50 Books Every Man Should Read Before He’s 50

The best books for men aren’t necessarily all what you might think of as “manly.” At their core, the books that men should read (yes, even the books for men who don’t like to read) teach a lesson. Sometimes that lesson is straight forward–self help books for men that improve life and general wellbeing, for example. They’re not always the top five most read books, but sometimes they are. Some are an engaging narrative, others are straightforward advice. Some are historical and recount things like what war is really like, while others are just plain cool books. And while there are surely plenty of classics out there, there’s no shortage of new books either that can constantly be added to the list.

Consider this list of 50 as your starting off point. You might recognize a few titles from school required reading, but even if you read more than the Sparknotes you’ll want to refresh (they’re classics for a reason, after all). Jump around the list and try and complete all 50 before you’re 50. You’ll be a better man for doing so.

The Odyssey – Homer

Teachers like to think they’re introducing their students to Greek history with this book, but really what they’re giving them is one of the most violent, ridiculously unscholarly books ever written. People are bitten in half, smashed on rocks, lured to death by women-esque creatures with sexy voices, do so many drugs they stop caring about existing, and have sex with goddesses. It’s more HBO in tunics than history. That said, it is important insight into classic Greek myth making, and knowing this story will help you understand so many modern stories that have been told since.

The Lord of the Rings Trilogy – J.R.R. Tolkien

There’s a reason Middle Earth has stuck around as long as it has. Its history feels almost as rich as real history, which is impressive since it took billions of people to make ours and, like, two (mostly one) to make Middle-Earth’s. Tolkien’s linguistic expertise is the reason the books feel as rich as they do, seeing as how he invented one whole speakable language and pieces of half a dozen others. Instead of the cobbled-together feeling of lazy fantasy, Middle-Earth has rhyme and reason as its bedrock.

Dubliners – James Joyce

Joyce is hard to get into if you don’t have the patient guidance of a tenured literature professor to lead you through the rough patches. Dubliners is on the list because it’s a great introduction to Joyce’s major themes and characters, plus reading it will make it that much easier to pick up Ulysses and Finnegans Wake. Not that Dubliners is any slouching steppingstone. There’s some pretty heavy themes hiding behind the friendly Irish facade of early 20th century Dublin, and Joyce isn’t afraid to explore it.

Jurassic Park – Michael Crichton

It’s surprising that a novel that relies on the science of the time as much at this one doesn’t show its age. Crichton knows his stuff, but one of his smarter moves is only giving as much science talk as needed to suspend disbelief and not distract from the real substance of the story: the struggle between capability and culpability. Just because mankind can do something doesn’t mean mankind should do something. The book makes a pretty solid argument for ethical science, especially since not-ethical science means having your intestines pulled out by velociraptors.

One Flew Over the Cuckoo’s Nest – Ken Kesey

Watching R.P. McMurphy antagonize his way through a mental hospital is as glorious as watching a train crash into a dying star. Everyone knows this won’t end well for anyone, but there it goes happening anyway. If there’s a moral here, it’s gotta be “buck the system, but don’t buck it too hard and know when to lay low and you can always come back for more later.” Which, knowing how the 60s turned out, sounds like a decent way to sum it all up.

The Road – Cormac McCarthy

Just try and find a better father-son relationship in literature. They are the spine of this story, and everything that happens in the book is viewed through the lens of their relationship. Yeah, there’s a movie and yes, the movie is very good, but pick the book up. It’ll stick with you in a way the movie doesn’t.

1984 – George Orwell/Brave New World – Aldous Huxley

Both of these are in the same entry because everyone likes to talk about them as if they’re mutually exclusive. But consider this a bonus two-for-one look at crushingly depressing alternate history global dystopias. Both make timeless observations about the public’s relationship with its government and itself and it’s easy to think of them happening in the same world in different cities. Read them as loose warnings and not explicit predictions. It gets a little bleak otherwise.

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Fahrenheit 451 – Ray Bradbury

Fahrenheit 451 could be dismissed as the writings of a technophobe, but that wouldn’t be entirely correct. Bradbury saw the potential for abuse and placation present in television and, after seeing what’s become of popular programming and a good deal of the internet these days, it’s hard not to agree with him. It’s all bad, but maybe humanity could have listened a little better and been more discerning about what’s popular.

