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15 sad movies on Amazon Prime guaranteed to make you cry

Grab some popcorn... and some tissues.

Jul 8, 2020, 8:32 pm*


Chris Osterndorf 

Chris Osterndorf

You’ve had a hard day at work, you recently got dumped, or the news of the day is just getting you down. What do you do for self-care? For starters, you open a bottle of wine, turn on one of these sad movies on Amazon Prime, and have yourself a good cry. Because movies might not fix your problems, but watching characters on-screen who are even more miserable than you is always a good temporary solution. Here are the saddest movies on Amazon Prime.

Sad movies on Amazon Prime

1) It’s a Wonderful Life

It’s seen its share of parodies, but Frank Capra’s 1946 film remains a bittersweet classic. It has some of the same narrative elements of A Christmas Carol, as an angel tries to stop George Bailey (Jimmy Stewart) from taking his life by showing him all the good he’s done. But it’s also a movie about family, second chances, and goodwill. —Audra Schroeder

2) Of Human Bondage

This adaptation of the W. Somerset Maugham novel is significant for one reason: Bette Davis’s performance. Davis knew the character of ferocious English waitress Mildred Rogers could be her breakout role and reportedly begged studio chief Jack Warner to let her out of her contract to play the part. When he finally acquiesced and Davis got the acclaim she knew she was destined for, Warner began a spite campaign to prevent her from winning the Oscar. She ultimately lost to Claudette Colbert for It Happened One Night (another role Davis herself had wanted), but she became the first and last person in Academy history to receive a write-in nomination, pulling off a coup so big that the rules were changed after 1934 to prevent such a thing from ever happening again. Davis would go on to win the Oscar the next year for her role in Dangerous, and again in ‘38 for Jezebel, in addition to receiving eight more nominations over the course of four decades. But it was Of Human Bondage that kicked off her career as one of Hollywood’s most talented and legendary actors.

3) Last Flag Flying

Richard Linklater finally has his road trip movie. Set in December 2003, Last Flag Flying opens with Steve Carell’s soft-spoken Larry “Doc” Shepherd tracking down his old friend Sal Nealon, played with foul-mouthed vigor by Bryan Cranston. The two were in Vietnam together, and Larry enlists him to help transport the body of his son, who was killed in Iraq. They pick up fellow vet Richard Mueller (Laurence Fishburne), who is now a man of God. And with that collection of personalities, the film sets off on an emotional journey that paints early aughts patriotism in dreary strokes. While his past films often focus on youth and romance, Last Flag Flying is more somber: 9/11 is still fresh; America’s less than a year into the Iraq War; we see footage of Saddam Hussein being captured and George W. Bush on TV. But the film is also a portrait of damaged men in middle age, which doesn’t always make for the most entertaining content. —Audra Schroeder

4) Sophie’s Choice

You could probably look up “sad movies” in an encyclopedia and find a picture Sophie’s Choice. The Oscar-winning Meryl Streep film, based on the novel by William Styron, has become a kind of cultural touchstone, evoked whenever someone has to make a hard decision (i.e. “that’s a real ‘Sophie’s Choice’”). Whether most people who use the phrase have actually seen the film is debatable, but for those who haven’t, let’s just say it’s about a woman struggling to overcome the trauma she suffered in a Nazi concentration camp and leave it at that.  

5) Wonder

Get your hanky ready, because Wonder will do a number on your emotions. Based on the popular book, Wonder is about Auggie (Jacob Tremblay), a young boy with a medical condition that causes a facial deformity. After years of homeschooling, Auggie’s parents (Julia Roberts and Owen Wilson) send him off to school for fifth grade, where not everyone is so quick to accept Auggie as he is. The movie is a treatise on kindness, and is the kind of movie that will resonate with kids and adults alike. Wonder is an uplifting movie that wants to put good into the world.

6) Precious

Precious is the kind of movie so achingly sad, so completely devastating, you may be leveled for a whole day after watching it. The title character, played by Gabourey Sidibe, is an abused, illiterate, HIV-positive teenager who’s pregnant with her second child in this 2009 Sundance and Academy Award-winner from Jeff Daniels. Based on the novel Push by Sapphire (which was also at one point the movie’s clumsy subtitle,) Precious’s journey is not an easy one to watch, but by the end of the film you will weep not only out of sadness but out of joy, as she finds some peace in learning to love herself and finding others who love her too. The performances are increcible across the board, earning Sidibe a Best Actress nomination for her work in the lead role and Mo’Nique a Supporting Actress statue for her work as Precious’s monstrous mother, Mary. Screenwriter Geoffrey Fletcher also made history when he became the first African American writer to take home an Oscar for Best Adapted Screenplay.

7) Arrival

The twist at the end of Arrival packs such an emotional gut-punch, it makes the movie hard to re-watch knowing what’s coming. But the film, about a linguist played by Amy Adams trying to communicate with a mysterious group of aliens who have landed on Earth, is so good you may want to revisit it anyway. Adams is sublime in a difficult role, and director Denis Villeneuve (Prisoners, Sicario, Blade Runner 2049) proves again that he approaches genre in a more interesting way than nearly every filmmaker working today.  

