13. The Great Gatsby (2013)
Literature scholars may disagree on whetherThe Great Gatsbyis F. Scott Fitzgerald’s best work, but no one can deny it’s his most well-known.
Baz Luhrmann directed the fourth movie adaptation of the 1925 novel (sadly, the first of them is lost forever) and infused the historical with the contemporary, similar to what he did withRomeo + Julietin 1996.
Leonardo DiCaprio stars inThe Great Gatsby(as he also did inRomeo + Juliet), and of course he plays the titular billionaire Jay Gatsby, who’s like a Jazz Age Jordan Belfort with more heart and less swearing.
Opposite Jay Gatsby’s mansion is the small cottage of Nick Carraway, played in this version by Tobey Maguire. Nick is one of the few people allowed to meet the famously mysterious Gatsby, who built his empire for Nick’s second cousin Daisy (played by Carey Mulligan).
As it turns out, an empire isn’t enough for some people, and Gatsby ultimately lands with a bullet in his brain, punished for the fatal hit-and-run that Daisy was actually responsible for.
Related:The Best Movies About Rich People
12. A Star Is Born (2018)
A Star Is Bornhas had a fair number of remakes, with each version distilling the essence of its era. Those versions have starred Kathleen Crowley and Conrad Nagel; Judy Garland and James Mason; Barbra Streisand and Kris Kristofferson.
But the most recent iteration? This one not only stars Lady Gaga and Bradley Cooper, but it’s also Cooper’s directorial debut. He shines as director, but Lady Gaga steals the show after ditching her eccentric trademark style for this stripped-back drama role.
Bradley Cooper plays country rock singer Jack, who discovers drag bar waitress Ally when she sings on shift. Their love flourishes as Ally launches to fame, but Jack’s crippling alcoholism gets in the way and causes him to make permanently damaging choices.
Related:The Best Movies About Singers
11. Brokeback Mountain (2005)
Brokeback Mountainis pretty sad long before we get to the end of it, but it’s a subtle kind of sadness that’s made to mimic the emotional suppression that we see in the two main characters.
Rural Wyoming in the early 1960s wasn’t the most inclusive place for LGBTQ+ people, so cowboys Ennis Del Mar (played by Heath Ledger) and Jack Twist (played by Jake Gyllenhaal) must keep their secret homosexual affair under wraps.
The men-of-few-words spend their days isolated together on mountainous farmland, and although their passionate romance shocks them at first, they end up giving into their love for each other—until they return home, where they both play straight and start their own families.
When their marriages start to crumble, the two secretly meet up again for fishing trips. But Jack’s wife eventually delivers the news that Jack was killed in a car tire explosion, and director Ang Lee suggests Ennis knows otherwise (with violent images of Jack getting beaten to death).
Grief has never been so quietly yet powerfully portrayed as when Ennis sobs into an old shirt that Jack used to wear on the mountains.
Related:The Most Emotionally Devastating Movies
10. Stand By Me (1986)
The ending toStand By Meis heartbreaking narratively, thematically, and contextually. A triple hit for the old ticker.
Based on the novella by Stephen King,Stand By Mefollows four best friends on a hike through the Oregon wilderness as they look for a rumored dead body. Why? To become local heroes, of course.
Plot-wise,Stand By Meis from the POV of an older Gordie who’s looking back on the trip for his memoirs. Played as an adult by Richard Dreyfuss, Gordie tells us the gang lost touch in high school, with one serving jail time and the other getting stabbed in a restaurant.
The whole story is an examination of lost innocence, mourning death, and an end to the carefree days of childhood.
Related:The Best Friend Groups in Movies
9. The Boy in the Striped Pajamas (2008)
WhereasStand By Meis more abstractly sad,The Boy in the Striped Pajamasis a straight-up hard-hitting tragedy. But what else would you expect from a Holocaust movie?
Mark Herman directs this adaptation of John Boyne’s harrowing novel, and although some critics thought it was a little exploitative, I’d make a bet that you can’t watch it without crying!
