The Top Five Most Heartbreaking Movies

In a fit of insomnia the other night, I started thinking of the most heartbreaking and bittersweet movies I’ve seen. Because this is normal, right? Thinking about sad movies? What do other people think about in the middle of the night when they cannot sleep? I’m really curious.

I usually make random lists in my head, think about occurrences that happened where I should have said a witty phrase, or think about something interesting that happened to me that day and then I think hey, that would be a cool blog post. And then I write it down and I’m always disappointed. Oh, midnight thoughts, how you both intrigue and sadden me.

I suggest watching these if you want to become depressed for the rest of the night. Or if you want a good cry, because these will hit you right in the feels.

Dear Zachary: A Letter to a Son About His Father (2008)

Dear Zachary

I heard a lot of good reviews about this movie, so I watched it about six months ago. It left me feeling like I’ve been sucker-punched in the heart. It also got a 94% on Rotten Tomatoes.

Dear Zachary is a documentary written to Zachary, Andrew Bagby’s young son. You soon find out that Andrew, a young doctor, was found murdered in a park in Pennsylvania in 2001, and the key suspect is his ex-girlfriend. That ex-girlfriend then finds out she is carrying Andrew’s child – Zachary.

Andrew’s long-time friend, Kurt Kuenne, makes this documentary to show Zachary what an amazing man his father was, but the story soon turns ugly, focusing on Andrew’s conniving ex-girlfriend. It’s sort of like a murder mystery meets touching documentary all in one. The last half hour, though, will touch even the most heartless of souls.

This movie sparked a book titled Dance With The Devil: A Memoir of Murder and Loss, which was written by Andrew’s father, David. If the documentary was amazing, the book will probably be twice as good.

The Boy in the Striped Pajamas (2008)

The Boy in the Striped Pajamas

I always recommend that my friends this movie. It’s one of those movies that is just good, you know? The story starts off with a well-off German family whose father is a key player in the Nazi Party during World War II. The family moves to Poland and it happens that there is a concentration camp practically in their backyard.

Bruno, 8, the main character in the movie, meets Shmuel, a Jewish boy of the same age stuck on the other side of the fence. They form an unlikely friendship, one being a Nazi’s son and one being a Jewish captive, and similar to Dear Zachary, the last half hour of the movie is the most intense.

This movie was also based on a book written by John Boyne, a book I bought when I was studying abroad in Ireland. In my humble opinion, this was one of those instances when the movie was better.

I got the opportunity to study in Dublin for four months in 2012, and my friend Rose and I took a trip to Poland. We visited Auschwitz and Birkenau, two of the largest concentration camps in Poland. It really put things into perspective, and gave me another perspective into this movie.

The Wave (2008)

The Wave

Speaking of World War II, this movie follows a German high school teacher who teaches his class about autocracy (a system of government where one person is in power), and while his students don’t believe something like the system Hitler used could never happen again, the movie shows that sometimes we don’t always learn from our mistakes.

This movie is based on a real classroom experiment called the Third Wave, something teacher Ron Jones applied to his high school classroom in 1967. He created a slogan, a salute and a secret police force that his class had to pay order to.

According to Wikipedia, “the experiment was designed to explore the question of how it was that the people of Germany could allow the rise of Facism under National Socialism and claim ignorance of the atrocities that were committed by them to neighbors and friends.” Ron Jones’ experiment spiraled out of control, as can been seen in the film.

The last twenty minutes of this movie are indubitably the most intense. It left me feeling heartbroken.

Atonement (2007)


Atonement, based on a book written by Ian McEwan, stars Kiera Knightley and James McAvoy, as well as a young Saoirse Ronan. The word atonement means “satisfaction or reparation for a wrong or injury.”

In the movie, McEwan and Knightley’s characters secretly love each other but must keep it a secret. So, when Ronan’s character (Knightley’s younger sister) finds out, she accuses McEwan’s character for doing a terrible act – sexually abusing their younger cousin. But, McEwan’s character was innocent, something everyone finds out years later. It’s a story that spans six decades about love, betrayal and family struggles.

The Hunt (2012)

The Hunt

This movie is similar to Atonement, where the main character in the movie is accused of committing a crime he didn’t do. It takes place in a small Danish community with Mads Mikkelsen’s character working at a local kindergarten. A young schoolgirl who has a crush on him accuses him of exposing himself and matters are taken into the teachers and authorities hands.

Mikkelsen’s character is shunned by the community, as if going through a painful divorce and trying to rekindle his relationship with his son wasn’t enough. It also got a 93% on Rotten Tomatoes and won a ton of international awards. It is in Danish and has subtitles.