God Bless You, Mr. Rosewater – Kurt Vonnegut

Slaughterhouse Five is excellent, but God Bless You, Mr. Rosewater feels a bit more relevant these days. Centrally, it deals with a man who puts others above all else and the effect that has on different members of his family and community. Short version: they’re not happy and decide to do something about it. Vonnegut hits hard, but the ending to this book hits hardest.

A Confederacy of Dunces – John Kennedy Toole

Ignatius Reilly is refreshing because he’s awful in so many ways. He’s unintelligent, cocky, fat, ugly, bullheaded, verbose, repressed, and mean–and makes sure everyone knows it. You’ll find a thousand ways to hate him and everyone around him by the end. For instance, he gets his hot dog cart because he brings his signature awfulness to one of the best food delivery systems in the world. More than maybe any other book, Toole’s frustration with the world burns straight through this novel. This wasn’t a book written by a happy man.

Hard Times – Charles Dickens

Utilitarianism comes in different forms, though often not as obvious the one Dickens’s Mr. Gradgrind employs. While not Dickens’s most well-known work, it is the one that feels like it has the most to teach us in a time when economic hardship and ingrained old world prejudices keep people from exploring their potential. His presentation makes it clear exactly who the victim of Utilitarianism is, and it’s hard not to have even a small bit of personal reevaluation by the end.

The Complete Calvin and Hobbes – Bill Watterson

No one’s captured the free association and imagination of childhood quite the way Watterson has. The comics slams you with some serious, but healthy, nostalgia, regardless of whether or not you grew up in the same situation as Calvin. There’s also a serious case for Calvin and Hobbes being a collection of short stories instead of comic strips, what with continuity and storylines that run for multiple strips. If you haven’t read it at all or if it’s been a few years, pick up a copy. You’ll be surprised at how profound the comic can be in its simplicity and just how dated it isn’t.

The Plot Against America – Philip Roth

Roth’s novel explores an alternate history of the 1940s, one where FDR loses his reelection bid to the charismatic Charles Lindbergh and anti-semitic sentiment goes from whispers to official United States policy. He takes you step by step to the logical conclusion of a Lindbergh presidency and it’s a scary, highly relevant warning about the dangers of allowing prejudice to dictate who’s in public office. We’re not trying to push a political agenda here, but some of the similarities to real life are hard to ignore.

The Hitchhiker’s Guide to the Galaxy Series – Douglas Adams

The Hitchhiker’s Guide series reads like one giant novel rather than the series of five books it actually is, which is why you should read all of them. There are a thousand vignettes scattered through the series, all of them filling out what becomes a galaxy brimming with life and bureaucracy and doing it in a way that that nothing really makes sense and it was never supposed to, so let’s all just do the best we can, shall we?

Preacher – Garth Ennis and Steve Dillon

Preacher is unapologetically what it is, and that’s a drug, sex, and violence fueled tear through the continental United States. There are Irish vampires, angels and demons, miracles, weird undead sex cults, Louisiana swamp people, and one hell of a twisted Saint. But somehow, none of that distracts from the central plot line, which is one man trying to do the right thing in a world that really, really doesn’t want him to. If anything, it enhances it, making Jesse Custer’s struggle all the more human, despite him having a god in him.

Catch-22 – Joseph Heller

“War is hell,” is the old adage we all know, but Catch-22 looks to modify that a bit. Instead, war becomes super weird. The book follows a bomber squadron in the Second World War whose collective sanity is slowly being eroded by whatever passes for power. Throughout it all, the main character keeps trying to prove himself insane enough to be kicked out of the Navy, which is precisely why he can’t be kicked out. Which is a catch 22 and, yes, this is where the phrase comes from. It’s a great extrapolation of quirks and idiosyncrasies we see in day to day life, only this time, they’re affecting war.

All Quiet on the Western Front – Erich Maria Remarqu

Post World War I Europe was an increasingly disillusioned place, and All Quiet on the Western Front was one of the first books to reflect that. Up until its publication, the generally accepted way to talk about war was as a gentlemanly pursuit not unlike polo, the theatre, or other rich-people stuff. This book came around and was one of the first to openly admit that getting shot isn’t fun and that mustard gas can really put a damper on your weekend. Also, rats are terrible roommates, as are corpses.

