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If you're bored of reading the same old books over and over, you've landed in the right place. Allow us to inject your reading list with a dose of cool with our list of the coolest books of all time. You could say they're the type of books that should come with a pair of sunglasses.
UPDATE: Ready for another injection of cool? We've added a couple of more recent reads to our list, ones that became part of the cultural zeitgeist in the years in which they were released. These are Sally Rooney's Conversations with Friends and cult fave My Year of Rest and Relaxation by Ottessa Moshfegh.
Films you can quote for cheap giggles down the pub; records (vinyl, natch) earn you kudos among a select coterie of like-minded obsessives; but nothing – absolutely nothing – says understated cool (always the coolest cool) like a well-thumbed copy of A Confederacy of Dunces.
Of course, the definition of "cool" is different for everyone. But we're thinking unexpected adventures, irreverent writing, stories that go against the grain and characters that refuse to play by the book. Want in on the action? Get yourself down to your local bookstore immediately and get acquainted with our selection of more than 52 books that fit the bill. Gallons of cool guaranteed.
The coolest books of all time
at AmazonThe imagery and language of Orwell’s Nineteen Eighty-Four permeated society in the 20th century and continues to do so in the 21st. Perhaps the most visionary novel ever written, it foretold a world of surveillance and totalitarian regime. Big Brother, thoughtcrime, Room 101, newspeak and doublespeak; all chilling portents which become more valid by the day.Image Credit: Secker & Warburg
at AmazonKurt Vonnegut’s bizarre fantasy satire has been banned many times in the US since 1969, which is always a good sign. A prisoner of war is saved from the bombing of Dresden when he and others are imprisoned in a slaughterhouse beneath the city. There, he retreats into a post-modern hyper-reality where he is abducted by extra-terrestrials. Stick with us, this is pivotal.Image Credit: Vintage
at AmazonWhen the name of your book enters the common lexicon, you know that you’ve hit on something. Heller’s classic ‘no-win’ situation finds Captain John Joseph Yossarian battling the circular logic of wartime bureaucracy in order to stay alive, or at least die trying. As a text is has become vastly influential, though it polarized critics on its release.Image Credit: Vintage
at AmazonKesey was a hugely influential character in US counter-culture, linking the beat movement of the 50s with the hippies of the 60s. His devastating novel One Flew Over the Cuckoo’s Nest was born of his experiences working on CIA-funded drug trials, and spawned the Oscar-winning film. The book is narrated by Chief Bromden and is fiercely critical of the treatment of mental illness.Image Credit: Penguin
at AmazonOne of the most influential dystopian novels of all time, A Clockwork Orange used its own secret language to punctuate its jarring narrative, a bastardisation of English and Russian. Its protagonist Alex is a terrifying societal construction; an intelligent and sophisticated sociopath who revels in chaos and violence. His brutality is later mirrored by his treatment at the hands of the state. Stunning.Image Credit: Penguin
at AmazonAnother example of a classic cult novel, Toole would only receive his dues after his death (which came at tragically untimely 31, when he took his own life). He won the Pulitzer Prize for Fiction posthumously, and A Confederacy of Dunces, about the adventures of a slovenly, eccentric, latter day Don Quixote in 60s New Orleans is loved by a legion of fans.Image Credit: Penguin Classics
at AmazonThe archetypal ‘great American novel’, Gatsby, like so many works of literary genius, went underappreciated while Fitzgerald was alive. Only after his death did its resonance become deafening. The decline of the American Dream and a withering social commentary of moral decline and social decay typify this defining moment in literary history.Image Credit: Digital Reads
at AmazonConsistently cited as one of the most influential graphic novels ever written, Alan Moore and Dave Gibbons’ ground-breaking story of an alternate USA in which it won the Vietnam war and welcomed (and later shunned) a generation of masked vigilantes resonates as much today as it did in 1986. As, indeed, does the recurring anti-Reaganist mantra ‘who watches the watchmen?’. Comic fan or not, everyone needs to own this.Image Credit: DC Comics
