25 Books That Define Cool

Let’s abandon the childish notion that reading isn’t cool. We’re grown men here and reading happens to be one of the many ways we enjoy spending a bit of our free time. Of course, sitting down with just any book doesn’t always make for a great experience. We want to read something with wit, masculinity, and a pervading sense of effortless cool. Here are 25 books that fit that description perfectly.

1. The Sun Also Rises (Ernest Hemingway)

This list could easily include just about everything Papa Hemingway wrote. His terse style and penchant for booze are common throughout his catalog. If we were to pick one, however, we’re going with The Sun Also Rises. His first novel includes bullfighting, fishing, and drinking, but is really about love, desire, and masculinity. (Link)

2. The Art of War (Sun Tzu)

Written over 2,500 years ago, The Art of War is still as important today as it was for warriors back then. The first real work on military strategy, The Art of War is a study in knowing yourself, knowing what you’re up against, and applying some brain to a clash of brawn. Today, its applications extend far beyond the battlefield as required reading for businessmen and modern intellectuals. (Link)

3. Fear and Loathing in Las Vegas (Hunter S. Thompson)

Honestly, you could put just about every book from the good doctor on this list – Hell’s Angels and The Rum Diary come to mind – but if you had to pick one, you have to go with Fear and Loathing in Las Vegas and all its drug-fueled insanity. If you’ve never read it, the opening sentence should give you a good idea of what you’re in for: “We were somewhere around Barstow on the edge of the desert when the drugs began to take hold.” Long live Gonzo journalism. (Link)

4. Slaughterhouse-Five (Kurt Vonnegut)

There have been many war books released in the last few years and many are very, very good, some even make a strong antiwar case without just putting the idea out there (see: Billy Lynn’s Long Halftime Walk), but none of these can do what Slaughterhouse-Five did. Vonnegut accomplished something so bizarrely amazing, he wrote a book that is light-hearted and easy to read yet incredibly poignant and dark. (Link)

5. Trainspotting (Irvine Welsh)

You’ve probably seen the movie, but have you read the book it was based on? It’s one of the rare cases where both are fantastic. Welsh’s writing will take a little getting used to, and you’ll probably be speaking with an accent inside your head, but once you get the hang of it, you’re off on a grittier ride than even the film could provide. (Link)

6. Walden (Henry David Thoreau)

With the outdoorsman renaissance happening as we speak, it is nice to look back at one of the books that probably started it. Walden isn’t the bore you read back in middle school, it takes time to appreciate like a nice bottle of red. Thoreau’s masterpiece tackles so much while quietly nudging your brain into activity. It also makes you want to build a cabin. (Link)

7. Blood Meridian (Cormac McCarthy)

Blood Meridian paints an image of brutality that no film could match. While McCarthy has plenty of worthy candidates for this list (see: The Road and No Country for Old Men), we still believe Blood Meridian to be his finest work. The story focuses on a group of bounty hunters and The Kid, a rebelious teen who joins the group, as they hunt down Indians. While that’s the story, the real focus of McCarthy’s work is violence and that little seed of evil in all of us. (Link)

8. Gravity’s Rainbow (Thomas Pynchon)

With the exception of The Sound and the Fury, there may be no other book that is so universally loved or hated as much as Gravity’s Rainbow. The book almost defies definition. It’s like a bizarre trip. Read it for the language and imagery, the overwhelming sense of paranoia and death, and if you don’t have any LSD lying around. (Link)

9. Rabbit, Run (John Updike)

The greatest mid-life crisis novel of all time doesn’t actually deal with a mid-life crisis at all. Harry “Rabbit” Angstrom is 26 when he decides to leave his wife and son for a new life. Of course, what that new life is, and what exactly he wants out of it isn’t clear to the reader or to Rabbit himself. It will strike a cord with all men who struggle with the idea of settling down. (Link)

