film, Celine Song, does a great job capturing the longing and “what ifs” present in each interaction.
The movie is an hour and 45 minutes long, and can be streamed on HBO Max. Also, about half of the movie is in Korean, so be prepared to read a little.
3: “We Live in Time” (2024)
Another non-linear plot, “We Live in Time” forces viewers to reckon with the limits of time and love as Almut (Florence Pugh) and Tobias (Andrew Garfield) fall in love before receiving news that threatens to wreck the life they’ve built with each other.
I quite literally cried for at least an hour of this one hour and 48-minute film, from beginning to end. The plot manages to inspire while simultaneously tearing your heart out of your chest. It can be watched on HBO Max.
2: “Eternal Sunshine of the Spotless Mind” (2004)
This film tracks Joel (Jim Carrey) and Clementine’s (Kate Winslet) relationship, from the excitement of meeting to the ache of breaking up, an ache that drives both to erase all their memories of the relationship.
The plot can be a little confusing the first and second watch due to the nonlinear storytelling, but it’s hard to miss the film’s essence: there are two flawed people who are trying to learn to love and receive love from others. This movie is sure to leave any viewer with a desperate longing for something they may not remember.
The movie is an hour and 45 minutes and can be rented on Prime Video for $3.99.
1: “Marriage Story” (2019)
“Marriage Story” explores the complicated and tense relationship between a couple going through a divorce and learning how to co-parent their son. Nicole (Scarlett Johansson) and Charlie (Adam Driver) perfectly execute the anger, love, resentment and care that boil into many explosive arguments.
The movie’s ideal soundtrack is just a loop of Taylor Swift’s ‘My Tears Ricochet,’ which painfully illustrates what it means to be ripped apart by the person you once trusted the most. Coming in at just over two hours, this movie can be streamed on Netflix.
The cover of LaLa Land. Picture by Netflix.