ByDavid Burgos Pasol, writer at
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David Burgos Pasol

With Valentine’s Day around the corner, why not take a look back on your current and/or past loves and cherish the moments you shared? …or not. Movies are a perfect example of art imitating life imitating art and sometimes, they get it right when it comes to love - even with the heartbreak that comes along with it. Not everything in life is always going to be perfect and have a happy ending. So let’s focus on my top five movies that I feel portray what love and heartbreak is all about.

500 Days of Summer

Joseph Gordon-Levitt and Zooey Deschanel play a believable couple that gives viewers a range of emotions as you look at their relationship from the beginning to the saddening end. I think most viewers can place themselves in either of their shoes - as the person who’s pursuing the other or the one breaking hearts. This itself makes the movie relatable, as you feel for Gordon-Levitt’s character and his longing to be with Deschanel, while also understanding her character in that maybe, just maybe, two people won’t always work out the way you want them to.

Heartbreaking scene: When Gordon-Levitt comes to Deschanel’s party, believing this could be yet another chance at their romance - only to see she’s wearing an engagement ring. You're left just as surprised and confused as he is. In other words: WTF?

William Shakespeare’s Romeo and Juliet

Before you groan about why I’ve added this well-known Shakespeare tragedy, I have two words: Baz Luhrmann. I watched this in theaters when I was younger and could only think about what a beautiful job Luhrmann did to modernize this play. The soundtrack was also unbelievable as it enhanced the emotions the actors conveyed throughout the film. While everyone is familiar with the story, Luhrmann added guns rather than swords, cars instead of horses, all the while maintaining Shakespearean dialogue, making this an unforgettable tragedy.

Heartbreaking scene: When Juliet barely wakes up from her sleep-induced poison to find Romeo drinking out of the vial that ends his life. Her sobbing alone will make you tear up.

In the Mood For Love

A classic period film taking place in 1960s Hong Kong, Chow (played by the handsome Tony Leung) and Su (the exquisite Maggie Cheung) are both married and suspect their spouses are having an affair with one another. They start a platonic friendship and both role-play on how to confront their cheating spouses. As Chow and Su spend more time together, their love for one another is evident, yet unable to take it a step further as they don’t want to stoop to the same level as their spouses.

One of my favorite films, In the Mood for Love can be a bit slow, but that’s the beauty of the film. Wong Kar-Wai’s style slowly builds on Chow’s and Su’s love throughout the movie, similar to a slow dance between the two. You’re rooting for both to leave their spouses and spend the remainder of their days together. Plus, they look absolutely perfect together.

Heartbreaking scene: While having dinner with his friend, Chow discusses an old tradition that when a person had a secret that couldn’t be shared, he would go to the top of a mountain, make a hole in a tree, whisper his secret into the hole and then cover it with mud.

Chow does exactly this a couple of years later while visiting Angkor Wat in Cambodia. He whispers for some time into a hole in a ruined wall, before filling it with mud. The viewer doesn’t know exactly what was said but you can only imagine it had something to do with his love for Su. Please pick up the broken pieces of my heart now.

Fun fact: Wong Kar-Wai is one of Sofia Coppola’s inspirations and you can see the same themes spread out throughout her film, Lost in Translation, especially in the final scenes as Bill Murray whispers something into Scarlett Johansson’s ear. Coppola thanked Kar-Wai and several other directors as she accepted her Best Original Screenplay for Lost in Translation at the 2004 76th Annual Academy Awards.

Lost in Translation

Of course I had to add this here following the last film on my list! Lost in Translation follows Bob (Bill Murray), an American movie star going through a midlife crisis and Charlotte (Scarlett Johansson), a young woman who followed her husband to Tokyo from New York, yet feels detached to him and his lifestyle. Sofia Coppola (who was nominated for Best Director and won the Best Original Screenplay Oscar) did an amazing job of showcasing Bob's and Charlotte's bond between each other. You watch them go on multiple innocent dates, knowing nothing can go further than that, but still want them to run off together.

Heartbreaking scene: Bob, on his way to the airport to head back to the United States, catches Charlotte on the streets of Tokyo. He jumps out of his vehicle to catch up with Charlotte, hugs her and whispers something in her ear, as she sheds tears. The viewer will never know what Bob said and that’s the heartbreaking beauty of it.

Eternal Sunshine of the Spotless Mind

Written by Charlie Kaufman and directed by the amazing Michel Gondry, this film can be described as a romantic science-fiction comedy-drama. The film revolves around Joel (played by Jim Carrey) and Clementine (Kate Winslet) who seem to hit it off in New York. They then realize that they were former lovers who had their memories of each other erased. The beauty of this film is that it gives viewers a glimpse of a failed relationship through the eyes of Joel as he goes through the process of erasing his memories of Clementine. Starting from his most recent memory (and worst fight) with Clementine, the film progresses in a very non-linear fashion to a time when Joel remembers why he fell in love with Clementine. The more memories he “sees” of Clementine being erased, the more Joel realizes he doesn’t want to forget her.

Without the sci-fi elements mixed into the film, it really gives a believable look at relationships as a whole - the good, the bad and the ugly. We’ve all been there before with current and past loves - the fights, the break-ups and the make-ups. Kaufman and Gondry cleverly mix everything a relationship is all about and gives the viewer a dose of reality, especially when dealing with a gut-wrenching break-up.

Heartbreaking scene: As Joel’s “final” memory of Clementine is being erased in his head, he describes the way he felt meeting her for the first time, as the house they're in crumbles apart (a sign that the erasure is in process). The scene ends with Joel telling her he loves her while she slowly whispers to him to meet her in Montauk. Why do you continue to play with my heart strings, Gondry?

These are my top five “heartbreaking” movies. What are some of yours and why? Let me know in the comments below!


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