8) Fences

Have you seen Viola Davis cry? You have, right? Then you already know she cries like no one else. And she’s such a great actor, when she cries, you tend to cry too. Hence the power of Fences, Denzel Washington’s adaptation of the August Wilson play about a working-class Black family in Pittsburgh and their patriarch who’s constantly trying to rise able his circumstances. Washington plays Troy Maxson, the flawed husband and father at the center of the story, and Davis plays Rose, his caring but oft-neglected wife. The film isn’t particularly cinematic; you can tell it was originally a play. But the performances are complex, nuanced, and powerful. Washington was nominated for an Oscar for his role, and Davis won a much-overdue best-supporting actress trophy for hers.  

9) A Ghost Story

Rooney Mara and Casey Affleck play a couple whose happy life is upended when the husband dies. He returns in ghost form, a sheet with black eyes, to stay in the house for eternity while his wife moves on. Writer-director David Lowery has constructed a movie about time, space, and grief that’s intimate in its setting and expansive in its ideas. A Ghost Story is a distinct vision anchored by bold creative choices. —Eddie Strait

10) Jerry Maguire

Jerry Maguire has a lot of memorable lines. “Show me the money.” “Help me help you.” “Did you know that the human head weighs eight pounds?” But I submit to you now that none of the dialog hits quite as hard as “You had me at ‘hello.’” Cuba Gooding Jr. may have won the Oscar, but Jerry Maguire is nothing without the relationship between Cruise’s Maguire and Renée Zellweger’s Dorothy Boyd. Rarely has Cruise had such great romantic chemistry with a co-star, and if this confession of love doesn’t at least kind of melt your heart, you might be made of stone. Yes, director Cameron Crowe is at his most gloriously sentimental here. Don’t fight it. If it’s been awhile, make some time to say “hello” to Jerry Maguire again.

11) The Florida Project

The Florida Project is one of the best movies of 2017 and not enough people know about it. Writer-director Sean Baker follows up his iPhone-filmed Tangerine with this traditionally shot movie set at a Florida motel. It follows 6-year-old Moonee and her mother Halley, played by newcomers Brooklyn Prince and Bria Vinaite, respectively. The movie is told primarily from Moonee’s perspective, meaning there are many scenes of carefree kids finding fun wherever they can. Moonee and Halley both wreak havoc in their own ways, and their put-upon building manager Bobby (Willem Dafoe) often looks out for both of them, in addition to his other long-term tenants. The movie balances the joy of childhood and the ever-encroaching realities of adulthood in a way that is so true to life it can be hard to watch at times. The Florida Project challenges you to find sympathy for people you may normally look down on. It’s one of the best movies on Amazon Prime, and also one of the saddest.  —E.S.

12) On Golden Pond

Henry Fonda and Katharine Hepburn both took home Oscars for their work in this 1981 drama. A curmudgeon and his wife end up forming a surprising bond with the son of their daughter’s  (Jane Fonda) boyfriend. On Golden Pond is an earnest movie, with somewhat simple ambitions. But if you remember old Hollywood fondly, it’s impossible not to fall for Fonda and Hepburn’s performances. Watching these two titans, now in their twilight years, come together onscreen for one last bow is a natural conduit for the waterworks.

13) Manchester by the Sea

Manchester by the Sea is a tough watch, what with it revolving around a handyman, Lee (Casey Affleck, who won an Oscar for his performance), dealing with his brother’s (Kyle Chandler) death. Lee has to take in his nephew, Patrick (Academy Award-nominated Lucas Hedges) and grapple with his past failings. Despite the gloomy setting and gloomier subject matter, Manchester has a wicked funny bone. Writer-director Kenneth Lonergan specializes in crafting sincere characters and dialogue so authentic you’ll want to start a GoFundMe to help Lee and Lucas stay afloat while they figure things out.  E.S.

14) The Big Sick

The real-life relationship between Kumail Nanjiani and Emily Gordon provides the basis for this charming romantic comedy. An Amazon original movie, The Big Sick deals with the dynamic of the couple’s interracial relationship and how it affects their families, his family more than hers as well as Gordon’s hospital stay and medically induced coma. Nanjiani and Gordon wrote the script, with Nanjiani playing himself and Zoe Kazan playing Gordon. The movie is an honest, hilarious reminder that our differences are the best things about us. The Big Sick is one of 2017’s best films. E.S.

15) Moonlight

Barry Jenkins’ Best Picture-winning film tells the story of Chiron in three parts as he grows up and comes to terms with his sexuality and learning to be comfortable in his own skin. Chiron may be black and gay, and the movie’s focus may be narrow, but its themes are universal. There are moments so empathetic that I’m welling up a little just thinking about it. The cast is remarkable, from the three actors who play Chiron to Naomie Harris, Janelle Monae, and Oscar winner Mahershala Ali. Its status as one of the lowest grossing Best Picture winners means a ton of people need to catch up with it. —E.S.

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*First Published: Jun 21, 2018, 5:00 am