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The 30 Saddest Endings in Literature

When the end comes, there will be tears.

The 30 Saddest Endings in Literature
28 August 2023

We all love it when a story ends happily. The couple end up together, the good guys win, the evil forces have been well and truly put in their place. But how realistic are they?

The greatest works of literature are packed with some memorable happy endings, but it's far more common, realistic and beautifully tragic to explore the sad ones. The ones that leave you feeling like your heart has been ripped out of your chest or like the colour has been sapped from the world.

Because even though they might be painful to read in the moment, some of the saddest literary endings are also hands-down some of the best.

With that in mind, here are more than 30 of the saddest endings to befall some of the greatest works of literature. Get the Kleenex out; you might be needing them.

Oh, and it should go without saying, that what you are about to read includes a momentous amount of spoilers. Don’t say you weren’t warned…

See our list of Best Dystopian Novels

1984 - George Orwell

Far from defeating Big Brother, the tragic figure of Winston Smith succumbs to the menace of the all-seeing totalitarian state. He rejects Julia and most crushingly of all he loves Big Brother. A horrid foretaste of the crippling inertia that society can bring to bear on all.

The 30 Saddest Endings in Literature

Flowers by Algernon - Daniel Keyes

This devastating book is told through a series of first-hand reports, which detail an experimental treatment to increase the intelligence of a man called Charlie. The operation is a success and Charlie's intelligence more than triples, but the effects don't last long and his newfound smarts begin to regress. The fact it's written as if Charlie himself is entering reports or diary entries makes it all the more gut-wrenching as he learns more about the world then must come to terms with less.

The 30 Saddest Endings in Literature

A Monster Calls - Patrick Ness

Although this is sometimes marketed as YA or a children's book, adults will enjoy it too. And when we say enjoy, we mean feel deeply moved and devastated by the end. A Monster Calls follows the story of Conor, who finds out his mum is terminally ill and begins to have strange dreams. One night he's visited by a mysterious presence, a monster, who tells him stories. To add to the sadness of the ending of this book, the woman who originally came up with the story idea, Siobhan Dowd, was terminally ill with cancer at the time and died before she could write it.

Of Mice And Men - John Steinbeck

George Milton and Lennie Small are one of literature’s most celebrated and yet most unfortunate double acts. Two drifters in search of work, their tale is emblematic of many migrant workers during the Great Depression. And even though you know their journey is doomed, the end (George killing Lennie in an act of unparalleled mercy and friendship) is no less heart breaking.

Doctor Faustus - Christopher Marlowe

Man sells his soul to the devil. Man is doomed. The end.

The Metamorphosis – Franc Kafka

In a work of warped and fantastical imagination, Franz Kafka has the protagonist of The Metamorphosis, Gregor Samsa, mutate into a bug. Gregor turns into a lonely and miserable recluse. He sees out his days hidden in a bedroom until a wretched death spares him, and his family, any more suffering.

One Day - David Nicholls

Dexter and Emma spend the best part of 20 years somehow managing not to get together – when it’s plain to the dear reader that the pair belong to each other. Which of course makes Emma’s messy demise, hit by a car, after they finally do embark upon a romantic relationship all the more torturous.

American Psycho - Bret Easton Ellis

Patrick Bateman reckons himself a man of substance; a man of strong character that gets things done. His murderous rampage is surely evidence of his immoral fortitude. Yet, come the novel’s end we are asked to see Bateman’s acts as nothing more than some dark, but ultimately redundant, wish fulfilment. Bateman is as blank as the corporate culture at which he worships.

In The Country of Last Things - Paul Auster

Dystopian novels rarely have happy endings and Paul Auster’s mesmeric In The Country of Last Things is no exception. Anna Blume’s story is no picnic – death, attempted rape, miscarriage, murder all discolour her life in this most heartless of post-apocalyptic societies – but just as you hope her life might show some form of redemption, you’re left with utter hopelessness. The sadness at the heart of this epistolary novel is sealed when you realise the letter Anna sends to her friend recalling her experiences is unlikely to have been read.

