The 10 Most Heartbreaking Romantic Films of All Time

Romantic films do not always end well every time. As beautiful and great as they are in some moments, sometimes the story leads us to a very somber place toward the end of the film.

With that in mind, here is a selection of 10 amazing romantic films that are heartbreaking. As usual, many things interfere in the choice of the titles of an article like this, but as always, memory and personal preferences are the main factors.

The movies are not ranked, and if you think any other heartbreaking romantic film should be on this list, please leave it as a recommendation in the comments section below.

So, here are 10 great heartbreaking romantic (or not so romantic) movies:


10. The Broken Circle Breakdown (2012; dir. Felix Van Groeningen)

Written by Carl Joos and Felix Van Groeningen, based on a play by Johan Heldenbergh, and starring Didier Bontinck and Mieke Dobbels, “The Broken Circle Breakdown” is one of the most interesting European movies of the 2010s.

The movie follows the story of Elise (Veerle Baetens) and Didier (Johan Heldenbergh) over seven years. Because of their love for bluegrass music, they fall in love and after some time they have a daughter. But years later, after the death of their child from cancer, they experience an incident from which their relationship might never recover.

With great character arcs, and an amazing setting and dialogue, “The Broken Circle Breakdown” is definitely a great and very heartbreaking film that revolves around the romance between Elise and Didier.

With great acting and a great story, “The Broken Circle Breakdown” is a movie that every cinephile should check out.


9. Brokeback Mountain (2005; dir. Ang Lee)

Considered by the BBC as the 40th best film of the 21st century, “Brokeback Mountain” is Ang Lee’s masterpiece.

Starring Heath Ledger and Jake Gyllenhaal in amazing performances, “Brokeback Mountain” follows the secret love story of two cowboys over the years.

With great directing by Lee, this movie shows the complex and beautiful relationship between these two men and has one of the most heartbreaking endings of all time.

This film won the Golden Lion at the Venice Film Festival and was nominated for eight Academy Awards, winning Best Director, Best Adapted Screenplay and Best Original Score. The movie lost Best Picture to “Crash,” even though “Brokeback Mountain” definitely deserved the award.


8. Two Lovers (2008; dir. James Gray)

two lovers

James Gray is definitely one of the best and most underrated directors/screenwriters working today.

In “Two Lovers” we follow the story of Leonard Kraditor (Joaquin Phoenix), a man who helps his family in the dry cleaning business and is a photographer. After a suicide attempt, he meets two women. Sandra (Vinessa Shaw), is the daughter of a business associate of his family. Michelle (Gwyneth Paltrow), his neighbor, is a woman having an affair with a married man.

Divided between these two women, Leonard seems more interested in Michelle while Sandra tries to save him. With great dialogue and character arcs, and a very complex and also heartbreaking ending allied with the prodigious performance by Phoenix, “Two Lovers” is among the most intriguing romantic stories of this century.

Definitely a movie that every cinephile should check out.


7. Happiness (1965; dir. Agnès Varda)

Le bonheur

One of the most interesting works in the filmography of one of the most intriguing European filmmakers of all time, “Happiness” is a movie that should definitely be watched.

“Le Bonheur,” in the original title, follows the story of François (Jean-Claude Drouot), a married carpenter who lives happily with his wife Thérèse (Claire Drouot) and their children. One day he meets a woman in the local post office and starts to see her, something that will lead to a heartbreaking situation.

With great directing and writing by Agnès Varda, and a very heartbreaking ending, “Happiness” truly deserves to be among the best French films from the 1960s.


6. The Lovers on the Bridge (1991; dir. Leos Carax)


In his third feature film, Leos Carax told a story that takes place on Pont Neuf, Paris’ oldest bridge.

The movie follows Michèle (Juliette Binoche), a painter going blind and living on the street after a failed relationship, and Alex (Denis Lavant), a homeless performer who is addicted to sedatives and alcohol. As Michèle’s vision is deteriorating, she depends more and more on Alex. When they start to get their lives back on track, he becomes afraid she is going to leave him.