Children are about the closest thing to purity. Before they’re taught to hate or judge, they’re blind to prejudice and able to see everyone as equal playmates. It’s from this angle thatThe Boy in the Striped Pajamasunfolds, taken from the POV of eight-year-old Bruno (played by Asa Butterfield) whose Nazi family has just moved to Poland.
Not understanding that his SS father is a bad man, Bruno plays in the fields and stumbles upon an extermination camp. There, he befriends a Jewish boy called Shmuel (played by Jack Scanlon), believing the camp to be an ordinary farm.
When Shmuel’s father goes missing, Bruno sneaks in to help find him. Both boys are ushered into a communal shower, hands clasped, but it’s not water that comes pouring down…
Related:The Saddest Movies of All Time
8. Logan (2017)
Logandoesn’t justlooklike a Western. If you want to understand all the references in this fantastic film, I recommend watchingShanefirst. You know, the 1950s Western classic by George Stevens.
That’s the same movie young Laura (impeccably played by Dafne Keen) watches and eventually recites from at her father’s grave.
Set in a barren 2029 Texas, Logan/Wolverine (played by Hugh Jackman) is too old to keep up with his powers, while the great Charles Xavier (played by Patrick Stewart) has lost his telepathy to dementia.
Mutants have been destroyed and enslaved, but Logan leaves retirement to save his estranged daughter and other mutant kids that have been experimented on. (Even the plot runs parallel toShane.)
Loganstands out in theX-Menfranchise because of its indie-feeling drama, R rating, and lack of levity that’s usually found in superhero films.
Related:The Best Movies About Father-Daughter Relationships
7. Shutter Island (2010)
The final line of Martin Scorsese’sShutter Islandstings so much because it reveals that Andrew Laeddis (played by Leonardo DiCaprio) ischoosingto end his life, even if he pretends to forget.
Forget what? Well, rewind back to the beginning where Andrew is introduced to us as Teddy, a US Marshal who’s investigating a missing persons case on Shutter Island.
Located on Boston Harbor, this island is home to the criminally insane, which means you really don’t want people going missing here! Meanwhile, Teddy is accompanied by his partner Chuck (played by Mark Ruffalo), who’s actually Andrew’s shrink in real life.
His so-called investigation is a game created to help Andrew process the death of his three kids, who were murdered by his wife. Andrew then killed his wife and, understandably, lost his marbles.
The tragedy ofShutter Islandis that this is Andrew’s last chance to accept his real identity before being lobotomized, and so the question stands: Is it not better to die a good man?
Related:The Best Movies About Mental Asylums
6. Life Is Beautiful (1997)
Like Bruno and Shmuel inThe Boy in the Striped Pajamas, little Giosuè (played by Giorgio Cantarini) doesn’t understand what a concentration camp is despite being in one.
Why? Because his father pretends that the whole thing is a game being played to win a big prize. Giosuè is only four years old, so he really believes all the gags and schemes cooked up by his father.
In reality, Guido (played by Roberto Benigni) is a Jewish bookstore owner in Nazi-occupied Italy. He and his family are seized by the Germans and thrown on a train bound for Auschwitz—and upon arrival, Guido and Giosuè are separated from their wife/mother.
Life Is Beautifulis simultaneously the most upbeat and most depressing Holocaust movie around, as Guido uses humor to distract his son. Eventually Giosuè is freed from Auschwitz and reunited with his mother, oblivious to the fact that his father has already been shot…
Related:The Best WWII Movies of All Time
5. La La Land (2016)
The ending toLa La Landisn’t just cleverly executed, but also permeated with a melancholic nostalgia for what could have been, the everlasting"what if" that taunts most human beings in some way.
For Mia (played by Emma Stone) and Sebastian (played by Ryan Gosling), it’s not a “what if I chased my dreams and made it” scenario… because they’ve both already done that. After all, Mia is a famous actress and Seb owns his own jazz bar.
For them, it’s a “what if we chose each other instead?” scenario because the whole story is about picking between romance and career.
