10 Saddest Movie Breakup Scenes

La La Land

Starring: Ryan Gosling and Emma Stone

La La Land is one of the rare films that somehow manages to equally be the happiest things you have ever seen as well as the saddest.

The ending — where the audience literally has to watch both characters imagine what their lives had been like if they had stayed together — is one of the most emotionally brutal movie scenes ever filmed.

(500) Days of Summer

Starring: Joseph Gordon-Levitt and Zooey Deschanel

(500) Days of Summer is not just a movie with a break-up, it's a movie all about a break-up.

Rather than telling the story from beginning to end, however, the film jumps around and tells it out of order.

It also invokes the painful trope of one person wanting to be friends after the romantic relationship is over, which completely devastates the other.

The Break-Up

Starring: Jennifer Aniston and Vince Vaughn

Much like (500) Days of Summer, The Break-Up is more about the end of a relationship, but it is a touch more light-hearted in its execution.

It's also different in that both people in this relationship are still in love with the other, which makes it more painful when they begin treating each other badly afterwards.

High Fidelity

Starring: John Cusack, Iben Hjejle, Jack Black, Todd Louiso and Lisa Bonet

High Fidelity is one of the most classic romance-gone-bad stories ever told, and the film is based on a novel of the same name.

It is less about one relationship, however, and more about the many relationships that the main character Rob Gordon (played by the incomparable John Cusack) has been in.

Gordon suffers another failed relationship and tries to figure out where all the rest went wrong, which takes the viewer down a path of seemingly limitless pain.

Eternal Sunshine of the Spotless Mind

Starring: Jim Carrey, Kate Winslet, Kirsten Dunst, Mark Ruffalo, Elijah Wood and Tom Wilkinson

While all of the movies on this list have moments and scenes that are grounded in some sense of reality, Eternal Sunshine of the Spotless Mind is the only one that uses partial science-fiction and still manages to break your heart.

The revelation that two lovers are also former lovers who both separately underwent a process to forgot the other is just about as painful as it gets.

Closer

Starring: Julia Roberts, Jude Law, Natalie Portman and Clive Owen

Closer was a 2004 film about two couples whose lives became entangled after one person form each side cheated with one another.

It has what may be the most brutally honest admission of infidelity ever written in a script, which was so intense that it even influenced lyrics in a Fall Out Boy song.

Forgetting Sarah Marshall

Starring Jason Segel, Kristen Bell, Mila Kunis and Russell Brand

While Forgetting Sarah Marshall is definitely a comedy, it does have one of the saddest break-up scenes ever shot.

Unlike the other films on the list, however, sad is used here to represent "pathetic" rather than being actually sad.

It happens right at the very beginning of the film when Kristen Bell's character dumps Jason Segel's character while he is 100% naked. The whole thing is not for the faint of heart.

(Honorable mention: When Kristen Bell's character breaks up with Russell Brand's character and does a mean impression of him.)

Breakfast at Tiffany’s

Starring Audrey Hepburn, George Peppard, Patricia Neal, Buddy Ebsen, Martin Balsam and Mickey Rooney

While Breakfast at Tiffany's is certainly not a "break-up" movie, it does feature the main character being broken-up with in a pretty harsh way.

Hepburn's Holly Golightly is told off in a heartbreaking piece of dialogue by her fiancé.

"You call yourself a free spirit, a 'wild thing,' and you're terrified somebody's gonna stick you in a cage. Well baby, you're already in that cage. You built it yourself. And it's not bounded in the west by Tulip, Texas, or in the east by Somali-land. It's wherever you go. Because no matter where you run, you just end up running into yourself," he tells her.

The Wedding Singer

Starring: Adam Sandler, Drew Barrymore, and Christine Taylor

The Wedding Singer's entire plot hinges on the fact that the main character (played by Adam Sandler) gets dumped at the beginning of the movie.

It send him spiralling down a hole of depression that sees him start to lose gigs and push people away. It does ultimately all work out in the end, though, as this is a comedy.

The Last Kiss

Starring: Zach Braff, Jacinda Barrett, Casey Affleck and Rachel Bilson

The Last Kiss is not a movie you will find on many lists, as it was not a critical or financial success, per say, when it was released in 2006.

However, the storyline that follows Zach Braff's and Jacinda Barrett's characters through impending parenthood, inevitable cheating, and the comparison that their "last romantic kiss" was like a death is so emotionally annihilating that it is almost impressive.