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The 26 Most American Books of All Time
Making appearances: at least three presidents, a handful of Pulitzer prize winners, a white whale, and a very nice pig.
By In a world where short-form video rockets across the world in seconds, journalism is shifting rapidly away from written reporting to “storytelling” on podcasts, and, chrissakes, robots are doing most of the writing, it can be easy to forget that for most of this nation’s history—all of it, we’d argue—what could really command the American culture’s attention was a thing called a book. The original long-form. Tens of thousands of words ejected from an artist’s mind after a lengthy, often painful process of research, meditation, and incessant scribbling.
How would we understand ourselves without Washington Irving’s The Sketch-Book (whence come “Rip Van Winkle,” “The Legend of Sleepy Hollow,” and essentially our entire pre-roundball understanding of Knickerbockers), Walt Whitman’s Leaves of Grass, F. Scott Fitzgerald’s The Great Gatsby, Joan Didion’s Slouching Toward Bethlehem, or Tony Kushner’s Angels in America? We wouldn’t. The answer is we wouldn’t.
So for this 250th year of our great nation, Esquire has compiled a list of our Most American Books. A few ground rules. The first and most obvious: This isn’t a list of best books, favorite books, or books you must read before you die. It’s books that exemplify America. Next: No short stories, no collections of essays, no poetry, no plays, no graphic novels. These are all wonderful art forms, to be sure. But, frankly, we needed a way to narrow our efforts to comb through 25 decades of literature. Third: This isn’t the syllabus for your high school English class. We crossed off the usual suspects, because you’ve already read them and because if your 11th-grade homeroom teacher already told you a book is essential reading for an inchoate American citizen, what do you need us for?
The upshot? Well, first of all, those rules mean everything in the second paragraph of this introduction is out. But more important, they mean that the list that follows is sure to contain at least a couple books you haven’t read, maybe haven’t even heard of, and that undoubtedly will make you see the country in a fresh, new way.
In the early 19th century, Noah Webster set out to standardize the English that was spoken in the new American republic and in the process endeavored to streamline the spelling of words. He removed remnants of some of the language’s French roots in favor of reflecting the way words were being pronounced by modern speakers—colour became color, theatre became theater. With his dictionary, Webster sought to galvanize Americans as their own people, not merely a rebellious offshoot of England but a fully realized nation with a culture all their own. In doing so, he also kicked off the grand tradition, alive and well today, of Americans and Brits arguing over whose is the “correct” English. —Connor Sears
With our unmatched capacity for vanity and idolatry of wealth, America has produced so many useless autobiographies and memoirs in her 250 years. The antidote is Frederick Douglass’s Narrative of the Life of Frederick Douglass, an American Slave. Yes, you should read it as an essential historical account of the horrors this country is capable of committing. But you should also read it as the anti-autobiography. It has no interest in personal mythmaking or fame. In the straightforward telling of his life before freedom, Douglass’s story not only details his striving for self-determination but honors all the lives—nameless, unexalted—that never got a say in their contribution to this country. —Luke Guillory
The loftiest precincts of American letters have long regarded Moby-Dick as among the most prestigious literary novels in the American canon—but don’t hold that against it. Pop open a beer and give it a read (well, you may need a few). Herman Melville’s masterwork is at once a gripping tale of adventure and a deeply knowing study of human nature and the American character. Like a beer, it needs to be savored. Ishmael, Starbuck, Queequeg, Ahab: The names alone resound like incantations. The story of the Pequod, its monomaniacal captain, and its unforgettable crew is a parable of the country and the first global economic sector it would come to dominate—tiny Nantucket was the epicenter of the world’s whaling fleet—and it tells the human cost of the vast fortunes made there, prefiguring the epic American stories of oil, steel, Hollywood, the automobile, all the way up to Silicon Valley. It’s also very funny. —John Kenney
Ulysses S. Grant wrote his memoirs the same way he fought the Civil War: The effort required everything he had, the stakes were unbearably high, and a good outcome was uncertain until very near the end. At the close of his life, stricken with agonizing throat cancer, Grant composed his memoirs over the course of a few months at the urging of his publisher, Mark Twain, racing against the clock to finish the manuscript and rescue his family from financial ruin, finishing just days before he died. The resulting two-volume work was an instant best seller, and it hasn’t been out of print since. It’s an extraordinary piece of American literature, told in prose marked by a distinctly plainspoken, direct intelligence. The books offer an indispensable firsthand account of the most harrowing and tumultuous time in American history, with Grant’s testimony to posterity about his motivations, decisions, and actions at the very center of it all. Finally, and not least, his memoirs are fascinating for the details of everyday life in 19th-century America that bubble up throughout. The story of Grant’s Ohio boyhood alone is striking and wonderful, and the account of his youthful attempts at horse-trading reads like something out of, well, Mark Twain. —John Kenney