at AmazonIf there’s a cooler writer than Hemingway, we’ll eat our hats. And coats. His first novel finds American journalist Jake Barnes and a group of hard-drinking cohorts travelling from Paris to Pamplona to immerse themselves in bullfighting. Less a love triangle than a love pentagon emerges with the sexually unrepressed Lady Brett Ashley, causing smouldering tension in the Basque country.Image Credit: Penguin
at AmazonLudicrously ahead of its time, Gibson’s cyberpunk archetype immersed itself in computer networks and hacking, crossing over from the realm of the hardcore geek into the mainstream as a slow-burning cult classic. Anti-hero Case and augmented ‘razorgirl’ Molly enter a shadowy world at the behest of ex-military officer Armitage. Brain-melting.Image Credit: Gateway
at AmazonWithout question the crowning achievement of Truman Capote’s career, his coverage in non-fiction novel form of the 1959 murder of a devout farmer, his wife and two of their daughters in Holcomb, Kansas, is utterly, page-turningly gripping. Capote took six years to write it, befriending murderer Perry Smith while he awaited execution.Image Credit: Vintage
at AmazonChaotic, psychedelic, and dripping in hallucinogens, this is Thompson’s crowning work of gonzo madness. Centring around the exploits of journalist Raoul Duke and his attorney Dr Gonzo, things rapidly degenerate (including the integrity of the narrative) as the pair ditch their assignment to cover a motorbike race and lose themselves in a haze of acid, ether, cocaine and mescaline in Sin City.Image Credit: Harper
at AmazonFiercely masculine and fiercely anti-corporate, Chuck Palahniuk’s Fight Club is that rare novel that only emerges a handful of times in a generation. The nameless narrator shifts from being a sleeping consumer to becoming embroiled in the creation of an underground fighting club with the charismatic Tyler Durden. The clubs expand into cells across the nation, becoming radical. Couldn’t be more cool, basically.Image Credit: Vintage
at AmazonThanks to the cinematic adaptations of his books, No Country for Old Men and The Road, Cormac McCarthy’s stock has never been higher. However, in the literary world, it’s his 1985 novel, Blood Meridian that is widely acknowledged as his masterpiece. Set in the Wild West and following the adventures of The Kid, Blood Meridian is a shocking, uncomfortable and unforgettable work of genius.Image Credit: Picador
at AmazonFew writers manage to say so much about what appears to be so little as acclaimed Japanese author Haruki Murakami. Norwegian Wood might be his best known work, but The Wind-Up Bird Chronicle is arguably his best. A typically mesmeric story, it focusses on the supposedly ordinary life of Toru Okada. In expertly drawing Okada in a bewildering variety of colours, Murakami succeeds in saying much about the confusion of late 20th century life.Image Credit: Vintage
at AmazonProbably the most well-thumbed text in the Beat writers’ canon, Kerouac’s On The Road has been credited with much influence in creating the counter-culture that would blossom in the 60s and 70s. Written in spontaneous prose, it is the ultimate literary road trip, a patchwork of Americana, jazz, booze and drugs.Image Credit: Penguin
at AmazonA contemporary of Brett Easton Ellis, Donna Tartt’s The Secret History is a murder mystery presented in reverse, a modern Greek tragedy involving a group of students studying classics at an upscale Vermont college who stage a wild ‘bacchanal’ which ends in the death of a local farmer. The murder soon exposes the fault lines in the tight-knit group’s relationship.Image Credit: Little, Brown Book Group
at Amazon“I'm into, oh murders and executions mostly. It depends,” says Patrick Bateman, the psychotic investment banker at the dark heart of American Psycho. People presume he means mergers and acquisitions, but as the bodies stack up, it appears otherwise. A cartoonish, sickeningly violent allegory of capitalism and consumption taken to its logical conclusion, it is one of the 20th century’s most vivid and controversial novels.Image Credit: Picador
at AmazonWolfe’s damning social and moral critique originally ran as a serial in Rolling Stone, before Wolfe revised it and released it as a novel. Working on the premise that your life can spiral out of control no matter how much money or influence you have, it finds millionaire trader Sherman McCoy unable to control events after a hit and run incident in the Bronx. Ignore the film, it’s awful.Image Credit: Vintage
at AmazonPerfume is a book that is unique in its inception and intoxicating in execution. It follows the life of the wretched Grenouille in 18th century France, an abandoned child with an astonishing acute sense of smell. In search of the perfect scent, he becomes a prolific and talented murderer, while studying the ancient art of making perfume. A book unlike any other.Image Credit: Penguin