10. Fight Club (Chuck Palahniuk)

Chuck Palahniuk didn’t calmly stroll onto the literary scene, he kicked the damn door down. Fight Club was his first and most widely-known work. Even if you’ve seen the movie, which you probably have, you’re doing yourself a disservice by not reading the book. One of the movies that define cool also happens to be one of the books that does as well. The novel is so original, so thought-provoking, and so maddeningly brilliant, it will make you want to get copies of Survivor, Choke, and Palahniuk’s other works. (Link)

11. All Quiet on the Western Front (Erich Maria Remarque)

If All Quiet on the Western Front didn’t have the ability to stop war from happening, no book will. The author drew from his experiences in WWI and put together one of the most well-known war books of all time. The story is of a fresh-faced German soldier encountering the trials and tribulations of training and the horrors of battle. The totality of the soldier’s experience is captured without the author turning a blind eye. (Link)

12. The Amazing Adventures of Kavalier & Clay (Michael Chabon)

The Amazing Adventures of Kavalier & Clay appeals to the child in all of us who wants nothing more than to be a real-life superhero. It’s cool, because, no matter how macho or seemingly tough, every guy has wanted to escape at some point. Oh, also because it is brilliant. (Link)

13. The Catcher in the Rye (J.D. Salinger)

Yes, it’s a cliche pick, but The Catcher in the Rye has to be on this list. Roll your eyes at it because you think you’re too cool and it’s too mainstream, but The Catcher in the Rye is the quintessential “cool” book. Teenage rebellion at its finest. (Link)

14. The Professional (W.C. Heinz)

Any book that can claim Hemingway as a fan, is worth checking out if you ask us. The Professional is about boxing, but it’s really about what separates pros from impostors and about caring for a craft. The story creeps along, and in that slow, meticulous pace is its brilliance and its power. (Link)

15. All the King’s Men (Robert Penn Warren)

An all-time classic filled with the muck of politics and of life. Loosely based on the story of Huey Long (former governor of Louisiana), All the King’s Men is not only written poetically, but it also happens to be gripping and difficult to put down. The story twists and turns while never losing steam. We suspect a copy is on Frank Underwood’s shelf. (Link)

16. Under the Volcano (Malcolm Lowry)

The backdrop: The Day of the Dead. The subject: An alcoholic on the brink of destruction. Under the Volcano is about the struggle every man faces against the beasts that ensnarl him. (Link)

17. Last Exit to Brooklyn (Hubert Selby)

The cool of Last Exit to Brooklyn lies in its rawness and realness. It lifts a veil that it refuses to drop. The book takes you inside the seedy underbelly of an American city and pulls you along for the ride even when you want to turn back. Welcome to urban hell. (Link)

18. American Psycho (Bret Easton Ellis)

Graphic violence and humor aren’t often a combination for success, but Bret Easton Ellis weaves the two perfectly. Patrick Bateman, a wealthy and good-looking New Yorker, spends his evenings plotting death and murdering associates. It engages themes like it was a slick, modern work of Dostoyevsky. (Link)

19. Bright Lights, Big City (Jay McInerney)

Few books capture the feel of New York like Bright Lights, Big City. It somehow delivers that vastness of being in the city when you’re young and struggling. Oh, and it has plenty of drugs. (Link)

20. Tropic of Cancer (Henry Miller)

It was porn before porn was porn. Any book that was banned for decades has a certain cool allure to it, and while Tropic of Cancer could have been obscene at the time, it is actually just shockingly honest. It was truly ahead of its time. (Link)

21. The Adventures of Huckleberry Finn (Mark Twain)

The first great American novel made young men want to pull out a pocket knife and find adventure outside of a television screen. Among the social issues it tackles, is a story about adventure and growing up. (Link)

22. Into Thin Air (Jon Krakauer)

If you’re familiar with Krakauer only through the movie adaption of Into the Wild, you really need to read this book. It’s a first-hand account of a deadly trek up Mount Everest. It’s a gripping narrative that showcases the sheer brutality of survival. Man versus mountain, though man doesn’t always win. (Link)

23. The Prince (Niccolo Machiavelli)

Because few things are as inherently cool as power. It’s the leadership book before there was a dearth of business writers filling the shelves at Barnes & Noble. If you want brutal honesty about what it takes to be a successful leader or a political powerhouse, The Prince still holds up today. (Link)