Maus – Art Spiegelman

Maus is a hard book to forget once you’ve read it. It’s something of a saga, tracing Spiegelman’s father’s journey through both the invasion of Poland and the Holocaust. Spiegelman uses various animals to represent different groups, the Nazis as cats and Jewish people as mice, making it a suspenseful game of literal cat and mouse. It’s absolutely one of the more poignant and emotional renditions of the Jewish struggle of the 1930s, 40s, and after, and the impact it had on survivors and their children. One of the few happy notes: the Americans are drawn as dogs.

Candide – Voltaire

Candide is an 18th-century French satire, in which Candide the optimist, student of the philosophy that he lives in the best of all possible worlds, travels all over the place and bad things happen to him the whole time. There’s death, assault, disease, confusion, kidnapping, and slavery, all based on real-world historical examples. The book doesn’t actually propose an alternate to optimism, so we have to assume it just doesn’t want people blinded by some cheap mantra like “best of all possible worlds.” Which, to be fair, is a decent lesson to take away and one that more people could benefit from.

Two Pints – Roddy Doyle

Two Pints is the book version of being the regular at the local bar. It’s Roddy Doyle’s imagined transcriptions of the conversations of two Irishmen down at their local and takes you through most of the major developments of 2011-2012. It’s a short one and you could probably down two pints in the time it takes to read it. In fact, do exactly that. Make sure they’re imperial.

The Virginian – Owen Wister

It can be easy to forget why the Western genre was popular in the first place. But if you read The Virginian, you’ll see how the genre earned its popularity. It was the first of its kind and everything you’d expect from a Western is present, from shootouts to love to matching wits with the villain. Despite being more than a hundred years old, the book remains exceptionally readable and compelling and reminds you that there’s no excuse for not being a gentleman.

Guards! Guards! – Terry Pratchett

The Discworld series of novels is hard to start and more than one person’s been intimidated right out of exploring. Consider this your introduction to the world, as Guards! Guards! is the first in the Night’s Watch series. You get a really solid starting point that gives you everything you need to know about the world, wrapped up in a funny, genuine, and unexpectedly exciting story.

Lamb: The Gospel According to Biff, Christ’s Childhood Pal – Christopher Moore

You’d think it wasn’t possible to avoid blasphemy and sacrilege while writing a postmodern interpretation of the Gospels, but Moore does it. This book is both exceptionally funny while staying respectful of its source material. An argument would be made that this book actually enhances the Christian Messiah’s character, since we get to see him at every stage of his life, exhibiting an excellent understanding of the human condition. What’s more, Moore’s rendition of the crucifixion is well-crafted and legitimately heart wrenching.

That Thing You Do With Your Mouth – Samantha Matthews and David Shields

It’s difficult to be as open about yourself as Matthews is in this book. It serves as an extended monologue, so basically Matthews talking (which is where the title comes from), about her sexual past, a past that wasn’t the fairytale most people hope for. There’s a lot to learn from what she has to say, and it’s never hurt to get some different points of view.

No Matter the Wreckage – Sarah Kay

Sarah Kay’s second collection of poetry is something special. She constructs some of the most relatable and accessible poetry this side of Post Modernism while never sacrificing substance for style. What’s more, Kay makes a genuine effort to connect with her reader, something that it seems a lot of other poets gave up a long time ago.

Fear and Loathing in Las Vegas – Hunter S. Thompson

“We were somewhere around Barstow on the edge of the desert when the drugs began to take hold.” So begins Hunter S. Thompson’s most famous work of gonzo journalism. Based on two trips the good doctor took with his attorney to Sin City, Fear and Loathing in Las Vegas blends fact and fiction into one hazy tale. You can get a contact high just from reading it.

My Struggle (Series) – Karl Ove Kausgård

To the uninitiated, Karl Ove Kausgård’s six-book series can seem like a joke. Here’s a guy who’s led, for the most part, a pretty normal life. There were troubles, yes, but none that would make you take pause and feel incredibly sorry for him. And yet, he went ahead and wrote close to 4,000 pages on that fairly standard life. Then you read it. Drawing comparisons to Marcel Proust’s In Search of Lost Time, Kausgård’s books highlight the mundane, the relatable, and the business of being a human. It’s brilliant, and it will make you want a cigarette.