A very dreadful and tough story about life on the streets with brilliant performances by Binoche and Lavant. One of the best movies in Carax’s filmography.


5. Bitter Moon (1992; Roman Polanski)

bitter moon

From a romantic start to a very somber ending, “Bitter Moon” is without a doubt among Polanski’s greatest works.

The movie follows the story of Fiona (Kristin Scott Thomas) and Nigel (Hugh Grant), a British couple sailing to Istanbul. On this ship, Nigel meets Mimi (Emmanuelle Seigner), a French woman, and her husband Oscar (Peter Coyote), a paraplegic man who tells him their story.

With many nuances and astonishing performances by Seigner and Coyote, “Bitter Moon” is a very somber story about love, hate and obsession. Definitely a movie that should be checked out.


4. Damage (1992; dir. Louis Malle)

With an amazing script by David Hare based on Josephine Hart’s novel, “Damage” is one of the greatest films in the career of Louis Malle.

“Damage” follows the story of a member of the Parliament, Dr. Stephen Fleming (Jeremy Irons), who falls in love with Anna (Juliette Binoche), the fiancée of his son, and starts a romance with her, something that will have terrible consequences on his life.

Irons and Binoche deliver in this film some of the best performances of their career. With very realistic dialogue, this somber love story is a movie that without a doubt deserves a place on this list.

From the great setting of the film to the prodigious script, “Damage” is a movie that definitely should be checked out.


3. Romeo and Juliet (1968; dir. Franco Zeffirelli)

Romeo and Juliet (1968)

Of course Shakespeare would be here.

Probably the most well-known tragic love story of all time was adapted to the silver screen in 1968 by Italian director Franco Zeffirelli. Starring Leonard Whiting and Olivia Hussey, this is probably still the best film adaptation of Shakespeare’s play to date.

“Romeo and Juliet” follows the story of two families of Verona that have been fighting for years: the Capulets and the Montagues. But when Romeo Montague falls in love with Juliet Capulet, they will do everything to be together despite the feud between their families.

Having strong performances and great art directing, “Romeo and Juliet” is a great film and without it this article would not be complete.


2. The Pillow Book (1996; dir. Peter Greenaway)

The Pillow Book (1996)

Another great work by Peter Greenaway, “The Pillow Book” with its astonishing aesthetics is a film that definitely should be seen in Greenaway’s filmography.

Following the story of a Japanese model living in Hong Kong who is obsessed with books and writing on bodies, this woman tries to find a lover who has her same desire for carnal pleasure, and also her adoration for calligraphy and poetry.

With the very powerful imagery and perfect art directing we are able to see in Greenaway’s works, “The Pillow Book” is without a doubt one of the most complex and one of the best films in the director’s career.

This very unique atmosphere, allied with the great script based on Sei Shonagon’s diary of the same title, makes this a mandatory movie for any cinephile.


1. Revolutionary Road (2008; dir. Sam Mendes)

Revolutionary Road

I know this was already said about other actors in this article, but truly, Kate Winslet and Leonardo DiCaprio deliver in Sam Mendes’ “Revolutionary Road” some of the best and strongest performances of their career.

The movie follows a couple living in Connecticut in the 1950s. Although they seem to live a perfect life, they are unhappy. During the film, we see them trying to deal with their personal problems while they raise their children.

With a very realistic and tough approach on the life of these characters, “Revolutionary Road” is once again Mendes at his peak. With a very great adaptation from Richard Yates’ novel by Justin Haythe, this is one of the best scripts written for drama in the first decade of this century.

“Revolutionary Road” is one of the best films in Mendes’ career and a movie that definitely should be checked out.

Author bio: Vítor Guima is a filmmaker, writer and musician from São Paulo, Brazil. Every day he watches a movie, reads a few pages from a book, listens to an album and freaks out with the feeling of not having enough time to see everything. You can follow him on Instagram on @ovitorguima.