Films that will break your heart [over and over again].
As I'm going through a breakup, I decided to share some of my favorite films that will shred your heart into pieces.
There is nothing like a film that shamelessly rips your heart into a million pieces, leaving you to contemplate the meaning of life and love for hours after the credits role. This is my favorite kind of movie. The kind of movie that touches you in ways you didn’t think a story could, the kind that perfectly displays what it is to be human. What is it to have a heart, and what happens to you when that heart is broken?
While this is indeed my favorite kind of movie, I’m also a little inspired as I’m going through a heartbreak of my own. A moment of mourning past relationships, my past lives, and the comforts of home. Break-up. New city. 400 miles away from home. Heartbreak.
In celebration of my own, here are my top 5 favorite films about heartbreak (and if you aren’t heartbroken right now, these will make you feel it).
Important note: This article may contain some spoilers.
Blue Valentine (2010)
Directed by Derek Cianfrance, Blue Valentine follows two lost souls, in a nonlinear fashion, through their time together. Falling in love, falling out of love, and everything in between.
We meet Dean and Cindy, a married couple with a tension that you could cut with a knife (but not in a good way). The relationship is strained and they can’t seem to even be in the same room with each other without Cindy getting fed up with Dean, while Dean doesn’t seem to understand where Cindy’s frustrations come from.
The beautiful thing about this film is we then get to see flashbacks to the beginning of their relationship. They are both young, full of life and joy, and quickly fall deeply in love with each other. Cindy is in college to be a nurse with a douche of a jock boyfriend, and Dean works for a moving company just trying to make a living. While in two different social classes, there is just something about the other that draws them in. Their love is passionate, fun, and spontaneous.
But as we all know, time goes on, and people change. When we return to the present, we can see how these two people have changed and grown apart.
This a raw and honest portrayal of the timeless question, is it better to have loved and lost than to never have loved at all?
Not all romances end like a fairytale. That doesn’t mean the love wasn’t real.
Waves (2019)
Directed by Trey Edward Shults, Waves takes us through the turbulent journey of a suburban family who attempts to navigate love, loss, and grief.
This film deals with the love felt through familial and romantic relationships and the loss associated with it.
Tyler is a popular high school jock who lives with his upper-middle-class family but struggles with his relationship with his domineering father, who pushes him psychologically and physically to be the best wrestler he can be.
But he finds solace and release with his girlfriend Alexis, who makes him feel free. That special naive young love that you only get once. However, they are 17-year-olds who can find their relationship has their own bumps in the road.
And he finds acceptance with his younger sister, Emily. She seems to be the only person who truly understands him. But an unfathomable tragedy occurs (that you truly won’t expect - if you think you know where I’m going with this, trust me, you don’t), and tests the limits of what unconditional love is, and if it’s even possible.
And through all the tragedy, this film shows that new love can be found, too.
Waves is the sort of film that will rip your heart out and put it back together over and over and over again. Overall, you’ll leave feeling changed as a person but perhaps even have a little hope.
Brokeback Mountain (2005)
Ang Le, primarily known for Crouching Tiger, Hidden Dragon did something so special by bringing the beloved gay, rodeo cowboy flick, Brokeback Mountain, to life.
“I wish I knew how to quit you”.
The first (and only, blasphemy, I know) LGBTQIA+ film on the list! One of my favorite films about heartbreak, but also truly one of my favorite films in general. Jake Gyllenhaal and Heath Ledger embodied this film so well and so authentically that you forget you’re watching a narrative piece. The addition of melding the drama genre with neo-Western felt very innovative to me.
Enis and Jack. We’re set in Wyoming in 1963 (so you can only imagine how everyone feels about queer…) and find these two cowboys hired to herd sheep through the summer. And it doesn’t take long for Enis and Jack to find comfort in each other while struggling with the societal sin of homosexuality. But all summer romances come to an end eventually, don’t they?
