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)


  • Bryan

    26 (or higher). On the Road – Jack Kerouac

  • JP

    Holy crap I’m so impressed that you didnt include On the Road! Kudos to you guys for not including that washed up frat boy goes on walkabout crap book!

  • Carl Plumer

    I’d add Wolfe’s Look Homeward Angel; Elison’s Invisible Man; anything by Conrad; and then there’s a personal favorite, Melville. No one was ever cooler than my man Ishmael. Go ahead, call his name. But don’t wear it out.

  • fctorino

    This list is missing one ingredient: life affirming books. Most of this list confirms what the rest of humanity knows: life is mostly miserable, and people are mostly miserable to each other. Surely you could have had a place for at least one book that affirms otherwise. How about some Marilynne Robinson?

  • aaugust

    10 out of 25…have some reading to do..

  • MyPeace

    These are all the bull s!!t bokks we were made to read in school — and they still suck!

  • mph23

    “Define cool”? More like define “hipster douchebag who thinks he knows about literature, life, and the universe because he took a class”.

    I haven’t read everything on this list, but the ones I have are overrated big time. Try reading some Camus, Calvino, and Clarke (sorry for all the C’s, lol).

    Even better, read whatever fiction YOU enjoy; not just what people tell you is ‘mind-blowing’ ‘cool’ or ‘important’. As for non-fiction…Read some fucking non-fiction.

  • Tom?

    Add “Soon I Will Be Invincible” to this list. Remove “Catcher In The Rye”. Holden was an awful person and a spoiled brat.

  • lucid

    Had you read them, or anything for that matter you might know how to spell books. Cheers to ignorance

  • Q

    Any of Ian Fleming’s Bond books are cool. Obviously its not the intellectual choice like a few of the above, but you can’t top 007 for cool factor.

  • Sara

    I would definitely add The Stranger by Albert Camus

  • Ollie

    BUKOWSKI ???????

  • Robin Austin

    This list pisses me off for its lack of female authors. I love many of these books but Arundhati Roy’s “God of Small Things” belongs here, as well as at least a dozen other women authors

  • Jim Spahr


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

    Indeed, it’s a list by a definite Hipster. To boast the “cool” factor is idiotic. The only surprise was Kerouac’s On The Road wasn’t in here.

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

    Seriously, “cool” books?! What moronic Hipsterism. It’s either a good book or not. I would imagine these authors would be appalled at being included here. When I read I don’t sit there smugly thinking, “I am so cool and macho!” Mindless narcissism. I read to indulge in great culture, for enjoyment and escapism, and to learn things.

    Still, if you want to feel “cool”, try some of these writers:

    Sartre, Solzhenitsyn, Kurkov, Orwell, Steinbeck, Camus, Plath, S. Buck, Philip K. Dick.

  • trxr

    Eh, I wouldn’t bother including them in this list of books that mainly appeal to adolescent pretentious douchebags under the age of 25. It’s not about the *quality* of the writing, as such (although some of these are excellent books).

  • alex

    A Fan’s Notes by Frederick Exely

  • Josh

    Fight Club? hahahahahahahaha!
    Nice list of white dudes, bros.

  • adolescent pretentious douche

    YOU’RE a douchebag.

  • Firmin

    “The Third Policeman” by Flann O’Brien? Sure worked for me (in a Sartre-like kinda way).
    And yes, there should have been more female authors, including Alice Munro. If only because she is indifferent to “cool”; which of course ironically epitomizes cool.

  • Firmin

    I was a little curious about the “Sort by Best” option and thought I might give it a try. I’ll admit to being a tad surprised that “YOU’RE a douchebag” scored so high with the “judges”. Was it the terse brevity of the sentiment that so appealed to them or is “douchebag” just considered to be a particularly cool word?

  • OOgly

    Pretentious crap

  • Hiro Protagonist

    Snow Crash isn’t on here. This list is invalid

  • Gina222

    An uncool article….

  • kmanthie

    Where is NAKED LUNCH? JUNKY? NOVA EXPRESS? (or ANY William S. Burroughs books?) AND Where is James Joyce: ULYSSES? FINNEGAN’S WAKE? And I know it’s become almost a cliche, but you don’t even have ON THE ROAD, which, overhyped or not, is not the fault of Kerouac. It is written in the most unique prose – a jazzy rhythm to the cadence, But, to not even have NAKED LUNCH or JUNKY on here shows that there was wayyyyyy too much focus on post-post modernist, derivative stuff on this list. I agree that BLOOD MERIDIAN is a very well-done book, as is GRAVITY’S RAINBOW, which is kind of like the post-modernist ULYSSES. But why not have the original ULYSSES??

  • kmanthie

    You can’t just stick a book in a list like this for the sole purpose of “affirmative action”, i.e., getting a woman in it. Of course, there are plenty of great women authors, like Joyce Carol Oates or Susan Sontag, who could’ve been on here or Virginia Woolfe, for example, but the latter might be considered too “dated” for an audience that, it’s assumed, isn’t that well-versed in literature to know who Woolfe was. And, if we include poetry, there could be Emily Dickinson, one of the best poets to have come and gone. Besides the aforementioned female writers, there are so many missing books that one could consider “hip”

  • kmanthie

    Some of these books also don’t really fit into the category of “cool” or even “hip” – I mean, why is Machiavelli considered “cool”?? THE PRINCE was a masterpiece and is a sort of manual for how to scheme and plot to get to a desired end, particularly in the realm of political power and statecraft, but I say that it’s “cool” – the same thing w/THE ART OF WAR – why is this cool?? What is COOL about it? It’s basically a flowery-prose-filled textbook on how to defeat your enemies. If this is “cool” then why isn’t Clausewitz’s ON WAR, the Prussian 18th century equivalent, on this list? If your intention was to be culturally diverse and have an ancient Chinese text on here that comes at least somewhat close to “cool”, why not pick TAO TE CHING, credited to Lao-Tzu (but widely thought to have been written by a sort of “consortium” of like-minded Chinese writers from the time period whence it came). If this list was supposed to represent “cool” books, it fails to include many books that were, indeed, “cool” or “hip” (‘hep’) and instead you mistook literary classics and well-known texts that are not “cool” (unless you’re a pasty-faced right-wing reactionary).