The Great Gatsby – F. Scott Fitzgerald

This is one of the few that forced school summer reading gets right, so if you skipped it in school, find yourself a copy now. It’s not a long read, if that makes a difference to you, but man is it dense. At the surface, it’s an interesting story about a guy’s cool but manipulative neighbor. Further down, it has something to say about almost every single human vice. Reading it, the Great Depression seems completely unavoidable.

The Catcher in the Rye – J.D. Salinger

The Catcher in the Rye is one of those books that should be read once every 10 years, at least, thanks to the changing way the reader views the main character, Holden Caulfield. When you read it at 14, Caulfield is a visionary and one of the only characters to truly understand what you’re going through. At 24, he’s a stupid, whiny kid who then makes you angry at the stupid whiny kid you used to be. At 34, you hope that you never have kids like him, and at 44 you’re just happy your eyesight is still good enough to read this without glasses.

The Sun Also Rises – Ernest Hemingway

Trying to select one Hemingway book for this list is like Hemingway trying to select one drink from the bar—they’re all too damn good. Even still, The Sun Also Rises stands out. The novel, which was published in 1926, tells the tale of a group of expats on their way to Pamplona by way of Paris. Much like A Moveable Feast, one of the real highlights is Hemingway’s ability to tantalize you with cafe culture and conversation that happens over shared drinks.

The Things They Carried – Tim O’Brien

Tim O’Brien’s collection of short stories focuses on the men involved in the Vietnam War rather than the political division of the American home front. There’s a deep sense of tragedy about the book that O’Brien pushes one step further by making the reader constantly question how much of the book is true and whether or not it even matters. If these aren’t true events, are they still tragic? Or does the tragedy become true through the reader’s emotional response? It’s a great tool for dispelling some of the more venomous myths about the Vietnam War while also humanizing the guys who were sent over.

Naked Pictures of Famous People – Jon Stewart

Jon Stewart’s time on The Daily Show was so influential and powerful it’s easy to forget he pursued things outside of TV. He was in a few movies, did a lot of standup, and wrote things that weren’t TV scripts. One of those things was Naked Pictures of Famous People. It includes short stories, essays, scripts, and lists that show off a ton of talent, not just the political satire he’s known for.

My Documents – Alejandro Zambra, translated by Megan McDowell

International authors aren’t talked enough about a lot in the broad American audience, but Zambra’s work makes a compelling argument for seeking out translated work. My Documents is a book of short stories, written originally in Spanish and translated flawlessly by McDowell, and allows American readers to explore the similarities and differences, both more subtle than you’d think, between life in the United States and Chile. While reading, you often have to remind yourself that the stories are taking place in South America and not the more residential sections of New York City or the like.

To Kill a Mockingbird – Harper Lee

Harper Lee’s book is often people’s first introduction to race relations, criminal justice (or lack thereof), and the neighborhood weird guy. It may also be a slight indictment of modern America that most of the specific problems the characters face are still present today, especially since the story is set in the 30s, was published in 1960, and feels like it could have been written yesterday. It’s unlikely that you haven’t read it, seeing as how it’s one of the most widely-read books in the country, but if you haven’t, it’s not too late to catch up. Link

The Táin – Translation by Ciaran Carson

Seamus Heaney, a name you’ll recognize from your favorite version of Beowulf, loved this translation of The Táin, the ancient Irish epic, so that alone should be enough for you to pick up a copy. If you need more, the text starts with an Irish king and queen bragging about their kingdoms post-coitus and when they find out one has a better bull than the other, they start a land war which is repelled by a single 17-year-old and his charioteer. So it gets weird. It also shows that ancient poets might not have taken themselves as seriously as we thought. They were entertainers, after all.