24. The Outsiders (S.E. Hinton)

The Outsiders is timeless. Replace greasers and socs with modern cliques and gangs and the feelings still ring true. The author was only 16 when she wrote it, so the emotions come off truer than those of someone looking back on their teenage angst. Just because it was required reading in middle school doesn’t mean it isn’t cool. (Link)

25. Tree of Codes (Jonathan Safran Foer)

There is something cool about doing your own thing, and with Tree of Codes, Jonathan Safran Foer has done just that. While Everything is Illuminated and Extremely Loud and Incredibly Close are both masterful works that have a sense of uniqueness to them, they don’t come close to what the author did in Tree of Codes. He takes his favorite book, The Street of Crocodiles by Bruno Schulz, and cuts out lines, words, and pages to create his own unique narrative with what is left behind. It’s both book and art. (Link)


  • Ana

    Whew. All my life since 8th grade I’ve thought I was the only one not impressed by Catcher in the Rye.

  • Ana

    You are hereby my favorite commenter, purely for “dearth”

  • James Donnelly

    Am I misunderstanding if I thought To Kill A Mockingbird was cool? That should have definitely been on the list, but as someone stated, there is a lack of female novelists featured here.

  • UmCaitlynx

    1. On the Road – Kerouac
    2. Naked Lunch – Burroughs
    3. Catch-22 – Heller
    4. Notes From the Underground – Dostoevsky
    5. Post Office – Bukowski
    6. The Great Shark Hunt – Thompson
    7. The Bell Jar – Plath
    8. To Kill a Mockingbird – Lee
    9. The Story of Junk – Yablonsky
    10 Angela’s Ashes – McCourt
    Just to start.

  • Ameya Benare

    though its a really nice book, god of all things, is far from cool.

  • Anamika Kapoor

    daughter of smoke and bone is quite cool but not in your list

  • dirtyhobo2k12


  • chris is a douchebag

    Now who’s the pretentious douche…. idiot.

  • Guest

    Have either of you connoisseurs read “The House of Mirth”?

  • Chris

    Have you read “The House of Mirth”?

  • Christoph Tietje

    In case you haven’t noticed yet. There are books on this very planet that could be labeled cool, but are not written by Americans.

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  • Young Angels Publication

    Children’s A To Z Encyclopedia Book

    A dictionary is a poetic knowledge about everything from head to toe. It is gaining the vocabulary and the terminology, knowing about things in all aspects. It is important for us to realize how potent words are. They can change the meaning of a sentence, and give a new thread to the golden meaning of life. we present you something exciting and adventurous. The series is your ‘romance’ with words from monuments to places to great persons and from vocabulary to group collections. The series has it all. You name it and we have it. Hope you enjoy through this whirlpool of words. Enjoy happy reading in this world of words.

  • InfiniteJest

    Dude, the name of the website is ‘cool material’. Has the idea that ‘cool’ in ‘cool’ books was picked as the adjective for that reason touched you?
    David Foster Wallace is missing, Primo Levi (If this is a man) is missing, Oscar freacking Wilde is missing. Some huge, big time, life changing literature is missing. It’s 25 books, it’s obviously missing a lot of great stuff. Just stop complaining.

  • http://www.cheese.com/ John Goatbirth

    Duuuuuuuuuuuuuuuuuude. What a Hipster.

  • InfiniteJest

    You know, for a self-titled fan of literature, your vocabulary seems to be pretty shallow.

  • http://www.cheese.com/ John Goatbirth

    I happen to agree with your first comment, but you started it with “dude”. It’s an excellent way to negate your argument.

  • InfiniteJest

    I was just conforming to lexical stereotypes of language which I’m not a born speaker of.

  • http://www.cheese.com/ John Goatbirth

    Good for you. As the great Kawabata once wrote, “Innit, blud!”.

  • thing#2

    Cat in the hat..bestest book ever!

  • http://dbakeca.com Dbakeca Italia

    great tips

  • Anon

    White cis men represent!