  • kmanthie

    YES. Bukowski – Charles Bukowski was a brilliant writer of novels and poetry who lived in Los Angeles but was born in Germany (his family moved to LA when he was a young child). His works include such titles as POST OFFICE, TALES OF ORDINARY MADNESS, PULP, WOMEN and many. many others. Go to your library and see if you can find anything of his there or else buy his stuff on Amazon or at your local independent bookstore.

  • kmanthie

    What about the absence of William Burroughs? Everyone “cool” has had their photo taken w/Bill up until when he died. Bukowski, Sartre? There’s an endless amount of stuff that could’ve been on here instead of the mediocre things that are on here (there are some genuine “cool” items, but not all are).

  • kmanthie

    You’d have to be insane to omit CATCHER IN THE RYE – that is a cult classic – you really can’t get much cooler than Holden Caulfield, a literary archetype that has gone on to define generations. If you think Holden was a “spoiled brat” then you, obviously a) haven’t read it or b) didn’t understand it at all.

  • kmanthie

    Ha ha ha ha ha!! Good one! Also – the only book on this list I read in school was CATCHER IN THE RYE, which I’ve re-read many times since. I doubt if any high school teacher would have his or her students read-or even try to read-GRAVITY’S RAINBOW(!!) You might as well expect them to read and understand ULYSSES by James Joyce!!

  • Adam

    Read the details on number 24 again. It may be only one, but that is distinctly different from a “lack”.

  • Ren

    They’re Eyes Were Watching God, Jane Eyre, The Awakening, The Heart is a Lonely Hunter, and The Bluest Eye are missing…

    Is there something those authors have in common??

  • R. Archer

    I appreciate the writer’s effort, but the article seems to be more of a list of pet “cool books” than “books that define cool.” it includes books that – while good – don’t define cool at all (The Art of War, The Prince, Walden, All the King’s Men). It excludes books that set the tone for what was considered “cool” – especially masculine cool – in post-WWII America. I’m thinking of the mystery/thrillers (Hammett, Chandler, Spillane, John D. McDonald, Fleming), the Black American experience (Ellison, Wright, Himes, Baldwin, Cleaver, Malcolm X), the Beats (Kerouac, Burroughs, Ginsberg, Corso, others), the pre- and post-war French (Gide, Sartre, Camus, Malraux, Genet), and the post-beat Sixties (Mailer, Richard Farina, Terry Southern, Kesey, Watts, Leary, Castenada, others). Some books by women writers (e.g., Rand’s “The Fountainhead” and Joan Didion’s “Play It as It Lays” might also edge out some of the selections on the list.

    For me, the weak representation of the Beats and the mystery/thrillers was a big miss for this list. For better or worse, Jack Kerouac’s “On the Road” defines Beat coolness; and Raymond Chandler’s “The Simple Art of Murder” gives a very specific definition of masculine cool: “Down these mean streets a man must go who is not himself mean, who is neither tarnished nor afraid.”

    Sorry if this all sounds pretentious, but it’s kind of hard to talk about “cool” without sounding stuck up in some way. Heck, even using the word “pretentious” sounds pretentious. Be cool.

  • Madhava Verma Dantuluri

    Excellent list.

  • http://pirancafe.com/ Bob R

    Not here to argue, because that would be pointless and uncool, but rather just to say that I own 17 of these, and of those have read 14. (Leafing through The Art of War not included.) That makes me just over half cool, dangerously close to nearly tepid.

  • Adventures


  • lefauxfrog

    Don’t read to be cool. Don’t hope someone will spot you reading one of the books that’s supposed to make you look cool. Read what you want.

  • Mickey

    I am 100% sure the Outsiders is by a woman. It’s one of my favrite books and I am not an under age douchebag. I am somebody who loves books.

  • Chris

    Couldn’t agree more! For starters, where is Edith Wharton’s “The House of Mirth,” as splendid a candidate as I can think of to adorn with the title The Great American Novel?

  • Chris

    YOU’RE an adolescent!

  • Chris

    Yes, it’s written by a woman. Sadly, it pales beside the work of other female writers omitted from this faulty list.

  • Chris

    Camus is probably the most pretentious, self-worshiping author who ever lived. I’d pick Pynchon as a close second.

  • Chris

    On the Road may be brilliant, but it’s also the most depressing book I’ve ever read.

  • Chris


  • Chris

    Speaking of death by overexposure — doesn’t ANYBODY read Steinbeck’s “The Grapes of Wrath” anymore? Who cares if none of his other work came close to this still-vibrating novel? It’s virtually the only book I can think of that serves equally as a wrenching probe of common-man despair and as a thunderous political call to oust the fatcats. Three-quarters-of-a-century later it still delivers the goods — heroically.

  • Chris

    Indeed! How ABOUT some Marilynne Robinson — acolyte to the notion that life may be miserable but absolutely worth living, and probably our best female author. (Though alas far from our most prolific.) “Gilead,” anybody? Please?

  • Chris

    Shouldn’t you have included James Ellroy among the hippest of the hip? And certainly among the most unsettling!

  • Chris

    “Native Son,” anybody? A shameful omission.