Tess of the D'Urbervilles - Thomas Hardy

In a Mills & Boon novel Tess and Angel would not have been doomed. The romantic misfortunes of their youth would be transformed by the hope of maturity. Thomas Hardy didn’t see it that way though. There was to be no salvation for poor Tess. The novel ends with a black flag being raised over the prison after her execution.

The Age Of Innocence - Edith Wharton

Love is something of an illusory and cryptic emotion until it arrives. Before Newland Archer meets Countess Ellen Olenska he is secure in the belief that his marriage to May Welland will be a happy one. His love – real love – for Ellen, May’s cousin, has to be denied, however, as he is forced to do the honourable thing. The book ends 26 years later, May has died but once again Newland chooses to deny himself.

One Flew Over The Cuckoo's Nest - Ken Kesey

Randle Patrick McMurphy is one of the most ebullient characters in literature – a rebellious thorn in the side of authority. He provides his fellow inmates at a psychiatric hospital with glimpses of freedom. However, after one too many confrontations with Nurse Ratched, McMurphy’s zest for life is extinguished after he’s given a lobotomy. His friend, Chief, puts him out of his misery by suffocating him, but McMurphy’s earlier metaphorical death is almost too sad to bear.

The Great Gatsby - F Scott Fitzgerald

Daisy runs over Myrtle killing her; Wilson, Myrtle’s husband, thinks Gatsby is to blame so he shoots Gatsby before turning the gun on himself. Daisy and Tom run off into the night, their future bound to be one of privilege but unhappiness. Nick is fed up with everything he has witnessed. The jazz age distilled into an emotional wreck.

Villette - Charlotte Bronte

Lucy Snowe finally finds happiness with the schoolmaster M. Paul Emanuel, but on his return journey from the West Indies, Lucy hints that his ship is destroyed in a terrible storm. A cruel blow for a woman who suffers throughout Bronte’s book.

Never Let me Go - Kazuo Ishiguro

The doomed triptych of Kathy, Ruth and Tommy are unlikely to find the ending they want. All three are revealed to be clones devised so that they can provide vital organs for ‘normals’. Ruth dies after making a completion but not before urging Kathy and Tommy to become involved romantically. As the pair begin to uncover their past, however, resignation to their fate seems the only destiny. Upon Tommy’s ‘completion’ (death), Kathy begins her final journey.

Young Goodman Brown - Nathaniel Hawthorne

"And when he had lived long, and was borne to his grave... they carved no hopeful verse upon his tombstone, for his dying hour was gloom." So ends Nathaniel Hawthorne’s short story. Following events in the town of Salem (the story is set during the town’s infamous witch trials) the protagonist, the titular Goodman Brown has lost his faith, the love for his wife and proceeds in a gloomy, disaffected fashion until his disillusioned end.

The Idiot - Dostoyevsky

Prince Lev Nikolayevich Myshkin is a kindly, positive soul whose cheerful demeanour is at odds with the corrupt modernity of St Petersburg. The women who fall for his charms both meet unfortunate ends – his rival Rogozhin kills Nastassya and Aglaya marries a fraudulent Count – and he is forced to return to hospital.

Hamlet - Shakespeare

Shakespeare penned numerous tragedies, but none so dramatic, so pertinent, and so enduring as the bloody tale of the Prince of Denmark. Revenge, sadness, deceit, betrayal permeate the story at every turn. Hamlet avenges his father’s death at the hand of his uncle, but also dies.

The End of the Affair - Graham Greene

The title of Graham Greene’s masterpiece hints at happiness being torn asunder, but the misery that unfolds within the pages is sadness writ large. Maurice Bendrix and Sarah Miles relationship – the affair in question – comes to a sudden and untimely end, but the emotions live on. Sarah eventually dies from a lung infection.

We Need To Talk About Kevin - Lionel Shriver

We know that Eva Plaskett’s son Kevin is an evil, murderous sociopath. This we can glean from the letters she writes to her presumably estranged husband Franklin. However, as the novel reaches its denouement we learn that Franklin does not live on. Kevin murdered him and his sister before he embarked on his bloodletting at his school. Chilling.

