Ten Books That Make You Cry

Our sweetest songs are those that tell of saddest thought

Our sweetest songs are those that tell of saddest thought.
- Percy Bysshe Shelley, from “To a Skylark”

There’s something about sad music and sad stories that draws us. This is not necessarily because we are morbid, or because we’re mawkish, or because we want simply to luxuriate in the griefs of others. Rather, I think, it’s because empathizing with the griefs of others can bring home to us that we are not alone in our own. Many writers have dealt with the theme of grief, in all its various aspects. Some depictions have, indeed, that quality of sweetness that Shelley spoke of; others depict grief as bitter, angry, destructive. Here are ten notable instances of authors addressing this universal theme.


Wordsworth and Coleridge published the first edition of Lyrical ballads in 1798, and it was a revolution: turning their back on high-flown vocabulary and complex forms, they used very simple rhythms and simple diction, and focussed on everyday events in ordinary lives. This poem, written in very simple language, describes almost casually, as if in passing, the grief a father bears for his dead daughter.

This short poem is written, as many of Wordsworth’s poems are, in the form of a popular ballad, with simple, repeated rhythms and everyday words. You wouldn’t guess from the first two verses that this is a poem about grief. A hunt is ready to depart, and there is a sense of festive bustle. Whatever we may feel about hunting these days, it was a popular activity back then, and Wordsworth conveys the sense of a joyful, colourful day – at least for the hunters, if not the hunted. It is only in the third verse that we get a sense of grief underlying the jollity and the festivity: Timothy’s child, his “last”, had died “not six months before”. (We are not told whether the word “last” implies merely that she was Timothy’s youngest child, or that she was his last surviving child: the title of the poem suggests the latter.)

Wordsworth does not enter into Timothy’s mind. He tells us in the fourth verse that Timothy shut the door in a “leisurely fashion”, and goes on to speculate in the fifth and final verse why he did so. “Perhaps”, the poet thinks, when he took the key, he remembered the person who used not so long ago to open the door from him, and who is now no longer there. Wordsworth gives us just one more detail: Timothy has a tear on his cheek. In the midst of all the celebrations, all the jollity, Timothy bears the weight of his personal grief, and of remembrance. Wordsworth leaves it to the reader to determine what Timothy’s loss means to him.

To quote from another (and more famous) poem by Wordsworth,

But she is in her grave, and oh,
The difference to me!


2) "The Age of Innocence" by Edith Wharton

We all love a sad love story. This one is set amongst the cream of American society in the 1870s. Here, decorum and correctness are all-important: society has its rules, and not to conform to them is … well, it’s bad form. It’s not the done thing. But what happens when real human emotion enters into all of this? Well, it just has to be sacrificed, because that’s how things are. Sad love stories don’t really come much sadder than this.

The novel opens at the opera. All of society is there, present and correct. Correctness is what is most important. No matter what happens, no matter what you feel inside, your behaviour outside has to be correct. It is what society demands. Outward form is everything.

It is in such a society that Newland Archer, engaged to a young lady with an impeccable family background, finds himself falling in love with his fiancée’s cousin, the Countess Ellen Olenska. She has been unhappily married to a Polish nobleman, and is now separated from him. And, to the horror of her family, she is considering divorce. This is not the done thing. Whatever inward agonies one may experience, one must, on the outside, be correct.

Newland Archer marries his fiancée, intending, certainly, to do the right thing. But his love for his wife’s cousin develops into a passion, and this is something that the correctness of social etiquette does not allow for.

The Age of Innocence is among the saddest of love stories. To live with other people, to live within a society – any society – we must take into account society’s rules. But we have little control over what we feel, and our feelings accept no rules. What then?

The title is ironic. But then again, possibly not. This novel, though set in the 1870s, was published in 1920, on the other side of the Great War, and during the rise of what we now call “modernism”. In both style and content, this is a very old-fashioned novel, and must have appeared so even at the time. Maybe, for all its faults, the age depicted was, after all, an age of innocence! Even when passions suppressed led to sad and unfulfilled lives.


