The 10 Best Bittersweet Movies For When You Need A Good Cry

The most bittersweet movies have the propensity to be some of the best because they combine that core feeling of mixed sadness and happiness that everyone has felt in their lives and is one of the defining elements of being human. Bittersweet movies are not necessarily the saddest movies ever, which would be films like Grave of the Fireflies or The Pianist where the tragic story is almost too incomprehensible to fathom and lingers after the film ends. Bittersweet movies tap into something more relatable or something with a message of hope at the end.

Conversely, there are bittersweet movies that can’t necessarily be referred to as “tearjerkers”. The story and ending may elicit a hopeful laugh rather than a tearful smile. Remember the Titans, 500 Days of Summer, and Edward Scissorhands all have bittersweet elements to their stories, but aside from a scene or two, aren’t focused on making viewers cry. The best bittersweet movies are heartrending but have a message of hope or happiness that’s inextricable from the rest of the story.

10
Eternal Sunshine Of The Spotless Mind

Released In 2004

Eternal Sunshine of the Spotless Mind is a science fiction romance from cerebral filmmaker Charlie Kaufman. In the movie, Joel Barrish (Jim Carrey) discovers that his longtime ex-girlfriend Clementine Kruczynski (Kate Winslett) has undergone a new procedure to wipe away any memories she’s had with him. He decides to do the same and, in the process, realizes that just because some of the memories were bad, doesn’t mean he wants them all gone. As the memories fade, the last one of Clementine urges Joel to, “Meet me in Montauk.”

Then his memories are gone. Two years of a relationship have been stripped away, and it’s heartbreaking watching Joel realize he’s made a mistake, both in the breakup and in erasing the evidence. The worst parts of his relationship are shown in excruciating detail, but it’s his commitment to finding the woman he loves that is the sweetness of the film. Even after they realize their relationship didn’t work out the first time, they decide to try again anyway. It’s uncertain, unclear, and hopeful.

9
La La Land

Released In 2016

Some relationships dissolve because of one particularly brutal moment, and others fall apart because it’s the best choice for everyone involved, and it’s those breaks that can be the saddest. La La Land, starring Ryan Gosling as Seb, a musician, and Emma Stone as Mia, an actor, follows the young couple as they fall in love in the city of stars and slowly realize throughout the film that they have to break up. They both fell in love with one another because of their passion for music and acting, respectively.

As it turns out, the best way for them to pursue those passions is for the pair to go their separate ways. It slowly dawns on Seb and Mia that they will never be who they want to be, and who the other wants them to be, together. There is no massive fight; it’s just the bittersweet recognition that while they love one another, they can’t be together. The final sequence of the film as they imagine what their lives would have been like together is poignant, but their secret smile at one another suggests contentment with their choice.

8
Toy Story 3

Released In 2010

There may be another Toy Story after Toy Story 3, but the third film in the Pixar franchise is the end of an era. The first Toy Story came out in 1995 and children who grew up with it were around college age when Toy Story 3 arrived, making for a particularly affecting end to Andy’s story as he became a stand-in for the viewers. In the third movie, Andy is preparing to leave for college and decides to donate Woody, Buzz, and the rest of the toys to a daycare.

They end up instead in the possession of Bonnie, a young girl, and a suitable replacement for the loving Andy. The sequence in which Andy and Bonnie play with the toys just as Andy did at the beginning of the original Toy Story, set to a score by Randy Newman, is a nostalgic look back at the character’s childhood and many of the viewers’. It’s a bittersweet lesson Andy learns at the end of Toy Story and one many do as they grow up. He has to move on from his childhood, but that doesn’t mean everything he loves disappears.

7
Casablanca

Released In 1942

Casablanca is often ranked among one of the greatest movies ever made — for good reason. Set during World War II, the romantic drama follows American expatriate and nightclub owner Rick Blaine (Humphrey Bogart) who gives up on his stubborn neutrality to help his former flame Ilsa Lund (Ingrid Bergman) get her new husband Victor (Paul Henreid) out of Vichy, France. From the moment Sam (Dooley Wilson) plays “As Time Goes By” to the finale with one of the saddest goodbyes in movies, Casablanca is a bittersweet ode to courage and love.

The unconsummated romance between Rick and Ilsa is one for movie history and Rick’s selflessness in imploring her to leave with her husband is what bittersweet movies are made of. What makes these courageous and self-sacrificial moments so affecting is that the film was made during the war and real feelings of loneliness and loss affect the story. In a famous sequence, French refugees begin singing their national anthem “La Marseillaise” to drown out a group of German singers. Some of those singers were French refugees (via The Globe and Mail).

6
Brokeback Mountain

Released In 2005

In Ang Lee’s most celebrated movie, Brokeback Mountain, two Wyoming cowboys, Ennis Del Mar (Heath Ledger) and Jack Twist (Jake Gyllenhaal), find love and companionship during a summer spent herding sheep. The sensibilities of the 1960s West keep the pair apart and though they both start families, neither can give the other up. It’s a painful and all too real look at how small-minded thinking and fear damage the innocent love of Jack and Ennis and the people they bring into their lives to hide their true selves.