The two settle down, separately, with their wives and their children. But that doesn’t stop the two of them from meeting from time to time and, you guessed it, Brokeback Mountain.
Queer love, especially in period pieces, always breaks my heart. To love someone so desperately, even though you and the majority of the world think it to be wrong, that nothing can keep you apart.
While there are many complications with their relationship (duh), this film, to me, embodies what true love is and how it feels. But do not be mistaken; it’ll break your heart over and over again.
Eternal Sunshine of the Spotless Mind (2004)
Is a list of the most heartbreaking films complete without a shoutout to Eternal Sunshine of the Spotless Mind? Directed by Michel Gondry, this film has become a timeless classic, and its popularity seems to only grow with time. Another beautiful example of meshing drama with another genre, this time being science fiction. My favorite type of science fiction - modern and subtle.
Joel and Clementine are two lovers who, after a break-up, both decide to remove the other from their memories.
What’s tragic about this film is that these two characters deeply feel like they have nothing in common and are potentially not as compatible as they’d wish to me. But, I would entirely disagree.
Joel and Clementine are both cynical/realists who feel misunderstood. And it’s through that connection that I do think, on a deeper level, they do understand each other. Which is why they both fight tirelessly to find each other again in their memories while they’re simultaneously being erased.
The question remains - will they be too late? This film comes with all sorts of twists, turns, and really fun sci-fi elements. But it also has that deep, melancholic sense of yearning that can be intoxicating and heartbreaking all at the same time. To miss someone who isn’t actually gone.
Lost in Translation (2003) / her (2013)
To finish this list off, I had to include one of my ‘Roman Empire’s - the crossover of Lost in Translation, directed by Sofia Coppola, and Her, directed by Spike Jonze.
First, let’s get into the films.
Lost in Translation follows Charlotte, an American, who is staying in Japan with her husband, who is a celebrity photographer, and Bob Harris, who is a washed-up American movie star who is in Japan to do advertisements. Both of these characters run into each other at this hotel many times, and they share a deep sense of loneliness, stagnancy, and unsure of their place in the world.
Charlotte is often alone in the hotel while her husband is off working, and seemingly pays no attention to her. This has her contemplating their relationship and mostly, not knowing who she wants to be, because it’s obvious this isn’t it.
As we join these two on their contemplative journeys, we witness a bond forming that is hard to differentiate between platonic and romantic. Regardless of the relationship, I think that they find a special kind of love and comfort in each other while they navigate their views on themselves, and their lives while also being ‘stuck’ in a country where they can’t even speak the language.
Her is another fun, heartbreaking tale that dips its toe into the sci-fi genre. Set in the not-so-distant future, we find our protagonist, Theodore, amid a divorce from the love of his life while falling in love with his AI assistant, Samantha.
Aside from the existential crisis I feel at the idea of falling in love with AI, and I’m sure many already have, Theodore has many of the same issues that Charlotte from Lost in Translation has. He feels a sort of isolation and loneliness, which I’m sure is typical during a divorce. And he finds love and comfort in someone (or something) that is unconventional.
This film shows that love has no bounds, and also that one of human beings most basic needs is love. I’m sure there is science behind it that I have not bothered to investigate, but all of these characters, are deeply lonely or have a fear of it.
Can we appreciate love, even when it’s lost?
Sofia Coppola + Spike Jonze
Here is where things get interesting. One of the most beautiful things about film is that we get to see a small peek into the mind of the writer or the director. As a writer myself, my work is heavily influenced by my own personal experiences, and these two directors are no different.
Coppola and Jonze were married from 1999 to 2003. It is rumored that the husband in Lost in Translation is based on Jonze and their marriage. Is this speculation? Of course it is. It is also said that the film her could be a response or even a letter back to her.
If all of these things are true, it is fascinating to see how these directors can express themselves and their views on love and how we can perhaps speak to one another through film.
This article became a lot longer than I anticipated, but it’s hard to narrow this idea down into a top 5 list, as there are so many more. The list of films that will break your heart is endless.