This conclusion makesLa La Landuniquely happy and sad at the same time, a double-edged sword that will divide audiences on what they think the couple should have done.
All of this is amplified by Damien Chazelle tricking us with a false ending, where old home movies play out their idyllic family life. Then, the two meet again at Seb’s jazz bar in real time, only to share the glance and the memory of this “what if.”
Related:The Best Romance Drama Movies
4. Dead Poets Society (1989)
If you were told in advance that one of the characters inDead Poets Societywould commit suicide, you’d probably guess it was Todd (played by Ethan Hawke). He’s awkward, shy, bullied, and pressured by his parents who put him in a strict all-male prep school in 1950s Vermont.
Todd comes out of his shell thanks to the unorthodox methods of his English teacher John Keating (played by Robin Williams), who inspires some of the boys to continue the forbidden “Dead Poets Society,” which Keating was a member of during his student days.
But it’s Neil Perry (played by Robert Sean Leonard) who shocks us. He’s extroverted, smart, likable, funny, passionate… yet his acting pursuits and suggested homosexuality are demonized by his father, who signs Neil up for military school. Except, he never makes it.
Related:The Most Inspirational Movies That Celebrate Life and Joy
3. The Green Mile (1999)
You’ll want to avert your gaze inThe Green Milemore than once. Just so you know what you’re in for, you can expect: a sabotaged death-by-electric chair with a dry sponge; the child rape and murders of Wild Bill; the taking of an innocent man’s life, and more.
Paul Edgecomb (played by Tom Hanks) recalls all of this from his days of working on death row in the 1930s. He’s accustomed to all kinds of cruelties, but never has he faced a genuinely kind soul awaiting the death penalty—nor has he ever encountered magical healing powers.
Stephen King’s original novel is fantastic for its blend of grounded drama and supernatural forces, but it’s really the performance of Michael Clarke Duncan as John Coffey that has us weeping here.
Despite his towering build, John Coffey is accused of murder out of racism rather than justice, and he takes away the pain of others by giving it to himself. The fact he begs for the electric chair as mercy says it all…
Related:The Best Movies About Prison
2. Requiem for a Dream (2000)
Director Darren Aronofsky looks at addiction from two very different ends inRequiem for a Dream, a title that references the characters' dreams that are lost to an existence of living dead. The whole thing plays out like a tragic, paranoid fever dream set to a haunting musical score.
Firstly, there’s Harry and Marion (played by Jared Leto and Jennifer Connelly), a twenty-something couple who yearns to leave the ghetto but can’t stop chasing that next hit of heroin.
Then, there’s Harry’s naïve mother Sara (played by Ellen Burstyn), who’s lonely, bored, and desperate to lose weight. She inadvertently gets hooked on diet pills, which are actually amphetamines that send her into a malnourished, psychotic state.
Both mother and son end up in the hospital for their respective addictions, with Harry losing an arm to needle infection and Sara ending up catatonic from electroshock therapy.
Related:The Most Psychedelic Drug Movies
1. Atonement (2007)
Atonementuses the same kind of red herring finale asLa La Land, but this one is much, much sadder.
Adapted by Joe Wright from the novel by Ian McEwan,Atonementis a war drama that begins in the pastoral English countryside, where oldest sister Cecilia Tallis (played by Keira Knightley) starts a secret affair with the housekeeper’s son Robbie (played by James McAvoy).
It’s a cataclysmic night when Cecilia’s cousin is raped on their estate, and her younger sister Briony (played by Saoirse Ronan) blames Robbie without evidence. Robbie is shipped off to prison before WWI breaks out, then he’s first in line to fight in the Battle of France.
Joe Wright’s agonizing long take of Robbie wandering the beaches of Dunkirk, dazed into a near hallucinogenic state, is concluded with the fact that Robbie and Cecilia eventually end up together.
But don’t sigh with relief just yet… because that ending is fabricated by Briony on account of her guilt. Both of them actually died during the war, and Robbie was innocent the whole time.
Related:The Best Movies About Forgiveness