Revolutionary Road - Richard Yates

Yates’s compelling dissection of suburban ennui and human loneliness reaches a shocking crescendo after the Wheelers – Frank and wife April –embark on a mutually exclusive journey of self-destruction. After learning she is expecting their third child – something Frank doesn’t want – she attempts to self-abort, bleeding to death in the process. Frank is haunted by this turn of events. As he probably should be.

Gone With The Wind - Margaret Mitchell

Rhett and Scarlett’s love affair was always a tempestuous one, but after the death of their beloved daughter Bonnie, happiness becomes increasingly hard to locate in the Butler household. Rhett does one, delivering his classic parting shot: ‘Frankly, my dear, I don’t give a damn.” Harsh. But fair.

Brave New World - Aldous Huxley

Dispirited by the vapidity he experiences in the Brave New World, John The Savage escapes society and seeks an ascetic life to cleanse himself. His methods – which include self-flagellation – unfortunately intrigue society and he is visited by numerous visitors. He hangs himself at the end of the book.

The Road - Cormac McCarthy

A father and son trudge across the unforgiving terrain of post-apocalyptic Earth. Their journey is dark, disturbing and highlights an almost beautiful bond between the pair. And then the father dies. And the son guards his corpse.

Great Expectations - Charles Dickens

The original ending to Dickens’ tour de force was considered too sad and so was revised. In it after all they have been through Pip and Estella meets on the streets after her abusive husband dies. She seems to have some sort of heart after her mistreatment by Miss Havisham. In the new ending the pair meet in the ruins of Miss Havisham’s ruined Satis House. Do the pair finally get together? Most prefer the first ending despite the overbearing forlorn theme.

Washington Square - Henry James

Catherine Sloper ends Henry James’ classic novel a middle-aged spinster. Her romantic rendezvous with Morris Townsend eventually comes to nothing. The final sentence reads: “Catherine, picking up her morsel of fancy-work, had seated herself with it again - for life, as it were.” Pass the hankies; we got something in our eye.

On Chesil Beach - Ian McEwan

Two young people, Edward Mayhew and Florence Ponting, marry in the summer of 1962. They are both virgins. They take their honeymoon at Chesil Beach in Dorset. Both are petrified about their wedding night. It is, naturally, a disaster. The death of love, hope and optimism ensues.

For Whom The Bell Tolls - Hemingway

An American Robert Jordan fights against the fascists in the Spanish Civil War. He meets the love of his life, Maria, while fighting, but is betrayed at the novel’s critical juncture. Mortally wounded, Jordan tells Maria and his other comrades to escape while he faces death – and Franco’s fascists – alone.

The Boy In The Striped Pyjamas - John Boyne

While many found the plot objectionable, the story of Bruno, the son of a Commandant at Auschwitz and Shmuel, a Jewish child held captive there (wearing striped pyjamas), is an understandably emotional one. At the end, Bruno also puts on a pair of striped pyjamas and tries to help his friend find his father. All they find is the gas chamber. Not a dry in the house.

The Secret History - Donna Tartt

Come the end of Tartt’s excoriating expose of the morality (or lack thereof) of a group of classics students at a rich American college, it’s clear the misfits have literally got away with murder. But this comes at a price for the novel’s narrator, Richard Papen. He is drifting through life when he dreams of his former mentor Henry. Richard asks Henry if he is happy in death. His response is chilling: “Not particularly. But you’re not very happy where you are, either.”

The Dark Tower - Stephen King

It’s no surprise that Stephen King doesn’t trade in trite, sugar-coated happy endings, but even the most battle-hardened King devotees are feeling the pinch come the conclusion of The Dark Tower, the seventh book in the Dark Tower series. Eddie and Jake are dead, Oy, the dog of the anti-heroic Roland Deschain, is impaled on a tree branch, and Roland is left with no peace.

The Beastly Beatitudes of Balthazar B - J.P. Donleavy

There’s a haunting melancholy and infinite sadness to JP Donleavy’s majestic The Beastly Beatitudes of Balthazar B. Despair is never far away and at the conclusion, his best friend is financially ruined and the love of his life is dead. Apart from that, everything is tickety-boo.