If you truly want to understand this country, you need to read this book. To tell his story Mark Twain threw down a marker to the lettered world by choosing—and reveling in—full-bore American vernacular, rendering natural language just as it was spoken on the banks of the Mississippi, from the opening moment on through: “You don’t know about me, without you have read a book called ‘The Adventures of Tom Sawyer,’ but that ain’t no matter.” (Even to this day, goddamn auto-spell-check is highlighting that ain’t on me.) Then there’s the straight line from Huck Finn to Holden Caulfield to Bart Simpson, avatars of deeply American notions of bucking authority, embracing individuality and authenticity, resisting the hypocrisy of “sivilized” society. And of course, most important, there’s what’s at the heart of this tale of a southern white youth floating the Mississippi on a raft with runaway slave Jim, the two of them on the lam together: race. The deep friendship that develops; Twain’s depiction of Jim’s great humanity while at the same time portraying him in broad, reductive racial tropes; Huck’s ultimate moral choice; and, finally, what to make of the author’s prodigious use of the most potent racial slur in our history—all these elements have fueled discussion and dissection and reaction and deep reflection for a century and a half, since just about the moment the book was published. Read it and join the national discourse. —John Kenney
Black American life and culture is as distinctive and vivid a presence in this luminous book as the main character, Janie, whose yearning for a life containing the spark of love takes her through two hard marriages before she finds Tea Cake, who’s not right for her in every way except the one that matters. The novel’s themes—of pushing against societal limitations and narrow expectations, of finding the courage to assert one’s self and one’s dignity, of the basic struggle for human freedom—are given great poignancy by the world in which it’s set: Black communities in the rural South in the early 20th century. Zora Neale Hurston, one of the leading figures of the Harlem Renaissance, was intent on depicting the full richness of Black life as it was actually lived, not as dictated by any self-appointed authority, Black or white. She was decades ahead of her time. —John Kenney
The ink had barely dried on the treaties that ended World War II when Norman Mailer published his debut novel, The Naked and the Dead. Based on Mailer’s own wartime experience, it is the story of one Army unit’s invasion of a fictitious Japanese-held island in the South Pacific. The writing is so realistic, so painstakingly detailed, that it reads like a well-written duty officer’s report. The book’s cast is a dozen or so enlisted men and officers of different ethnicities and from different hometowns whose backgrounds Mailer tells in flashback. The flashbacks take on a life of their own and could be the reason there’s always a guy from Brooklyn in every World War II movie ever made. The book became a best seller and made Mailer a celebrity, and he turned his celebrity into something else. He directed bad films, ran unsuccessfully for public office, and picked fights on talk shows. He remained a writer but became a provocateur. This was 1948, postwar America, when the country had instituted the Marshall Plan, a humanitarian effort to rebuild Western Europe. America is not much older today than we were then. But we are certainly different. Difficult to imagine, today, fame visiting a novelist in the way it had Mailer. Just as difficult to imagine that America would willingly rebuild a continent after leading a war effort that saved the world from autocrats. —Kevin McDonnell
Yes, it’s a children’s book, but its poignant genius somehow works its way on you no matter what age you are. Beginning with its arresting first line—“Where’s Papa going with that ax?”—White’s great book about a runt pig, a little girl who befriends him, and a spider that can spell tells a deeply complex story in the simplest way possible. It’s a story about life and death and the difficult pain of growing up, and it unfolds in the most familiar and homespun worlds you can imagine—a livestock barn, a family farm, a county fairground. But what marks it as truly American is its natural fusing of honest, moving sentimentality with a necessary matter-of-factness in the face of life’s great challenges. —John Kenney
The year is 1935, and Harlem is in the middle of the Great Migration—Black families moving from the rural South to the urban North. John Grimes has just turned 14 and feels that his path to becoming a preacher, like his father, is so imminent, so immutable, that he is powerless to follow another. All around him, at home and on the streets of Harlem, the rigidities of the church, the distinctions between the saved and unsaved, and the remission of sin are laid bare for John to grapple with. (A family walking to church in their best Sunday attire doesn’t go unnoticed by the watchful eyes of the “sinners … still wearing their Saturday-night clothes.”) John’s struggle to realize an identity separate from what is expected of him is at the foreground of the book; temptation, rebellion, and desire wait in the wings. American stuff. But also: James Baldwin has said that Go Tell It on the Mountain, his first novel, was the book he had to write if he was going to write anything else. We should be grateful for this book and what followed. —Kevin McDonnell