  • zonkedout1

    The Prince by Machiavelli was like 1984 today. Then, it was written to warn people that this is how power happens. It was a warning, not an instruction manual.

  • johnd

    “The sun also rises” easily one of the worst, if not THE worst book I ever almost read. Got about halfway. The conversation is inane the characters indolent and stupid, and the plot devoid of any interest or suspense. Do NOT waste your time. If you want to read Hemingway, “For Whom the Bell Tolls” is superb.

  • Sargon

    Albert Camus’ “The Stranger” notably missing from the list.

  • Chetoos

    Fight club was a great movie, but i cant say the same of the book.
    And I really love books and cinema.

  • Mary de Pleave

    What a miserable list of books! ‘Cool’- I don’t think so. War, violence, drugs. power and macho nonsense. Alright there may be good writing on these topics, but enough. Does there always have to be an enemy? It’s about time “peace” was cool. Let’s hear something positive- apart from the Salinger and Thoreau the titles make me wince. Whose society are they a reflection of I wonder!

  • tootthefirst

    Along with Shakespeare, Blake, Dostoyevsky, Proust, Arendt, Chaucer, the Greeks and any # of others. If that’s the list of what the cool kids read, color me nerd.

  • Charoy

    I don’t have a problem with “The Sun Also Rises.” It’s standard Hemingway fare and ol’ Ernest is nothing if not macho. But “Gravity’s Rainbow”? C’mon, did you really read that? Put “Finnegan’s Wake” on here and seal the deal: these are books someone told you you should read.

  • Ken

    I want to read them one by one, good descriptions.

  • Gordon

    Apparently “cool” is synonymous with “white male power fantasies”

  • Amy

    Pretentious list of boring books. Only seem cool when your 19. Or if your a wannabe college professor at a 2 year community college.

  • molly

    i guess women can’t write cool books.

  • Sarah

    Apparently the only cool books are about war, drugs and porn…. and only written by male homophobic, white drunkards (except S.E. Hinton of course)

  • Sarag

    Lolita should be on here.

  • Bradley B.

    The Outsiders is on the list. Do you have any others?

  • Jacob Crim

    I would add Anthony Bourdain “Ktichen Confidential” to the list.

  • Anon

    You don’t know what ‘dearth’ means. Which probably explains… never mind.

  • http://lackofresponse.tumblr.com/ Patrick Batemare

    this is a very limited definition of cool that seems to revolve around drugs, violence, and a negative attitude. needs some Alan Watts for wisdom, Terry Pratchett for wit, and Grant Morrison for just plain weird.

  • Paul Donohoe

    god almighty Is this list a joke? some are okay but mostly rubbish and lead to all kinds of contradictory ideas of what “cool” means to the list maker. And where is On the Road?

  • Roland Eriks

    Nicky Cruz – Run Baby Run. Surprised to not see it on here.

    “Cruz was raised in Puerto Rico. His parents were heavily involved in Santeria, and as such, Nicky was the victim of repeated physical abuse and rejection at their hands. In an attempt to escape his violent upbringing, Nicky fled to New York City in the mid 50s where he soon got caught up in the gang violence that was sweeping the city. Fearless and seemingly immune to physical pain, Cruz rose through the ranks of the notorious Mau Mau gang in Fort Greene, Brooklyn to become their War Lord.”

  • Sarah Rohrs

    No women authors on this list. Pathetic.

  • peaceseeker.

    Dinosaur list. Times change. This is a list of violence., and it promotes the cowboy attitude so prevalent in the “gun toting society” that exists in the minds of the old white men that are , “thankfully ” a dying breed.

  • Sarah Morison

    This list is not “cool” — there are no women authors on it!

  • Sarah Morison

    Amy — time to learn the difference between “your” and “you’re”, don’t you think?

  • Sue Brooks

    Fortunately I don’t wish to be this sort of cool…so i don’t need to read all of these.
    The coolest thing is to be yourself and pick your own reading matter.

  • Franko

    Agree with many below. Lame and predictable!

  • Mags

    Can’t say I agree at all with this list…a few on this list were real turnoffs, like Catcher in the Rye… lame.