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5 best breakup movies, ranked

After a particularly painful breakup, it’s expected for those involved to turn to some common remedies – friends, comfort food, sad music, and of course, tear-jerking films. The best breakup movies are often the saddest and can reflect the heartache that viewers are feeling. Whether watching with friends or alone in a cozy bed, these films can offer some much-needed catharsis after a nasty breakup.

From beloved and often misunderstood classics to honest portrayals of messy separations, sad breakup movies can be exactly what some viewers need to ease their sorrow. Whether audiences are mending a broken heart or just in the mood for some emotional exploration, these profound stories of love, loss, and self-discovery are fan-favorite flicks that have cemented their place in cinematic history.

5. 500 Days of Summer (2009)

Joseph Gordon-Leavitt and Zooey Deschanel in 500 Days of Summer.
Fox Searchlight Pictures

Every millennial knows the often misinterpreted romantic drama 500 Days of Summer, a film that would define the early 2010s. Directed by Marc Webb, the movie tells the story of hopeless romantic Tom Hansen (The Dark Knight Rises star Joseph Gordon-Levitt) as he reflects on the 500 days he spent with his now ex-girlfriend, Summer Finn (Zooey Deschanel).

The film depicts Tom’s changing perspective of their relationship, with split screens showing the version of the story without the protagonist’s rose-colored glasses. It’s also often credited with perfecting the “manic pixie dream girl” trope, which would soon lead to insightful discussions about why viewers tended to think of Summer as the antagonist when it was Tom’s obsession with an unrealistic fantasy that caused him to miss troubling signs in the relationship. This complexity makes 500 Days an endlessly rewatchable breakup movie, as its message tends to change depending on who’s watching it.

4. Forgetting Sarah Marshall (2008)

Jonah Hill, Mila Kunis, Jason Segel, Russell Brand, and Kristen Bell in Forgetting Sarah Marshall on Hulu
Universal Pictures

For those who want their sad breakup movie to have a splash of comedy, director Nicholas Stoller’s Forgetting Sarah Marshall is the perfect pick. Starring Jason Segel as down-on-his-luck musician Peter Bretter and Kristen Bell as rising TV star Sarah Marshall, the film portrays their abrupt separation after five years together. In an effort to move on, Peter goes on a trip to Hawaii, but unfortunately runs into Sarah and her new boyfriend, British rock star Aldous Snow (Russell Brand). Meanwhile, Peter almost gives up on the obvious connection he forms with the endearing front desk clerk Rachel Jansen (Mila Kunis).

The story seems obvious and the clichés are hard to miss, but Forgetting Sarah Marshall has somehow kept its timeless charm as a cheesy, sweet, and undeniably hilarious breakup movie. Viewers who are in the mood for a roller coaster of emotions that leads to a happy ending won’t go wrong with this one.

3. La La Land (2016)

Ryan Gosling and Emma Stone looking at each other in the cinema in La La Land.

La La Land is a romantic musical movie that made audiences leave cinemas in tears when it first premiered. Directed by Damien Chazelle, it tells the story of struggling jazz pianist Sebastian “Seb” Wilder (Ryan Gosling) and aspiring actress Mia Dolan (Emma Stone), who form an instant connection when they first meet and then decide to pursue their dreams together in Los Angeles. However, things don’t go according to plan when they realize their paths may no longer align.

With a now-iconic score composed and orchestrated by Justin Hurwitz, a heart-wrenching and realistic story, and fantastic performances from Gosling and Stone, La La Land unsurprisingly became a global sensation that would go on to receive numerous accolades. Its raw and emotional depiction of two people who love each other, but just can’t be together resonated with viewers who understand that hard decisions can often make or break long-term relationships.

2. Marriage Story (2019)

Scarlett Johansson and Adam Driver in their living room in Marriage Story.

Scarlett Johansson and Adam Driver star as Nicole and Charlie Barber in director Noah Baumbach’s Marriage Story, one of the saddest and best romance movies on Netflix to date. The film explores their failing marriage, which eventually leads to a messy divorce. With their lawyers, in-laws, friends, and young son involved, the situation just gets more complicated as issues from their past rise to the surface.

The award-winning film received recognition for powerful performances from Johansson and Driver, whose chemistry and explosive interactions made the entire movie gripping. Marriage Story thoughtfully delves into the threads that make up a mature relationship, and which ones eventually cause it to unravel. In the end, it becomes a poignant mix of heartache, love, and regret, especially after Charlie finds the note Nicole wrote about him so many years ago.

1. Eternal Sunshine of the Spotless Mind (2004)

Clementine and Joel laying in bed in Eternal Sunshine of the Spotless Mind
Focus Features

When Clementine Kruczynski (Kate Winslet) goes through a devastating breakup, she decides to use the services of New York City firm Lacuna to erase her memories of her past relationship completely. This shocks and frustrates her ex-boyfriend, Joel Barish (Jim Carrey), who decides to have the same procedure, but regrets it when it’s all too late.

Eternal Sunshine of the Spotless Mind, directed by Michel Gondry, is told in a nonlinear fashion, with Joel and Clementine seemingly initially meeting on a train for the first time. Their strong connection hints at emotions that any scientific process could not totally remove, and as they rediscover their relationship, they realize why they were and are doomed to break up again – and still, they decide to give it another chance.

A beloved cult classic, Eternal Sunshine would go on to become not just a quintessential breakup film, but also one of the best sci-fi movies of the 2000s. Its incorporation of sci-fi and even fantasy elements bolster its heartrending narrative about two people with clashing personalities who keep falling in love even when they’re bound to fall apart.

Hannah Saab
Saab whips up SEO-optimized articles as a writer for Digital Trends and updates top-performing articles on Collider.
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