25 Books That Define Cool

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

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1. the sun also rises (ernest hemingway)

this list could easily include almost everything papa hemingway wrote. his concise style and penchant for alcohol are common throughout his catalogue. however, if we had to choose one, we would go with the sun rising too. 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 remains as important today as it was to warriors 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 a little brains to a clash of strength. today, its applications extend far beyond the battlefield as required reading for modern businessmen and intellectuals. (link)

3. fear and loathing in las vegas (hunter s. thompson)

Honestly, I could put just about every good doctor’s book on this list (hell’s angels and the rum diary come to mind), but if I had to pick one, it has to go with fear and loathing in las vegas and all his drug fueled madness. If you’ve never read it, the opening sentence should give you a good idea of what to expect: “We were somewhere near Barstow, on the edge of the desert, when the drugs started to take hold.” Long live gonzo journalism. (link)

4. slaughterhouse-five (kurt vonnegut)

there have been many war books published in recent years and many are very, very good, some even make a strong case against war without just stating the idea (see: billy lynn’s long half time walk), but none of these can do what slaughterhouse-five did. vonnegut accomplished something so strangely amazing that he wrote a light-hearted and easy-to-read, yet incredibly moving and dark book. (link)

5. trainspotting (irvine welsh)

You’ve probably seen the movie, but have you read the book it’s based on? it’s one of the rare cases where both are fantastic. He’ll take a little getting used to Welsh’s handwriting, and he’ll probably be speaking with an accent inside his head, but once he gets the hang of it, he’ll embark on a grittier ride than even the movie could provide. (link)

6. walden (henry david thoreau)

With the renaissance of nature lovers right now, it’s good to look back at one of the books that probably started it. Walden is not the boring one you read about in high school, it takes time to appreciate it like a good bottle of red. Thoreau’s masterpiece tackles many things while quietly activating your brain. it also makes you want to build a cabin. (link)

7. blood meridian (cormac mccarthy)

blood meridian paints a picture of brutality that no movie could match. While McCarthy has plenty of worthy candidates for this list (see: The Road and No Country for Old Men), we still think Blood Meridian is his best work. the story centers on a group of bounty hunters and the boy, a rebellious teenager who joins the group, as they hunt down Indians. Although that is the story, the real focus of McCarthy’s work is violence and that little seed of evil that we all carry inside. (link)

8. the rainbow of gravity (thomas pynchon)

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

9. rabbit, run (john updike)

The best midlife crisis novel of all time isn’t really about midlife crisis. Harry “Rabbit” Angstrom is 26 years old when he decides to leave his wife and son for a new life. Of course, what this new life is and what exactly he wants from it is not clear to the reader or to the rabbit himself. he will strike a chord with all the men who struggle with the idea of settling down. (link)

10. fight club (chuck palahniuk)

chuck palahniuk did not enter the literary scene quietly, he kicked the damn door down. fight club was his first and best known work. even if she has seen the movie, which she probably has, she is doing herself a disservice by not reading the book. one of the movies that defines cool also happens to be one of the books that he does too. The novel is so original, so thought-provoking, and so maddeningly brilliant that you’ll want to get copies of Survivor, Strangler, and Palahniuk’s other works. (link)

11. all quiet on the western front (erich maria remarke)

if all the silence on the western front didn’t have the ability to stop the war, no book will. the author drew on his wwi experiences and put together one of the best-known war books of all time. the story is of a fresh-faced German soldier facing the trials and tribulations of training and the horrors of battle. the entirety of the soldier’s experience is captured without the author turning a blind eye. (link)

12. the amazing adventures of kavalier & clay (michael chabón)

the amazing adventures of kavalier & Clay appeals to the kid in all of us who wants nothing more than to be a real-life superhero. It’s great, because, no matter how macho or seemingly tough, every man has wanted to escape at some point. oh, also because it’s brilliant. (link)

13. the catcher in the rye (j.d. salinger)

yes, it’s a cliche choice, but the catcher in the rye has to be on this list. roll your eyes because you think you’re too cool and it’s too conventional, but the catcher in the rye is the quintessential “cool” book. teenage rebellion at its finest. (link)

14. the professional (wc heinz)

Any book that can claim hemingway is a fan is worth checking out if you ask us. the pro is about boxing, but it’s really about what separates the pros from the impostors and taking care of a trade. the story moves slowly, and in that slow and meticulous pace is its brilliance and power. (link)

15. all the king’s men (robert penn warren)

an all-time classic full of mud from politics and life. Loosely based on the story of Huey Long (former Governor of Louisiana), All the King’s Men is not only poetically written, but also gripping and hard to put down. the story goes round and round without losing strength. We suspect there’s a copy 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 verge of destruction. Beneath the Volcano is about the struggle each man faces against the beasts that trap him. (link)

17. last exit to brooklyn (hubert selby)

the genius of last exit to brooklyn lies in its rawness and reality. raises a veil that refuses to drop. the book takes you inside the seedy underbelly of an American city and pushes 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 together perfectly. Patrick Bateman, a wealthy and handsome New Yorker, spends his afternoons plotting death and murdering his associates. he approaches subjects as if it were a modern and elegant work of dostoevsky. (link)

19. bright lights, big city (jay mcinerney)

Few books capture the feel of New York like bright lights, big city. it somehow offers that vastness of being in the city when you’re young and struggling. oh, and he has a lot of drugs. (link)

20. tropic of cancer (henry miller)

was porn before porn was porn. any book that was banned for decades has a certain cool appeal, and while Tropic of Cancer might have been raunchy at the time, it’s actually surprisingly honest. He was truly ahead of his time. (link)

21. the adventures of huckleberry finn (mark twain)

The first great American novel made young people want to pull out a pocket knife and seek adventure outside of a television screen. Among the social themes it tackles is a story about adventure and growth. (link)

22. in the air (jon krakauer)

If you’re familiar with Krakauer only through the movie adaptation of Into the Wild, you really need to read this book. It is a first-hand account of a deadly trek up Mount Everest. is a gripping narrative that showcases the sheer brutality of survival. man against mountain, although the man does not always win. (link)

23. the prince (Niccolo Machiavelli)

because few things are as great as power. is the leadership book before there was a shortage of business writers filling the shelves of barnes & noble. If you want brutal honesty about what it takes to be a successful leader or political powerhouse, the prince still holds his own today. (link)

24. the strangers (s.e. hinton)

the outsiders is timeless. Replace the greasers and socs with modern cliques and gangs and the sentiments still ring true. the author was only 16 when she wrote it, so the emotions are more real than someone remembering her teenage angst. Just because it was required reading in high school doesn’t mean it’s not great. (link)

25. code tree (jonathan safran foer)

There’s something cool about doing your thing, and with the code tree, jonathan safran foer has done just that. while everything is lit up and extremely strong and incredibly close they are masterpieces that have a sense of uniqueness, they don’t come close to what the author did in the code tree. He takes his favorite book, Crocodile Lane by Bruno Schulz, and cuts out lines, words, and pages to create his own unique narrative with what’s left behind. it is both book and art. (link)

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25 Books That Define Cool | Cool Material