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.

    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.

    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.

    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.

    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.

    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.

    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.
    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.

    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.

    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.