3) “Long Day’s Journey Into Night” by Eugene O’Neill

This was such a personal play, that O’Neill did not publish it or allow it to be performed in his lifetime. It shows us four members of the Tyrone family (a fictionalised version of O’Neill’s parents, his elder brother, and himself). Over the course of a single day, they struggle with the past, and try to come to some sort of understanding of the events of their past that have shaped the tragedy of their present. This play depicts like no other the sadness of lives gone wrong.

This very long play takes place over one single day, with the final scene taking us deep into the night – a night that is both literal and metaphorical. The four members of the Tyrone family – father, mother, two sons – keep thinking about the events of the past. And they keep talking about it, endlessly. They have to do this: they have to come to some sort of understanding of how these events of the past have shaped their present. They seem to love and hate each other at the same time. They blame each other for all that has gone wrong in their lives, but none of them can walk away: they are too intimately attached to each other.

The cumulative effect of it all is tremendous. Some productions cut the text, but if the cuts go too far, it doesn’t work: we need to feel the cumulative effect of these characters obsessing about the past, repeatedly, simply because they can’t help themselves.

The play is raw and painful, but there is also an underlying tenderness that binds these four people together. It ends with the mother recalling when she had first met and had fallen in love with James Tyrone: “Yes, I remember. I fell in love with James Tyrone and was so happy for a time.” Those last three words are pure heartbreak: I cannot think of any line, anywhere, sadder than this.

For many, this play is too harrowing and too depressing. But paradoxically, in certain works of art, depression can be a path towards something that defies description, but which is, in a strange way, also uplifting.


There’s a great sadness in becoming old. Shakespeare here reflects on his relationship with his young mistress. She does not admit that she is unfaithful to him, and he, in turn, does not admit that he is too old for her. They both deny what they both know to be true. As Shakespeare muses wistfully on their self-deceptions, he finds himself bemused by all this absurdity, but is also aware of the tremendous sadness of it all.

“Lord! What fools these mortals be!” says the fairy Puck in A Midsummer Night’s Dream. Shakespeare seems to be thinking much the same in this sonnet. Time passes, we become old, and, if we weren’t such foolish mortals, we’d accept that. The problem is, we are foolish mortals, and we indulge in all sorts of self-deceptions to avoid admitting what we all know to be true – that we are becoming old, and that, with age, our powers fail.

Shakespeare starts this sonnet talking not about his age, but about his mistress’ unfaithfulness. She says she isn’t unfaithful to him, and he pretends to believe her. And his reason for pretending is subtle: he wants her to think of him as someone young and inexperienced, and naïve in these matters. But he knows that’s not true. And he knows that she knows that’s not true. But he goes on pretending anyway – just as she goes on pretending she is faithful to him. They both know what the truth is, and both pretend they don’t.

“Therefore I lie with her and she with me,” Shakespeare muses. They sleep with each other, they lie to each other, they lie even to themselves – anything rather than face the inevitable sadness of their lives. We lie to ourselves even when we know what the truth is, even when we don’t believe our own lies.

Lord, what fools we mortals be!


5) “The English Teacher” by R. K. Narayan

Narayan’s fictional world is essentially a comic world, but even in comedy, tragedy can strike. The principal character here is happy in his marriage. Perhaps the hardest thing a writer can do is to communicate happiness, but Narayan succeeds. But then, death comes, almost out of nowhere. Narayan does not dwell on the grief, but when another man appears claiming to be in touch with his dead wife’s spirit, things take an unexpected turn. The final pages are incandescent.

Narayan’s writing seems effortlessly elegant and charming. I say “seems”: it must take an awful lot of effort to appear so effortless. But he really couldn’t write a clumsy sentence if he tried. The fictional world he presents is, overall, comic, and is utterly delightful. But he does not shirk the darker aspects of life, and when tragedy strikes, the effect can be devastating.

In this novel, the protagonist, Krishna, is a happily married young man. Not rich, by any means: far from it. But happy in his marriage. Communicating simple happiness is a tremendously difficult thing to bring off, and Narayan succeeds superbly. But then, seemingly out of nowhere, death appears. No reason: it’s just one of those random, senseless things that nonetheless change our lives. And Krishna is left with the devastation.

