The 10 Saddest Books of All Time, Ranked

Image via Doubleday Published Sep 5, 2026, 6:51 PM EDT Jeremy has more than 2800 published articles on Collider to his name, and has been writing for the site since February 2022. He's an omnivore when it comes to his movie-watching diet, so will gladly watch and write about almost anything, from old Godzilla films to gangster flicks to samurai movies to classic musicals to the French New Wave to the MCU... well, maybe not the Disney+ shows. His favorite directors include Martin Scorsese, Sergio Leone, Akira Kurosawa, Quentin Tarantino, Werner Herzog, John Woo, Bob Fosse, Fritz Lang, Guillermo del Toro, and Yoji Yamada. He's also very proud of the fact that he's seen every single Nicolas Cage movie released before 2022, even though doing so often felt like a tremendous waste of time. He's plagued by the question of whether or not The Room is genuinely terrible or some kind of accidental masterpiece, and has been for more than 12 years (and a similar number of viewings). When he's not writing lists - and the occasional feature article - for Collider, he also likes to upload film reviews to his Letterboxd profile (username: Jeremy Urquhart) and Instagram account. He has achieved his 2025 goal of reading all 13,467 novels written by Stephen King, and plans to spend the next year or two getting through the author's 82,756 short stories and 105,433 novellas. Sign in to your Collider account Of all the books ever published, it’s inevitable that some are going to be sad. This shouldn’t be surprising to anyone, even those who might well admit that they don’t really read, and instead spend their time pursuing other forms of entertainment like movies, TV shows, or games. Books predate all those, and books likely influenced a bunch of those kinds of entertainment, even before taking into account how many adaptations of books there are out there. The challenge here comes not from observing the sadness of certain books, but from selecting a bunch of those sad books and highlighting them as the saddest. It’s a subjective thing, and that subjectivity is coupled with a rather overwhelming history of literature, and the unfortunate reality that one cannot (even if they live for a century or more), cannot read everything. So, here’s an honest attempt to rank some of the saddest books of all time, acknowledging that what one finds sad, another person might not consider so bad. 10 'Of Mice and Men' (1937) Image via Penguin Classics So, Of Mice and Men is one of those quintessential tearjerkers, probably being one of the first titles that comes to mind when you hear the term “sad book.” It’s a boring pick, then, when talking about sad books, but it earns its place here. It also earns that place here without being very long, since Of Mice and Men is a novella that doesn’t need the length of a novel to make you feel absolutely miserable. The narrative here concerns two men looking for work during the Great Depression, and continually experiencing that search becoming harder and harder. Of Mice and Men is nearly 90 years old, which has made some of it dated, but if younger readers are made aware of that in advance, there’s still a pretty good chance they’ll be made to read it in high school, and it’s one of the saddest books you might come across when still fairly young, as a result. 9 'A Storm of Swords' (2000) Image via Bantam Spectra The first installment of a series that feels worth mentioning, A Storm of Swords is the third book in A Song of Ice and Fire, which is an epic fantasy series that’ll hopefully be finished… one day… maybe. Anyway, for now, it’s the most emotional book of the bunch. There have been five novels planned, of seven, and if you want to know why this one’s especially emotional, but haven’t read the series, it’s the book that the show, Game of Thrones, adapted for its third and fourth seasons. Yes, A Storm of Swords was eventful enough to be the source material for two whole seasons, and so that one absolutely devastating episode in season 3… yeah, that part of the story is in A Storm of Swords. Honestly, that’s the main reason for including this book here. The other A Song of Ice and Fire books have their disturbing and downbeat moments, but that wedding of a red variety has them all beat, and makes this third book stand out as particularly depressing. 8 'Wuthering Heights' (1847) Image via Chartwell Some people might try telling you that Wuthering Heights is a romantic novel, but sometimes, some people are wrong. There are feelings of longing and desire here, but the passionate stuff is also destructive, and Wuthering Heights is more focused on looking at the lingering effects of trauma, alongside exploring prejudice, class, inequality, and all sorts of other things that aren’t particularly romantic. There are some adaptations of Emily Brontë’s source material that lean into romance, or have things play out as a love story of a bittersweet nature, but in the book, there is not much love, traditional or otherwise. In its place, you do get a ton of sadness in Wuthering Heights, and it’s remarkable how much of that emotional devastation still packs a punch close to two centuries on from the novel’s publication. 7 'Pet Sematary' (1983) Image via Hodder Paperbacks Because you're reading (or skimming through) something put together by a hopeless Stephen King fanatic, Pet Sematary is not going to be the only book by the author here. Apologies if that’s a problem. But if there’s one book by King worth singling out for its sadness, it’s Pet Sematary, because it’s quite in your face as a novel about death and grief, with the main characters living next to a cemetery, and because it’s a Stephen King book, that cemetery seems able to bring pets back to life. Pet Sematary itself will never be buried/forgotten about, and even if it were, people would gladly dig it up to revisit it, or at least do that so they can recommend it. The family cat dies and is resurrected. Chaos ensues, especially when the question of “Does this work with human beings as well as pets?” arises. Pet Sematary itself will never be buried/forgotten about, and even if it were, people would gladly dig it up to revisit it, or at least do that so they can recommend it. It’s a remarkable and uncompromising novel, and definitely one of King’s most raw and emotionally intense. 