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Most Heartbreaking Movies Playlist


Welcoming the month of romance and mushy inseparable couples, we’re deviating from the cliché route and instead, we’re going to be exploring the world of heartbreaks and devastation; so sit back, relax and bask in the melancholia. 

  1. Titanic

Commencing our list with one of the highest grossing movies of all time, many of you saw this Steven Spielberg film coming. Inspired by the events of a tragic true story, Titanic depicts the tale of two star-crossed lovers who are separated by the social principles of status and wealth. Jack Dawson, a poverty-stricken young man who receives tickets to board the ‘unsinkable’ RMS Titanic by sheer luck and Rose DeWitt Bukater, a wealthy maiden who is desperate to escape the shackles of her high social standing, fatefully meet on a deck where Rose plans on committing suicide due to the stress resulting from her arrogant fiancé, Caledon Hockley. Jack manages to save her in time and thus, their fates are entwined and they eventually fall in love with each other. 

Unfortunately, just when their seed of romance was budding, the RMS Titanic collided with a gargantuan iceberg and began it’s descend down to the bottomless ocean. Desperate to live, Jack and Rose overcame many obstacles together but in the end, Jack fails to survive and regrettably dies of hypothermia; leaving Rose all alone. Rose cites that she’ll never let go of the memories that they shared together and promises to live on without any regrets. In remembrance of his legacy, she adopts Jack’s surname and lives under the name of Rose Dawson. 


2. Brokeback Mountain

Unlike any other romance film, Brokeback Mountain is an American romantic drama film that depicts the story of two adult cowboys who have both unknowingly fallen in love with one another. Ennis Del Mar and Jack Twist first meet in the summer of 1963; both hired to herd sheep on the Wyoming mountains. They initially started off as workmates and drinking buddies but after one fateful night, a drunk Jack makes sexual advances towards Ennis, who is reluctant but eventually responds to Jack’s actions. The next morning, Ennis claims that it was a one-time incident but the both of them have already fostered an emotional relationship. After the summer ends, the two men go their separate ways. Fast forward a few years, they eventually marry other women and have developed loving families. 

Despite this, Ennis and Jack still decide to meet each other through inconstant fishing trips. Torn between the issue of homosexuality and it’s consequences, Ennis is refuses to accept Jack’s offer of living together. Through the course of time, not only do their relationships with their wives worsen, but the both men have their fair share of ups-and-downs in their interactions as well. Some time later, it is revealed that Jack had passed away after a tragic accident; leaving Ennis in despair. In the end, it is shown that Ennis keeps a few of Jack’s clothes and a postcard of Brokeback mountain in his closet; forever to be remembered. 


3. City of Angels

Just as it’s title suggests, in an universe where Angels are real, Seth, who is one of the many Angels, is mainly tasked to guide those facing death to the afterlife. Being an Angel, Seth does not require any food or water to survive, invincible to mere human and is immune to the sense of touch; thus making him immortal and somewhat emotionless. One day, while waiting for a man to kick the bucket during a heart surgery, he is astonished by the efforts of surgeon Maggie Rice; trying to save the dying man’s life. Intrigued by her, Seth trails her and makes himself visible to her; in order to understand her persona better. Mesmerised by her, Seth can’t stop thinking about her and Maggie is attracted to his peculiar attitude as well. 

One day, while monitoring an ill man in a hospital, Seth is utterly shocked when the man, Nathaniel Messinger, can sense his presence and is even aware of his job. Curious to obtain answers, Seth makes himself visible to him and Nathaniel reveals that he was once an Angel but willingly chose to became human by the act of “falling”. In order to be together with Maggie, Seth jumps down a tall building and to his glee, he becomes a human; feeling all kinds of emotions and sensations. He immediately looks for Maggie and realising Seth is a human, they passionately make love to each other. Barely a day later, their bliss is cut short as Maggie is involved in an accident and unfortunately dies in Seth’s arms. As Seth grieves, Cassiel, his Angel comforts him and asks him whether he would still choose to become a human even if he knew that this would happen. Seth replies that: "I would rather have had one breath of her hair, one kiss of her mouth, one touch of her hand, than eternity without it. Just one.”


4. Hachi: A Dog’s Tale (Hachiko)

Based on an inspiring true story and a remake to the original Japanese film (Hachiko Monogatari), Hachiko tells the tale of the bond of owner, Professor Parker Wilson and his pet dog, Hachi. Initially finding Hachi at a train station, Parker decides to take him home until his original owner has been found. Parker’s wife, Cate, is very reluctant to keep Hachi and is upset at his presence. However, after a string of unprecedented events, Parker and Hachi develop a strong bond. Realising the extent of their relationship, Cate finally accepts Hachi into the family. 

Every day without fail, Hachi would follow Parker to the station in the morning and would once again come back in the evening to fetch his master. One day, Hachi refuses to follow Parker to work and barks in disapproval at him. Not wanting to be tardy, Parker leaves Hachi behind and proceeds to work. At work, Parker experiences a sudden heart attack and unfortunately dies. Unknowing of his master’s condition, Hachi waits for Parker to come back after work but to no avail; he is nowhere to be seen. Even after Parker’s relatives and friends have tried to convince Hachi that he is no longer coming back, Hachi still remains firmly loyal and continues waiting for an astonishing nine years. In the end, Hachi dies at the fated station all alone in the snow; still waiting for his beloved master. 

5. A Walk to Remember

Adapted from Nicholas Spark’s novel of the same title, A Walk to Remember is a story about a teenage delinquent, Landon Carter, who is the epitome of a rebel. After Landon gets caught for underage drinking and harming another student, he is threatened with expulsion but is given a chance to redeem himself by tutoring other students and joining the school play; he chooses the latter. During these events, he meets Jamie Sullivan, a shy girl whom he had attended kindergarden together with. When Landon was having a difficult time in memorising the script, Jamie offered to help him on one condition: he was not allowed to fall in love with her. Landon quickly dismisses this as a silly statement. However, as time passes, they begin to develop a more intimate relationship.

As the long-awaited play arrives, Jamie shocks both Landon and the audience with her beautiful voice. Since then, Landon becomes completely mesmerised by her and after a few conflicts, they soon began dating. However, much to Landon’s dismay, Jamie soon reveals that she has leukaemia and her treatment has not been going well. Landon, desperate to save Jamie, tries every single method possible to help her and eventually proposes to Jamie; to which she happily accepts. In the end, they successful get married and spend their last summer together; deeply in love. Jamie regrettably dies by the end of summer; leaving Landon longing for her love once more. 


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