The Brief Wondrous Life of Oscar Wao – Junot Díaz

One of the reasons The Wire is often considered the greatest television show of all time is the fact that the dialogue feels authentic. It’s an incredibly difficult thing for a writer to master. Junot Díaz conducts a clinic on it in The Brief Wondrous Life of Oscar Wao, his Pulitzer Prize-winning novel. Set in Paterson, New Jersey, the story centers on the struggles of a nerdy, overweight Dominican boy as he grows up in Jersey. The story is narrated by a character named Yunior, who—and this is where Díaz shines—speaks in an eloquent yet street-wise manner. Slang can often feel fake and dated if the author is not plugged into the culture, but Díaz proves that, when done right, it adds a level of believability that can make a story soar.

The Corrections – Jonathan Franzen

Few novels capture the anxiety and despair of what many would call a fairly standard life like The Corrections. In it, Jonathan Franzen paints the picture of a family that, while not exactly the same as yours, feels recognizable enough. Then, through the actions of each of the Lamberts, he takes a microscope to the fears and troubles that reside deep inside you. The Lambert children are trying to make it on their own in East Coast cities far from their parents, but each encounters issues either financially or in their relationships. Back home things aren’t much better. It’s the pre-9/11 anxiety book that nailed it better than many post-9/11 anxiety books.

Walden – Henry David Thoreau

There has been renewed interest in Henry David Thoreau’s classic, thanks to the rise of the modern-day outdoorsman. Walden is a meditation on life, simplicity, and growth. It documents the slightly-more-than two years Thoreau spent secluded in a cabin by Walden Pond. During that time he connects with nature, ponders the direction civilization is going, and lives a life like a hermit. Even if you only have a good-looking axe on display, the book is thought-provoking and inspiring, perhaps even more now than when it was originally published.

A Good Man Is Hard to Find – Flannery O’Connor

Flannery O’Connor might have the finest throne in the pantheon of great short story writers, and the work that best explains why is A Good Man Is Hard to Find. Obviously it includes the legendary story of the same name, but it also includes nine other stories just as good. A theme of spirituality ties all the tales together, as many of the main characters question their beliefs when confronted with horror and abrupt change. In each of the flawed characters you can find a little bit of yourself, and O’Connor was beyond skilled at driving that home.

The Amazing Adventures of Kavalier & Clay – Michael Chabon

The Amazing Adventures of Kavalier & Clay is a sprawling historical novel packed with heavy topics—the plight of being Jewish in certain parts of pre-WWII Europe, the struggles of being gay in America at the same time, big business swindling. What makes it so brilliant, so enjoyable to read, however, is the air of levity Michael Chabon applies. It’s done, in part, by the childlike innocence of the main characters and also by the fact that it’s a story about superheroes, comic books, and the age of wonder.

East of Eden – John Steinbeck

Steinbeck is probably best known for The Grapes of Wrath and Of Mice and Men. However, East of Eden is his finest work. In fact, Steinbeck would probably agree. Upon completion of the 690-page tome, he wrote to a friend, “This is ‘the book.’ If it is not good I have fooled myself all the time. I don’t mean I will stop but this is a definite milestone and I feel released. Having done this I can do anything I want. Always I had this book waiting to be written.”

White Teeth – Zadie Smith

Books like White Teeth don’t come around often. First of all, it deftly handles complex themes like race and immigration. The feelings, emotions, and challenges the characters face in relation to these things feel real, powerful, and, at times, excruciatingly brutal. Second, while it’s moving for that reason, it’s also a joy to read. Zadie Smith’s writing is stunning and witty. There is a bit of humor throughout, a bit of fun that makes the sorrow cut even deeper. By using multiple viewpoints, Smith not only displays her skills for fleshing out characters, but also gives you, the reader, different vantage points on assimilation. It’s the rare ambitious novel that really works.

Crime and Punishment – Fyodor Dostoyevsky

This is the type of book that you could spend countless hours creating a chart of character names to remember and struggling with relationships. Instead of War and Peace, allow yourself the journey into Crime and Punishment, Dostoevsky’s tale of moral struggles. The story, which was originally published in 1866, is about Rodion Raskolnikov (you’ll want that name on your chart), a man who decides to kill a seedy person and make off with their loot. He justifies this by saying he’s taking out a bad person and doing good with his money. A win-win, right? Like most Russian works of the time, it resonates on a philosophical level while still being an example of great storytelling.

