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The Diary of a Young Girl by Anne Frank1984 by George OrwellThe Road by Cormac McCarthyA Story of Yesterday by Sergio CoboNight by Elie Wiesel
Most Depressing Book of All Time
1,229 books — 3,948 voters
Thirteen Reasons Why by Jay AsherSpeak by Laurie Halse AndersonThe Lovely Bones by Alice SeboldIf I Stay by Gayle FormanBefore I Fall by Lauren Oliver
Best Depressing Books
429 books — 429 voters

Where the Red Fern Grows by Wilson RawlsOld Yeller by Fred GipsonMarley and Me by John GroganThe Art of Racing in the Rain by Garth SteinThe Curious Incident of the Dog in the Night-Time by Mark Haddon
The dog dies...a cautionary list.
369 books — 273 voters
Forbidden by Tabitha SuzumaWe Were Liars by E. LockhartThe Lovely Bones by Alice SeboldThirteen Reasons Why by Jay AsherThe Bell Jar by Sylvia Plath
Books that punch life and happiness in the gut, and make the reader want to go to the nearest bridge over water and jump (but they don't, because that would be horrible)
231 books — 165 voters

Wuthering Heights by Emily BrontëThe Handmaid’s Tale by Margaret AtwoodAnna Karenina by Leo TolstoyTess of the D’Urbervilles by Thomas HardyThe Road by Cormac McCarthy
Masters Of Misery
408 books — 101 voters
The Hunger Games by Suzanne CollinsThe Meat Market by James ChalkDivergent by Veronica Roth1984 by George OrwellUglies by Scott Westerfeld
Wow, What a Crappy Future
62 books — 55 voters

American Psycho by Bret Easton EllisFahrenheit 451 by Ray BradburyA Clockwork Orange by Anthony BurgessOne Flew Over the Cuckoo’s Nest by Ken KeseyNot Okay by Brett Axel
Dark Literary Fiction
138 books — 55 voters
The Giving Tree by Shel SilversteinLove You Forever by Robert MunschCoraline by Neil GaimanDer Struwwelpeter by Heinrich HoffmannSylvester and the Magic Pebble by William Steig
Nightmare Fuel for Children
129 books — 43 voters

The Fault in Our Stars by John GreenLooking for Alaska by John GreenIf I Stay by Gayle FormanBridge to Terabithia by Katherine PatersonThe Book Thief by Markus Zusak
Depressing Books
45 books — 23 voters
Watch Us Dance by Leïla SlimaniWuthering Heights by Emily BrontëThe Poisonwood Bible by Barbara KingsolverAnna Karenina by Leo TolstoyThe Virgin Suicides by Jeffrey Eugenides
Unhappy Families In Literature And Drama
37 books — 22 voters

Opal by Jennifer L. ArmentroutAnxiety by Danny WinterOnyx by Jennifer L. ArmentroutShiver by Maggie StiefvaterLiliana by Neva Squires-Rodriguez
Heart-Wrenching, Sob-And-Bang-Your-Head-Worthy YA Books
30 books — 14 voters
Hamlet by William ShakespeareRomeo and Juliet by William ShakespeareOf Mice and Men by John Steinbeck1984 by George OrwellOthello by William Shakespeare
Most Tragic Endings in Literature
41 books — 14 voters

Rabbit, Run by John UpdikeThirteen Reasons Why by Jay AsherThe Seven Husbands of Evelyn Hugo by Taylor Jenkins ReidThe Fountains of Silence by Ruta SepetysGhost Story by Peter Straub
Abandoned in 2020
91 books — 13 voters
And Then There Were None by Agatha ChristieBy Grand Central Station I Sat Down and Wept by Elizabeth SmartAll My Friends Are Dead by Avery MonsenMaus I by Art SpiegelmanWe Wish to Inform You That Tomorrow We Will Be Killed With Ou... by Philip Gourevitch
The Most Depressing Book Titles
35 books — 10 voters

Crime and Punishment by Fyodor DostoevskyMigrations by Charlotte McConaghyA Little Life by Hanya YanagiharaThe Big Sky by A.B. Guthrie Jr.I Am the Cheese by Robert Cormier
More books that are too sad and depressing!
34 books — 10 voters
Positivity Warrior by Jim SoreboVigil by George SaundersThe Gate by Natsume SōsekiHouse of Splendid Isolation by Edna O'BrienHomesickness by Colin Barrett
Amazon Customers Also Bought or Read: Death, Grief and Loss Edition III
103 books — 7 voters