The thing you’ll hear from those who read On the Road—whether in 1957, when it came out, or right now—is that they didn’t know people could live like that. Jack Kerouac’s book landed like a bomb in the ’50s; it was a story about a guy and his friends who swapped a life of stifling conformity for one of travel and adventure. When I checked out the book from my high school library in the ’90s, the woman behind the desk warned me: “The last person who read this book dropped out of school.” In other words, the text was dangerous. It might alter my life. And it did: I didn’t know people could live like that. In On the Road, Kerouac writes: “The only people for me are the mad ones, the ones who are mad to live, mad to talk, mad to be saved, desirous of everything at the same time, the ones who never yawn or say a commonplace thing, but burn, burn, burn like fabulous yellow roman candles exploding like spiders across the stars and in the middle you see the blue centerlight pop and everybody goes ‘Awww!’ ” After you read this book, you will always be in search of those people, and that life, and the feeling of a life free of conformity. It is a story that only an American could write. —Michael Sebastian
“You want to overturn the existin’ institution, that’s fine. But you got to be sure you know how to build a better one,” says Governor Arthur Fenstemaker, the homespun titan of progressive politics who stands astride Billy Lee Brammer’s first and only novel, a vivid portrait of Texas politics in the 1950s. Fenstemaker, like all the politicians in the book a flawed person, isn’t above wheelin’, dealin’, and playin’ hardball to achieve admirable aims. “The thing to do is work through the institution,” he cackles, “An’ I’m that institution currently…” He is a masterful politician in part because he perceives a truth about his constituents they themselves can’t understand, because it would puncture their self-mythology: “Most of us came into town one Saturday a few years ago and stayed. … We’re urban, by God. All of a sudden the people in the metropolitan areas outnumber the rednecks.” Fenstemaker is a stand-in for one Lyndon B. Johnson, for whom Brammer served as a Senate press aide. And Texas, which fancies itself a frontier, its politicians and people in a state of nature, is a stand-in for America, a nation in which our myths are more real to us than how we actually live. —Kevin Dupzyk
Of the two great movie adaptations that have been made of Charles Portis’s masterpiece, the Coen brothers’ version from 2010 comes closest to capturing the true feel of this remarkable short novel. To properly appreciate the pitch-perfect, peculiar American vernacular of the work, though, you simply have to read the book. Just let the language work its way through you and pretty soon you’ll find yourself talking like Mattie Ross, the narrator of this hard-boiled western and one of the most distinctive, natural, funny, and downright interesting voices in all of American literature. The story of young Mattie’s dogged pursuit of her father’s killer through 1870s Arkansas and the Territory, accompanied by ornery one-eyed U.S. marshal Rooster Cogburn—one of the most memorable figures ever conjured for the page—is a propulsive old-time yarn and a tribute to national character traits we used to lay particular claim to, like loyalty, devotion, relentless tenacity, and sheer bullheaded determination to the utmost extremity. You know, true grit. —John Kenney
Joan Didion is a vexing writer, a bewitching stylist whose greatest spell turns California’s honey-dripping sunshine into a portent of doom but whose mastery of style sometimes overtakes her. Her most famous collections of journalistic essays, Slouching Toward Bethlehem and The White Album, which slice into the fleshiest parts of 1960s and 1970s America, can feel as empty as the Golden State promise. In Play It as It Lays, a short, mean, exquisitely crafted novel about an actress’s psychological breakdown in Los Angeles, Didion directs her considerable gifts at people and plot of her own devising. It is a revelation. Through fiction, she escapes the froideur of her essayistic encounters with real life and authors a takedown of an iconic American era that somehow feels truer than true. —Kevin Dupzyk
Robert Caro’s exhaustive biography of Robert Moses is not just a comprehensive history of 20th-century New York but an instruction manual on how power is acquired and abused in American politics. Despite never being elected to public office, Moses single-handedly changed the face of America’s largest city for forty years. Read on in admiration as a spirited idealist learns how to manipulate power to become a devastatingly effective public servant. Then watch in despair as he consolidates power even more, using it to further his own short-sighted aims at the expense of the city’s poor and minority citizens. It’s a sobering reminder of what can happen in a democracy when no one is paying attention. —Connor Sears
Greil Marcus’s Mystery Train is an account of America’s imagination, mythology, and morality disguised as a book about rock and roll. The book “grows out of records, novels, political writings … there isn’t any separation,” as the author writes in his prologue. Marcus harnesses his vast stores of cultural knowledge and picks six musical acts, each of which gets its own chapter. In the first, Marcus introduces us to a guy named Harmonica Frank, who was born in 1908 and made records in the ’50s for Sam Phillips, the founder of Sun Records. Phillips later signed a guy named Elvis Presley, who is Marcus’s final subject and whose final recording for Sun gives the book its name. In between those chapters, the remaining principals include the Delta blues guitarist Robert Johnson, Bob Dylan’s supporting act the Band, ’70s funk band Sly and the Family Stone, and Randy Newman. The book has remained in print since 1975, and Marcus has been updating chapters and writing new introductions for each new edition. Just so: The original lineup is unimpeachable, but if you buy the book’s thesis, there’ll never stop being encores so long as there’s still an America. —Kevin McDonnell