6 'Mason & Dixon' (1997) Image via Henry Holt and Company Mason & Dixon is fairly surprising with its emotion, because Thomas Pynchon is not a particularly sentimental author, to put it mildly. His books are generally engaged with intellectually more than emotionally, and to be fair, there is also quite a bit to think about and analyze when it comes to Mason & Dixon as well, though it’s got a bit more of an emotional kick than you might be expecting, alongside all the absurdity, confusion, and episodes that prove unusually funny. The main characters here (Charles Mason and Jeremiah Dixon) existed in real life, though Mason & Dixon does stray further from history than most historical fiction, owing to the exploits of the titular characters being presented as a story within a story. And Pynchon writes the whole thing unusually, even by his standards, mirroring/parodying the style of certain literature from the 1700s. It’s an interesting book, to say the least, and the ways that it proves touching and bittersweet really do prove startling (in a good way, not to mention a hard-to-explain way). 5 'The Subtle Knife' (1997) Image via Scholastic UK Within the His Dark Materials trilogy, Northern Lights might be the best book, but The Subtle Knife is probably the most emotionally impactful. Northern Lights you have to start with, either way, and then The Subtle Knife is the middle chapter of the trilogy. The Amber Spyglass wraps things up, and has some events that are probably supposed to be about as tearjerking as The Subtle Knife, but it just doesn’t quite get there. The third book is messy, to say the least. Lots of it works, and even when it’s not working, its ambition can be admired. Worst-case scenario, it’s an instance of “two out of three ain’t bad.” As for The Subtle Knife specifically… well, highlighting the saddest scene here would be a huge spoiler, but you'll know it when you come to it. It’s perfect, and also so emotionally brutal. 4 'Harry Potter and the Deathly Hallows' (2007) Image via Bloomsbury There was a point at which the Harry Potter movies were not able to match the intensity found in the books, and that point was crossed well and truly before the seventh and final book in the series (and its two-part film adaptation): Harry Potter and the Deathly Hallows. To focus on the books, though, they do ratchet up in intensity gradually and quite logically, with the characters dealing with more challenging things the older they get. So, if you yourself were growing up while these books and/or movies were coming out, and you weren’t too young when they first started coming out, you could probably handle each new one. If things got a bit too sad with book #7, that’s understandable, since Harry Potter and the Deathly Hallows doesn’t really mess around. It’s got “Death” (or “Deathly,” technically) in the title, and you do get a lot of death here, alongside other things that really drive home a sense of finality. It’s great, but definitely bittersweet stuff, as far as closing chapters go. 3 'The Dark Tower VII: The Dark Tower' (2004) The Dark Tower VII: The Dark Tower concluded the mainline The Dark Tower series, as the seventh and final main book, though The Wind Through the Keyhole came later (but proved to be an inessential interquel). This book is the grand finale, and without giving away what happens here, or most of what happens in the preceding six books, it is indeed focused on the final stage of Roland’s journey to that infamous Dark Tower. If you read this book in isolation, it would be confusing and make it hard to see what all the hype was about. When you read it after the first six books, though, the final part of The Dark Tower packs so many emotional wallops in a row. It’s even more brutal on an emotional front than the finale that was Harry Potter and the Deathly Hallows, with the sadness here (your mileage may vary on how bitter or how sweet this bittersweet book ultimately is) feeling undeniable. 2 'Les Misérables' (1862) Image via Penguin Classics While it was originally written in French, rather than English, Les Misérables doesn’t really lose anything in translation by maintaining the French title for readers outside France. It’s a book about lots of unfortunate people living during a tumultuous and emotionally strained time in history, with that history being stuck to, even if the people who either experience or observe the real-life events here are actually fictional. That’s historical fiction for you, in a nutshell. An honorable mention should probably go out to War and Peace, which does some comparable things to Les Misérables and is itself fairly moving at times, but Les Misérables is more outwardly tragic. It’s also safe to say that it paved the way for plenty of sad and/or tearjerking stories to come (for better or worse), so it scores high here, for present purposes, thanks to its historical value within the overall world of literature. 1 'A Little Life' (2015) Image via Doubleday If you're talking about books that have a certain notoriety for being sad, and you don’t give a mention to A Little Life, people are going to start seriously raising some eyebrows. So, here’s A Little Life. It’s a long book, and it’s distressing for that lengthy amount of time, with the narrative here focusing on a group of friends who all have some extreme personal demons they're dealing with. Much of that stuff’s from the past, so you get a sense of why those things were horrible and sad in that history, and then there’s a further exploration of how all those downbeat events continue to impact everyone in the present. There’s something to be said for this book’s braveness, and its willingness to tackle so many difficult things thematically, but you'd also be forgiven for sticking to admiring A Little Life from afar, rather than getting caught up in all its sadness, if it’s just not the kind of thing you need in your life right now. A Little Life Release Date September 28, 2023 Runtime 219 minutes Director Ivo van Hove Writers Koen Tachelet Cast James Norton Jude St. Francis Luke Thompson Willem Ragnarsson Omari Douglas Jean-Baptiste "JB" Marion Zach Wyatt Malcolm Irvine