The Handmaid's Tale by Margaret AtwoodEnder's Game by Orson Scott CardFrankenstein by Mary Wollstonecraft Shelley1984 by George OrwellThe Metamorphosis by Franz Kafka
Unhappy Endings: Speculative Fiction With A Tragic Ending Part I
102 books — 5 voters
Positivity Warrior by Jim SoreboDeath and the Gardener by Georgi GospodinovNever Say Never, Never Say Always by Susan S. WarnerLearn to Live Forward by Chidi IwuchukwuThe Old Man by the Sea by Domenico Starnone
Amazon Customers Also Bought or Read: Death, Grief and Loss Edition I
103 books — 5 voters

Positivity Warrior by Jim SoreboI'm Sorry I Cremated You by Jaclyn Michelle SmithNever Say Never, Never Say Always by Susan S. WarnerLearn to Live Forward by Chidi IwuchukwuThe Leaving Room by Amber McBride
Amazon Customers Also Bought or Read: Death, Grief and Loss Edition II
103 books — 5 voters
Positivity Warrior by Jim SoreboThe White Book by Han KangNever Say Never, Never Say Always by Susan S. WarnerLearn to Live Forward by Chidi IwuchukwuAs It Is in Heaven by Niall Williams
Amazon Customers Also Bought or Read: Death, Grief and Loss Edition IV
103 books — 5 voters

Positivity Warrior by Jim SoreboTravels with My Aunt by Graham GreeneNever Say Never, Never Say Always by Susan S. WarnerLearn to Live Forward by Chidi IwuchukwuCatholics by Brian Moore
Amazon Customers Also Bought or Read: Death, Grief and Loss Edition V
103 books — 5 voters
Positivity Warrior by Jim SoreboMust I Go by Yiyun LiNever Say Never, Never Say Always by Susan S. WarnerLearn to Live Forward by Chidi IwuchukwuThe Immortalists by Chloe Benjamin
Amazon Customers Also Bought or Read: Death, Grief and Loss Edition VI
71 books — 5 voters

The Picture of Dorian Gray by Oscar WildeOliver Twist by Charles DickensDombey and Son by Charles DickensThe Dawn of Evil by L.E. ParkerStone Forged by Peter J. Merrigan
Best Deaths of Villains in Literature
18 books — 4 voters
Adult Children of Emotionally Immature Parents by Lindsay C. GibsonBreaking the Chain by Stacie WebbGirl, Interrupted by Susanna KaysenThe Body Keeps the Score by Bessel van der Kolk
Depressing and boring non-fiction
4 books — 3 voters

The Man Without Qualities by Robert MusilThe Book of Disquiet by Fernando PessoaHamlet by William ShakespeareFranz Kafka by Franz KafkaAgainst Nature by Joris-Karl Huysmans
Doomer Side
75 books — 3 voters
The Road by Cormac McCarthyThe Foxhunter by Dr Andrew J RynneNever Say Never, Never Say Always by Susan S. WarnerAnimal Farm by George OrwellParable of the Sower by Octavia E. Butler
Almost Happy Endings: Speculative Fiction With A Bittersweet Ending
80 books — 3 voters

Grendel by John GardnerThe Foxhunter by Dr Andrew J RynneThe Last Syllable by Valeriano DiviacchiThe Martian Chronicles by Ray BradburyThe Book of Sorrows by Walter Wangerin Jr.
Unhappy Endings: Speculative Fiction With A Tragic Ending Part II
36 books — 3 voters
Pride of Baghdad by Brian K. VaughanSaikano by Shin TakahashiThe Foxhunter by Dr Andrew J RynneFrom Hell by Alan MooreCerebus, Vol. 16 by Dave Sim
Unhappy Endings: Comics With A Tragic Ending
51 books — 3 voters

Norwegian Wood by Haruki MurakamiDoctor Zhivago by Boris PasternakStoner by John WilliamsOne Hundred Years of Solitude by Gabriel García MárquezThe Corrections by Jonathan Franzen
Crying Over Spilled Milk
6 books — 2 voters
Winterkill by C.J. BoxSuicide Forest by Jeremy Bates
Unexplained Death
2 books — 2 voters

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