We independently assess all our recommendations. Purchases through our links may earn us a commission.
Whether the filmmakers drop you into the beginning, middle, or end of a relationship’s dissolution, it doesn’t matter where you start in these sad breakup movies; the result is the same – the romance is dissipating, and the tears are flowing. These films range from Oscar-nominated masterpieces to lesser-known heartbreak stories, but they all share one thing in common: the ability to create an atmosphere where audiences grieve the loss of a relationship just as much as the fictional characters involved.
1. 6 Years (2015)
A common thread among young love is the divergence of paths, which often leads to emotional breakups. 6 Years features Taissa Farmiga and Ben Rosenfield as Melanie and Dan, college students whose romance begins to unravel after a six-year relationship turns toxic. Although this film earned a respectable reception from critics, audiences weren’t as impressed with this portrayal of romance.
6 Years is a film about first love and how excruciating it can be to let it go. Mel and Dan experience both highs and lows as their journey begins to separate. They struggle to let go despite moments of unfaithfulness and violence. For anyone who has experienced first love and the pain of losing it through or after college, this film will hit you right in the ugly cry zone.
2. The Break-Up (2006)
Baited with comedy but guaranteed to hook you with the ugly cry, The Break-Up offers a realistic look at a very common type of breakup. Following a blow-out breakup, Brooke (Jennifer Aniston) and Gary (Vince Vaughn) plot to keep the condo they jointly purchased from each other, escalating their tactics as the movie progresses.
The death of this relationship forces out the deepest ugly cry, as this couple desperately hopes the other will change in ways necessary to salvage their relationship. Aniston and Vaughn have it out in the most honest and realistic way, mirroring what many couples go through after becoming comfortable in a long-term relationship. If you’ve been through this type of breakup, The Break-Up should be essential viewing.
3. Someone Great (2019)
After a bold career move forces a devastating breakup for Jenny (Gina Rodriguez), her best friends band together to spend one more epic night in New York before their lives change forever. In a heartfelt story about loss and growth, Jenny must relive the best and worst moments of her almost-decade-long relationship with Nate (LaKeith Stanfield). The series of flashbacks are devastating in many ways.
While Rodriguez is the driving force of the movie, she is joined by Brittany Snow and DeWanda Wise, who bring friendship and the art of letting go to the viewers. Netflix’s Someone Great elicits the deepest ugly cry from anyone fresh from an intense breakup.
4. The Best of Me (2014)
There had to be one Nicholas Sparks movie adaptation on this list, even though (arguably) they all follow the same formula. Former high school sweethearts Amanda (Michelle Monaghan) and Dawson (James Marsden) reunite decades later in their small southern hometown after the death of a mutual friend.
Definitely detested by critics (as most Sparks movies are), The Best of Me is a double-whammy breakup film as young Amanda (Liana Liberato) and Dawson (Luke Bracey) inevitably break up under devastating circumstances and, like the standard Sparks genre, are unable to be together later in life. The romance film pulls the ugly cry out, particularly when Monaghan and Marsden take the screen for the late second/early third-act breakup, Amanda sobbing, “I wanted you to hold me.” If you’re the type to stomach a Sparks adaptation that’s not The Notebook, The Best of Me is the perfect pick.
5. 500 Days of Summer (2009)
An iconic rom-com that any millennial will know, 500 Days of Summer tells the story of Tom (Joseph Gordon-Levitt), whose sudden breakup causes him to reflect on the time he spent with his now ex-girlfriend, Summer (Zooey Deschanel). As Tom’s bitterness influences his once-rosy memories, their love story takes on a different shade.
By the way!
Did you know we’re launching a Kickstarter campaign? In the next few months, our campaign for ‘Gentle Jack: The Party Game for Bad Friends‘ goes live! Visit the official website or follow the Kickstarter page to stay in the loop.
500 Days of Summer uses nonlinear storytelling to paint a complete portrait of the failing relationship between Tom and Summer. The movie is often credited with the “manic pixie dream girl” trope, which was misunderstood for quite some time. While it may not drive most viewers to tears, its nostalgia and the undertone of frustration and anger will be relatable for anyone going through a sudden breakup.
6. The Worst Person in the World (2021)
Aside from being one of the best coming-of-age movies for more mature viewers, The Worst Person in the World also makes for a fantastic unconventional breakup movie. It revolves around Julie (Renate Reinsve), who starts as a 20-something medical student in a relationship with a much older man. Two breakups, an unwanted pregnancy, and a tear-jerking death later, and Julie may just understand what it means to be alive.
Julie’s dissatisfaction with herself and uncertainty around what she wants influence her failed relationships in the film. This path toward understanding her heartaches leads to a profound ending that will leave audiences in tears.
7. Her (2013)
An award-winning movie by director Spike Jonze, Her centers on the emotional and thoughtful protagonist Theodore (Joaquin Phoenix), who writes personal letters for other people for a living. Still reeling from the end of his marriage, Theodore decides to pick up a new operating system, “Samantha” (Scarlett Johansson), and finds himself falling in love with the OS.
Yet another unconventional breakup movie, the 2013 masterpiece is a gripping and poignant tale that highlights the human need for connection. Her combines sci-fi and romance to create a truly unforgettable movie that will resonate with audiences who may feel especially alone after a harsh breakup.
8. Celeste & Jesse Forever (2012)
Celeste (Rashida Jones) and Jesse (Andy Samberg) are the typical high school sweethearts who married young in one of the best heartbreak movies ever, Celeste & Jesse Forever. Now, they second guess their relationship as greater differences between their priorities and goals make it impossible to align. When things spiral into a divorce, they both begin to doubt their decisions.
The rom-com uses humor and wit so well that audiences will never know what hit them when they start ugly crying.
For anyone who has had to let go of a long-term relationship, Celeste and Jesse’s struggles to accept moving on from the familiarity and comfort they gave each other will be too painful to watch.
9. Blue Valentine (2010)
Blue Valentine features career-best performances from Ryan Gosling and Michelle Williams, painting the image of a crackling marriage. Dean (Gosling) and Cindy (Williams) appear to be a normal couple to their modest neighborhood, but their lives are beginning to spiral as his lack of ambition challenges her efforts to further her nursing career. The film’s editing paces out their love story from its inception to their marriage and finally to its downfall.
Watching their relationship wilt created an emotional journey for the viewer as they felt what each character felt. The film’s capability to hit home with the honesty of broken relationships trying to survive created the opportunity for the ugliest of ugly cries when things didn’t turn out.
10. Brokeback Mountain (2005)
The epitome of the doomed love story, Brokeback Mountain fits perfectly in the ugly cry genre. Rodeo cowboy Jack (Jake Gyllenhaal) and ranch hand Ennis (Heath Ledger) stumble into a romance one night as they tend to a herd of sheep on Brokeback Mountain. The pair keep their on-off affair secret for decades after each marries their respective girlfriends.
In a story of hope and desire marred by expectations and fear, Gyllenhaal and Ledger provide top-notch performances as lovers that bring audiences to tears. Nothing is more emotionally provoking than a film where an audience is so desperate for the leads to be together that the consequences when it doesn’t come to fruition are devastating and cause the ever-popular ugly cry. Brokeback Mountain is an Oscar classic and an LGBTQ+ movie ahead of its time.