at AmazonJeffrey Eugenides may have only written three books, but two of those are The Virgin Suicides (big tick) and this, Middlesex (even bigger tick). An unapologetic, purposefully constructed epic family saga, Middlesex not only examines the trials and tribulations of three generations of Greek Americans, but places that within the context of America’s intersex community. Comprehensively researched, empathetic and drenched in a heady grandeur, Middlesex richly deserved its Pulitzer Prize.Image Credit: Fourth Estate
at AmazonBurroughs didn’t so much disregard the literary rule book with Naked Lunch - he tore it to shreds and reassembled it as he saw fit, making his book one of the first examples of postmodern literature. Soaked in drug use, junkie William Lee (an alter ego for Burroughs himself) chases his next fix, warping from reality on the road between the US and Mexico into the Interzone, a dreamlike place based on Tangiers. Insanity in print.Image Credit: Penguin
at AmazonGrasping hold of the zeitgeist, author Douglas Coupland wrote about his own experience, about the disaffected generation that picked up after the baby boom. Though the phrase had been coined as early as the 50s, Coupland popularized it, along with others such as the ‘McJob’. It was biting, and full of pop culture, aligning him with the likes of Chuck Palahniuk and Irvine Welsh.Image Credit: Abacus
at AmazonMind-bending and thoroughly post-modern, Calvino’s masterpiece of self-reference (‘you’ are part of the plot), its dizzyingly clever, labyrinthine construction has made it a classic. If there was ever a novel to make you look like an urbane Poindexter on the train/bus, then this is it.Image Credit: Vintage
at AmazonVastly disturbing, Banks’ first novel caused a storm of controversy for the blank violence emitting from its troubled protagonist Frank Cauldhame, who describes a childhood growing up on the rugged north east coast of Scotland. The impending arrival of Frank’s brother Eric, who has escaped from an asylum, coupled with Franks bursts of mindless anger, create an unsettling gothic horror.Image Credit: Abacus
at AmazonThe ‘laureate of American lowlife’, in Factotum Bukowski presented his alter-ego Henry Chinaksi, a shambling booze-hound meandering from one disastrous menial job to the next with an increasing level of disdain as he struggles to get himself published as a writer. Set in the seamy world of the 40s LA barfly, this is a grubby classic.Image Credit: Virgin Books
at AmazonPenned in the breathlessly inventive style that made On The Road so alluring, The Dharma Bums is a superior novel to its more illustrious older sibling. Recounting Kerouac’s dichotomic lifestyle – between the booze-sodden life of the neon urban sprawl and his contemplative, Buddhist influenced days spent in the idyllic outdoors – in a typically evocative manner, the book remains a countercultural bible.
at AmazonWith A Heartbreaking Work of Staggering Genius, Dave Eggers scored himself a place as a finalist for a Pulitzer, as well as topping many a ‘book of the year’ list. A fictionalised memoir about having to raise his eight-year-old brother as a 20-year-old following the deaths of both their parents, it was much as its title suggested.Image Credit: Picador
at AmazonAnother stunner from Chuck Palahniuk, this bleak but blackly humourous horror is more psychological in tone, rather than the viscerally explicit style that he also turns his hand to. Taking the form of a coma diary, written while protagonist Misty’s husband is in a coma following a suicide attempt, it’s a peculiar and deeply unsettling fable of small town conspiracy.Image Credit: Vintage Digital
at AmazonOK, if you want to be pedantic, Howl isn’t really a book, it’s a poem. However, in terms of provocative prose and scandalous storytelling, Howl can’t be bettered. From its oft-quoted opening line (‘I saw the best minds of my generation destroyed by madness’) to its portrayal of radical jazz loving, drug-taking, homosexual communists running counter to the vows of the American Dream, Howl has long been a key beat generation text.Image Credit: Penguin Classics
at AmazonThe awards that Franzen’s third novel The Corrections didn’t win, weren’t really worth winning. Even some of the ones it did win weren’t worth winning, an endorsement from the Oprah Winfrey book club, for example, which he dissed and resulted in a petulant shunning of him by the media mogul. Whatever, this story of family dysfunction is a modern masterpiece.Image Credit: Harper Perennial
at AmazonBallard’s disturbing Crash orbits a peculiar, disparate group of car-crash survivors and fetishists who find themselves aroused by the violent meeting of man and machine. Enormously controversial, it dissected consumer culture and obsession with celebrity over a backdrop of explicit sexual and mechanical imagery.Image Credit: Fourth Estate