Between the World and Me – Ta-Nehisi Coates

On occasion, a book will come along at just the right time to dissect the climate we live in. It will put into words—beautiful, eloquent words—the thoughts floating around in many of our heads. These books often go down in history as seminal works. Perhaps there is no greater recent example than Between the World and Me. Penned by The Atlantic writer Ta-Nehisi Coates as a series of letters to his son, the book deals with race relations in America today. As a Black man, Coates shares some painful truths, emotionally-moving fears, and even some hope with his son. Simply put, it’s important you read it.

Infinite Jest – David Foster Wallace

Here are a list of things you may find less difficult than reading Infinite Jest: solving a Rubik’s Cube, beating Joey Chestnut in an eating contest, The New York Times Saturday crossword puzzle, teleportation. Yes, Infinite Jest can be challenging, at time laborious, and often confounding, but there is beauty in all of this. In fact, the “postmodern encyclopedic novel,” as it has been described, is best consumed as a meditation on such things as addiction, mental illness, depression, family, and much more. The story(s) take place in a dystopian future, where the United States, Canada, and Mexico have joined one large North American nation. Each year is sponsored by a specific corporation, resulting in things like the Year of the Tucks Medicated Pad and the Year of the Whopper. There’s tennis. Lots of tennis. Like we said, it’s weird, it’s confusing, but it’s also brilliant.

Pastoralia – George Saunders

There are few short story writers working today more revered than George Saunders. He builds stories around down-and-out characters who find themselves in ludicrous scenarios. But the true brilliance of Saunders is the way he uses these stories as a means to comment on contemporary life. It’s satire, yes, but it feels unique and distinctly Saunders. It’s like he sucks the emotion off the page and allows you to insert it yourself. In Pastoralia, his collection released in 2000, he gave us six stories that all originally saw publication in The New Yorker. Four of those six stories won an O. Henry Award, which is given to stellar short stories. It’s the ideal place to start on your wonderfully weird and poignant George Saunders journey.

Dune – Frank Herbert

So you want to get into sci-fi but don’t know where to start. How about with one of the best-selling sci-fi books of all time that also happens to be extremely approachable? Dune, the first book in the Dune saga, by Frank Herbert is a futuristic tale of planetary ownership and warfare. You know, standard sci-fi stuff. But where it departs from the heavy, techy sci-fi you might be envisioning is in how Herbert removes those stereotypical robots, computers, and other elements to simply tell a political tale that resonates on a very real level. Plus, you’ll understand the movie much (much) more if you read the book.

2666 – Roberto Bolaño

Roberto Bolaño’s final novel is not for the impatient. At over 900 pages, it isn’t exactly a beach read. What 2666 is, however, is Bolaño’s magnum opus, a final work that adheres to only the writer’s rules. Yeah, it gets a bit wild and surreal. At its most basic, though, the novel, which Bolaño wrote during the final years of his life as his health declined, is about the murders of women in a city named Santa Teresa, based on the real-life city Ciudad Juárez. Broken down into five parts (Bolaño originally planned on releasing five separate books to provide more wealth for his offspring), the novel showcases Bolaño’s skills at creating the hostile atmosphere and anxiety of a place, much like he did in The Savage Detectives. The slang is smart, the unease painful, and the words a joy to consume.

A Visit from the Goon Squad – Jennifer Egan

Existing in a world somewhere between novel and short story collection, Jennifer Egan’s A Visit from the Goon Squad is truly a unique work, though you probably could have guessed that upon hearing her two sources of inspiration for it: Marcel Proust’s In Search of Lost Time, and the HBO series The Sopranos. Though the stories feature a collection of main characters that appear, disappear, and then reappear again, each chapter/story has its own distinct feel, though almost involve some aspect of the music scene. What Egan accomplishes is something special—a “novel” that feels as free and loose and beautiful as a Woodstock jam session.

I am Legend – Richard Matheson

You almost definitely recognize the title from the 2007 Will Smith movie based loosely on the book (emphasis on “loosely”). Not that the movie wasn’t good (up to a point) in its own right, but the book gets much more into the philosophy of Robert Neville’s actions and convictions, the world feels more fleshed out, and the line between hero and villain isn’t so bold. Plus, in the book, the title makes way more sense.