Ennis is so unable to access how he feels that his mouth barely opens when he talks; the words only slip out, even when he’s alone with Jack. Neither man can find acceptance, and even self-acceptance is hard to uncover. Brokeback Mountain is a devastating look at love and regret. Still, the bittersweet end of the movie, with Jack’s mother silently acknowledging Ennis’ love for her son, and Ennis’ daughter inviting him to her wedding, suggests that perhaps men like Jack and Ennis won’t have to hide forever.

5
Once

Released In 2007

A tearjerking romantic musical, Once follows a Dublin busker known only as “Guy” (Glen Hansard) who meets “Girl” (Markéta Irglová), a Czech immigrant whose husband will be coming to the country later in the year. Guy and Girl form a friendship around their considerable musical talent and the Once soundtrack is as eye-watering as most movies. Though it’s clear both Guy and Girl have a connection, neither of them acts on it, as she is married.

The ballad they make together, “Falling Slowly”, perfectly expresses the sentimental and bittersweet feelings the movie is filled with. The joy of finding a like-minded friend, the butterflies that come with slowly falling in love, the regret that prudence can produce, and the powerful feelings that come with doing the hard thing are all wrapped up in Once.

4
Lion

Released In 2016

Based on a true story, Lion is a powerful, tragic, and ultimately triumphant story about a man’s search for his family. The film depicts the life of Saroo (Dev Patel), who in 1986 gets separated from his brother and lost in Calcutta, India. Saroo is eventually put in an orphanage and an Australian couple adopts him. Years later, Saroo begins researching where he came from to try and find his biological mother and his increasing desperation pushes away his girlfriend and his family.

However, the pain, fear, and discontentment he’s felt in his life are rewarded with Saroo’s discovery of his hometown. Saroo arrives, shell-shocked to see places from his memory take shape. Then he sees his mother, greatly aged, but still alive. Their reunion is one of the most heart-wrenching and exultant moments in recent movies. Saroo was gone, but now he’s home. Lion ends with the tragic reminder that “MORE THAN 80,000 children go missing in India every year,” and while that’s a sobering fact, it’s also an important acknowledgment to celebrate Saroo’s determination and his mother’s faith.

3
If Beale Street Could Talk

Released In 2018

Based on the novel by James Baldwin, If Beale Street Could Talk depicts 1970s Harlem, where a young couple named Tish (KiKi Layne) and Fonny (Stephan James) are expecting their first child together. When Fonny is wrongfully accused of rape, Tish and her family fight the system to free him. It’s a relentless look at the way Black people were treated in the era and a stark reminder that, for many, their treatment has improved little. Despite their best efforts, Tish is unable to convince the court of Fonny’s innocence.

Depressing and disheartening, If Beale Street Could Talk finds love and humanity in Tish’s drive to help her powerless husband. She never wavers and though he does eventually have to plea to get his sentence down, Tish visits him at the end of the film with their new daughter. It’s a bittersweet symbol of how the justice system, with all its power, can’t discourage Tish from standing by the man she loves.

2
Terms of Endearment

Released In 1983

Terms of Endearment is a James L. Brooks family comedy-drama that stars Shirley MacLaine and Debra Winger as Aurora Greenway and her mother, Emma Greenway-Horton, respectively. Emma and Aurora have a complex relationship that is incredibly close but also very contentious. Over 30 years of their lives, the mother and daughter fight with one another, begin relationships and families, and ultimately find their way back to each other.

Those with complicated relationships with their parents will recognize the all too real shared feelings of adoration and frustration that can come from dealing with an overbearing guardian or an obstinate child. The humor and heartbreak on display from the four Oscar nominees and two winners at the center of the cast create an undeniably tear-jerking film that ends with a scene of understanding and devotion that people only find after decades spent together.

1
Dead Poets Society

Released In 1989

Robin Williams as English teacher John Keating in Dead Poets Society is every talented and memorable high school teacher who has ever inspired an unmotivated child. Taking place at the Welton Academy, an all-male boarding school in Vermont, a class of promising but overmanaged students learn from Mr. Keaton, the power of poetry and “seizing the day”. The film has now been parodied ad nauseam, but watching scenes like Keaton encouraging Todd (Ethan Hawke) to read a poem in front of his class is still spine-tingling.

Of course, the realities of upper-crust society set in, and Keaton is removed from the school, but not before inspiring his class to stand up to their fathers, teachers, and each other. When the boys stand up on their desks and hail, “O Captain! My Captain!” to the departing Mr. Keaton, it’s one of the most bittersweet movie moments of all. Keaton is gone, but the boys remind him, the administration, and their fellow students what it really means to live a life inspired.