at AmazonOnce Ellroy’s scattershot, ‘telegraphic’ prose style sinks into your consciousness, it’s stuck there. The natural successor to Hammett and Chandler, the legends of the hard-boiled style, Ellroy’s American Tabloid, the first in his Underworld trilogy, is a tangled web, intertwining the assassination of JFK with the CIA, the mob and the FBI in his own inimitably stark style. Super cool.Image Credit: Cornerstone Digital
at AmazonTrying to summarise Pynchon’s transgressive, post-WWII masterpiece is possibly pointless. It’s labyrinthine and features 400 characters. Still, it is regarded as one of the greatest examples of post-modern literature in the English language, and one of the great American novels. It’s a confusing, self-referential mash of signs and symbols, as a quest to uncover the secrets behind ‘the black device’, a piece of mysterious military hardware, is revealed.Image Credit: Vintage Classics
at AmazonBizarre, brilliant, and for Pynchon, brief, The Crying of Lot 49 concerns his heroine Oedipa Maas and her quest to uncover a conspiracy surrounding a shadowy alternative postal service working on the US underground. Though only short, Pynchon weaves multi-threaded plot in what might be a parody of post-modernism, despite being a notable example of the genre.Image Credit: Penguin Press
at AmazonA clear indicator of a novel permeating, and in some cases transforming, everyday life is in the adoption of the book’s language. Erica Jong achieved this in spades with her remarkable debut novel. An intelligent, captivating, vivid and not to mention highly contentious account of a woman’s desires, it has become a key feminist tract since its publication. The origin of the phrase ‘zipless f**k’ can be traced back to this fascinating novel.Image Credit: Open Road Media
at AmazonCharles Burns released his 12-issue comic book series Black Hole over a decade from 1995, a bleak but brilliant tale of suburban alienation when teenagers who contract a mysterious sexually transmitted disease start to develop bizarre physical mutations, all drawn in eerie black and white, evoking the feel of classic teen horror films.Image Credit: Jonathan Cape
at AmazonControversy and cool fit each other like hand and glove. The greater the controversy, the greater the cool. So it goes without saying that Hubert Selby Jr’s notorious debut novel has acquired something of a hip rep. Depicting a rundown area of New York in the 1950s, Last Exit to Brooklyn features drug addicts, wanton violence, rape, crime and any other deviancy you care to mention. Penned in everyman, spontaneous prose, it’s the book most aspiring writers hope to emulate.Image Credit: Penguin Classics
at AmazonWhen Movern Callar wakes up to find her boyfriend dead in the kitchen, having taken his own life, she decides to steal and sell his unpublished novel, passing it off as her own work. Warner won the prestigious Somerset Maugham prize for his debut novel, and it was also made into a film by Lynne Ramsay.Image Credit: Vintage Classics
at AmazonThis 2018 hit is based around an unusual high concept idea. A rich young woman aims to sleep for an entire year, to get away from the world. It's a biting and funny novel about privilege and how people can, or should, approach life. You probably aren't going to fall in love with the narrator in this one, but that is by design. Not all characters have to be good and kind, folks.
at AmazonNormal People put Sally Rooney on the map for many, but her previous novel Conversations with Friends has a certain cool factor the more popular book arguably lacks. It's a story of repressed young people, and the communications of silence, and when was is said is not really what is meant. Much of the book is told through phone chats, giving it a modern of-its-time flavour,
at AmazonIt was Amis’s experiences working on the screenplay for derided (and largely unwatched) sci-fi film Saturn 3 which lead him to write Money. As such, this is a scathing takedown of celebrity culture, his protagonist a deeply sleazy, hard-drinking ad director who heads to New York to make his first film, the first step on a path to his destruction.Image Credit: Vintage Digital
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Content Director
As Content Director of Shortlist, Marc likes nothing more than to compile endless lists of an evening by candlelight. He started out life as a movie writer for numerous (now defunct) magazines and soon found himself online - editing a gaggle of gadget sites, including TechRadar, Digital Camera World and Tom's Guide UK. At Shortlist you'll find him mostly writing about movies and tech, so no change there then.