Into this scene of desolation, a stranger appears, claiming to be in touch with the spirit of Krishna’s dead wife. What follows is a journey towards enlightenment, and ends with perhaps the most miraculous and joyous passage I think I have encountered in fiction.

We often speak of “tragicomedies”, where the tragic and the comic are given equal prominence. I don’t think it has ever been done better, and with so unobtrusively light a touch.


6) “Elektra” by Sophocles

Elektra mourns for her murdered father, and her exiled brother, and desires revenge on those who have caused her so much grief. A brief summary of the plot would indicate that Elektra triumphs by the end. But we cannot help asking herself: what has been the price paid for this triumph? What has such excess of grief, and the hatred that has resulted from it, done to her soul? There are no easy answers in this most troubling of plays.

The first audiences of these plays, in Ancient Athens, would have known this story well. Elektra’s father, Agamemnon, has been murdered by Clytemnestra, his wife. Having murdered her husband, she had sent their son Orestes into exile. And she now lives with her lover Aegisthus. Her daughter, Elektra, mourns for her dead father, and awaits the return of her brother Orestes, so they could, together, exact revenge for their dead father. And this is precisely what happens: by the end, Elektra triumphs. Sophocles does not change this story.

And yet, Sophocles leaves us deeply uneasy. What has such unremitting grief done to Elektra’s soul? Sophocles does not ask this question directly: he allows us to see for herself how deformed and twisted Elektra has become.

The play is horrific. Elektra remembers well the terrible murder of her father. The very palace walls seem to be dripping blood. And at the end, Clytemnestra is killed by her own son. (He goes on to kill his mother’s lover also.) In Greek tragedy, acts of violence always take place offstage: the audience does not see the killings. But what the audience does see is, perhaps, even more horrific. As her mother is being struck down, as her screams of terror resound across the theatre, Elektra too is screaming – but hers is a scream of joy: “Strike again – strike harder!”

“Too long a sacrifice can make a stone of the heart,” wrote Yeats. This is what grief can do to people, and it is not ennobling.



Here, we have the sadness of wasted lives. It is hard to tell how exactly this happens. When we are young, we are full of high ideals, of energy; but then, slowly, imperceptibly, we become old, and not just physically: our ideals disappear, our sensibilities become coarsened, and only rarely, if at all, do we catch even a glimpse of the extent of our decline. This short story, a mere twenty or so pages, seems to capture all the sadness of our unfulfilled lives.

In films and novels and plays, we are generally presented with dramatic events that change the course of the characters’ lives. But in real life, individual events are rarely so dramatic: what changes the course of our lives are not usually dramatic moments, but, rather, the accumulation over the years of small things – sometimes so small that we don’t even notice them. But then, in middle age, if we ever look back, we find we are not what we once had been. And neither are we what we had hoped to have been. Somehow, slowly, imperceptibly, we have changed, and all our idealism, our optimism, our youthful dreams, have disappeared.

The central character in this story is Dmitry Ionych Startsev, who comes to a small provincial town as a doctor. He visits a local family, and falls in love with Yekaterina, but she has dreams of her own: she wants to go to Moscow, away from all this provincial dullness, and become a concert pianist. But nothing works out as hoped for, for either of them. Slowly, imperceptibly, Doctor Startsev – “Ionych”, as everyone contemptuously call him – loses whatever youthful vitality he once had; he becomes fat, and he looks forward now only to counting his earnings at the end of each week. How did all this happen? There’s no real answer to that question: it just did. Whatever flame he had in him became extinguished.

No-one has captured the sadness of wasted lives as well as Chekhov.


8) “Great Expectations” by Charles Dickens

This famous novel is about a great many things, but at the centre of it, it seems to me, is the pain of unrequited love. For all that Pip does, all the mistakes of his actions and errors of his judgements, are in pursuit of that which is beyond his reach. Pip goes on to redeem himself morally, but the pain of unfulfilled longing remains.