Macon “Milkman” Dead III, Song of Solomon’s main character, is the grandson of the first Black doctor in his Michigan town, as well as the first Black child born in the town’s hospital. He represents a more well-off section of his community but, despite relative privilege, suffers generational trauma from his family’s history of slavery, displacement, and racial violence. His story is an indelible portrait of the Black experience in America that, in the hands of Toni Morrison, would earn the novel a place on this list all by itself. But the plot of the book, which finds Milkman on an Odyssey-like quest to find gold he believes his family has been hiding for years, picks at another of America’s scabs: our tendency to focus on material wealth at the expense of human ties, even familial ones. I won’t spoil how Milkman’s quest resolves, but I will leave you with an utterance from another character: “I wish I’d a knowed more people. I would have loved ’em all. If I’d a knowed more, I would a loved more.” Song of Solomon came out right after America’s bicentennial; in the late-capitalist shadow of the semiquincentennial, its moral authority is no less needed. —Bellamy Richardson
“How could they live their lives like that with such earnestness,” Tom Wolfe asks, about the people down on Earth, “if they had the faintest idea of what it was like up here in this righteous zone?” That is the question he tries to answer in his account of America’s nascent space program, the Mercury Project, and its inaugural class of astronaut trainees. Seven men, recruited from a field of more than 500 military test pilots, who became so famous they sold their story—before they even had one to tell—to Life magazine for half a million 1959 dollars. Wolfe gets into how NASA had to sell the space program to a bunch of military fighter pilots, who weren’t exactly motivated buyers. NASA, a quasi-civilian outfit, was still a few years out from even having a spacecraft. What’s more, the pilots realized early on that you don’t fly a space capsule; you just sit in it. “Spam in a can,” Wolfe tells us, was their nickname for the burgeoning program. It’s the ambition of it all that gets you—that and the grace notes—in the book, that is—of American meritocracy. A hotshot WWII fighter pilot named Chuck Yeager was breaking speed records and the sound barrier but was unable to qualify for the Mercury Project because he didn’t have a college degree. That didn’t stop Wolfe from giving Yeager his own chapter. It’s probably the best in the book. —Kevin McDonnell
Cormac McCarthy’s cynical 1985 opus, the great anti-western of American literature, follows a kid raised by the horror of mid-19th-century life on the Texas–Mexico border. Blood Meridian’s trademark is inescapable racial violence. Judge Holden, the novel’s hairless, ageless villain, is the sum total of an eternity of colonial excess. (His final chapter is a haunting provocation on war and lust that has left readers wondering, “Just what the hell happened in that outhouse?” for the past 40 years.) It would be almost unbearable, but McCarthy’s terse, poetic prose navigates scalp-hunting gangs, river valleys, and border-town saloons with illuminating ambiguity and brutal honesty. This is how the West was really won. Not by heroes but by men whom you wouldn’t want to spend ten minutes in a room with. —Bryn Gelbart
Forty-one years after its publication, Margaret Atwood’s gripping novel is, unfortunately, only more prescient in its rendering of a dystopian world, set in the United States, where the distinction between church and state has been fully eliminated. The book was inspired by research Atwood—yes, a Canadian—did at Harvard into the first Puritan communities in America and the witch trials that her own ancestor narrowly escaped. One of the book’s more chilling insights is that the strict religious dictatorship that takes over America crushes the free will of all, including those enforcing the laws. As Roe v. Wade is turned back and ICE detainment facilities fill up without due process, the ruthless totalitarian regime in The Handmaid’s Tale feels more realistic than ever. If we all took a long, hard look at Atwood’s writing, perhaps we could gather the moral courage she tried to impart and escape the Puritan impulses we mostly left behind all those years ago. —Sirena He
Deep into the book Lonesome Dove, one of the two main characters, August “Gus” McCrae, offers this observation: “The earth is mostly just a boneyard. But pretty in the sunlight.” It’s an observation only an American could produce. It is simple, direct, and entirely unsentimental. It is also optimistic. Death doesn’t get the last word; beauty does. A line like that could only come from a western, right? But Larry McMurtry’s Pulitzer prize–winning novel is an anti-western. Yes, there are cowboys and Indians, cattle drives and gunfights, but it’s not nostalgic for this world. Lonesome Dove is a lamentation—about what Europeans and their descendants did to the land and what technology and capitalism were doing to them. It’s also a story about friendship and masculinity and ambition and love and all the big themes that only an American author would have the balls to think he could pull off in one book. Oh, and it’s also a damn good adventure story. —Michael Sebastian
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