Everything he does, he does for Estella. He wants to become a gentleman because he thinks this will help him win Estella. He even rejects his old friend, the honest and gentle-hearted Joe, because he feels Estella would disapprove of such low company. She becomes his obsession.

Later in the novel, Pip befriends Estella’s father, and, as he is dying, tries to comfort him. The daughter he has had and thought he had lost, Pip tells him, is still alive. She has found powerful friends. She is wealthy. She is beautiful. And he, Pip, loves her. But there is one thing Pip cannot tell him, because he can barely tell this even to himself: he cannot tell her father she has grown up an emotional cripple, unable to return the love he offers her.

Many refer to the ending as a “happy ending”. Well, read for yourself and judge: I shall not reveal it for those who have not read it yet, and who are in the fortunate situation of being able to read this wonderful work for the first time. But speaking for myself, I do not think any ending can be happy: there cannot be any happy ending to this saddest of all novels. Pip may have learnt something of the true moral values of our lives, but the wound in his heart remains unhealed.

This novel breaks my heart every time I return to it.


Gerard Manley Hopkins possibly suffered from what we, in modern parlance, would call “clinical depression”. In this sonnet, he describes his despair, and his incomprehension in the face of the fact that the religion he still so fervently believes in can offer him no comfort. “The mind has mountains,” he says, and these extraordinary lines give us an unforgettable picture of the mind’s mountainous terrain.

“No worst, there is none.” The opening line recalls perhaps the most terrible tragic work of them all – Shakespeare’s King Lear. “The worst is not till we can say this is the worst,” says Edgar. No matter how bad everything is, it could get worse still. Hopkins was a very religious man, but even for him, the Comforter provides no comfort, and Mary, “mother of us”, provides no relief. He is utterly lost.

“O the mind, mind has mountains.” It is an unforgettable image. Our human mind is something that is utterly mysterious, “no-man-fathomed”. And it is a dangerous landscape, with “cliffs of fall frightful, sheer”. There is only one comfort – and that is, this torment will not last for ever: “All life Death does end”.

The sonnet had started with a reference to Shakespeare, and it ends with another: “Each day dies with sleep”. The reference here is to The Tempest: “Our little life is rounded with a sleep”. In Shakespeare, that “sleep” is obviously a euphemism for death, but Hopkins applies that seeming euphemism not to “our little life”, but to every day (“each day dies with sleep”). The terror of death is depicted as an everyday thing. And yet, it is the only comfort we have.

Hopkins very likely suffered from depression, and these few lines convey the horror of that condition with a quite startling immediacy.


Ma Parker, an elderly lady who earns her meagre pennies from cleaning rooms of people wealthier than herself, has had a hard life, filled with tragedy. But the latest blow, the death of her beloved grandchild, breaks her. And perhaps the worst of it is that she is utterly alone in her grief. Whatever sympathy is offered is lightly felt, or is insincere. And she does not even have anywhere where she could sit down and cry, where she could give vent to her inconsolable grief.

Katherine Mansfield’s stories, like Chekhov’s, seem to capture the entire essence of a human life within just a few pages. In this story, we have a character who is referred to as a “literary gentleman” – a young man, bachelor, who is, presumably, a writer. He is indeed the kind of person we’d expect a literary short story to be about. But Mansfield’s focus of interest is the charlady, who comes to clean for him, and who is, generally, beneath anyone’s notice. The “literary gentleman”, who, presumably, writes about people, barely notices her at all. On hearing that her grandson had died, he expresses what he thinks is a kindly thought: he even congratulates himself on doing so. He has no idea of the sheer intensity of her grief. Nor, indeed, does he have any interest in finding out.

There are a number of narrative shifts in this story. We move soon to Ma Parker’s own thoughts. She has had a difficult life, full of tragedy. All this she has borne in patience, but this latest tragedy has broken her utterly. And the worst is that she has no-one to share it with. Any sympathy expressed is but superficial, as the literary gentleman’s has been. By the end, there is literally nowhere she can go to – nowhere where she could cry over her latest loss, over, indeed, her entire grief-stricken life.

In this story, we are on our own. What grief we have is ours alone: the world has no time for it, and, like the literary gentleman, merely passes by.
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