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The coolest books of all time: amazing novels to read

Away with thee, Harry Potter.

The coolest books of all time: amazing novels to read
Marc Chacksfield
06 April 2022

Welcome to our list of the coolest books of all time - the type of book that should come with a pair of sunglasses.

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.

Want in on the action? Get yourself down to your local bookstore immediately and get acquainted with the following 50 tomes. Gallons of cool guaranteed.

The coolest books of all time

The coolest books of all time

1. Slaughterhouse Five – Kurt Vonnegut (1969)

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Kurt 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.

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2. Nineteen Eighty-Four– George Orwell (1949)

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The 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.

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3. Catch 22 – Joseph Heller (1961)

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When 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.

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4. One Flew Over The Cuckoo’s Nest – Ken Kesey (1962)

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Kesey 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.

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5. Alan Moore – Watchmen (1986)

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Consistently 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.

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6. A Clockwork Orange – Anthony Burgess (1962)

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One 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.

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7. The Great Gatsby – F. Scott Fitzgerald (1925)

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The 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.

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8. The Sun Also Rises – Ernest Hemingway (1926)

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If 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.

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9. A Confederacy Of Dunces – John Kennedy Toole (1980)

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Another 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.

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10. Fear And Loathing In Las Vegas – Hunter S Thompson (1971)

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Chaotic, 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.

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11. Blood Meridian – Cormac McCarthy (1985)

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Thanks 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.

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12. The Wind-Up Bird Chronicle – Haruki Murakami (1997)

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Few 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.

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13. Bonfire Of The Vanities – Tom Wolfe (1987)

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Wolfe’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.

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14. Neuromancer – William Gibson (1984)

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Ludicrously 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.

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15. In Cold Blood – Truman Capote (1966)

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Without 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.

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16. George Eliot - Middlemarch

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Yeah, forget what you remember about Middlemarch. This is a book that is packed with laser-sharp thoughts about society and human nature. With timeless prose and brutal barbs, this is one of the best and timeless looks at what makes all of us tick.

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17. Fight Club – Chuck Palahniuk (1996)

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Fiercely 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.

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18. American Psycho – Bret Easton Ellis (1991)

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“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.

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19. On The Road – Jack Kerouac (1951)

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Probably 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.

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20. Trainspotting – Irvine Welsh (1993)

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Irvine Welsh’s stunning debut novel, written in phonetic Scottish slang, defined a generation. Where Danny Boyle’s iconic film portrayed Mark Renton as a likable if flawed heroin addict, the book is less generous with him as the morally dubious focal point of a group of friends, enemies and psychopaths hopelessly tethered to opiates in dilapidated 80s Edinburgh.

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21. The Secret History – Donna Tartt (1992)

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A 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.

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22. Middlesex – Jeffrey Eugenides (2002)

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Jeffrey 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.

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23. Perfume – Patrick Suskind (1985)

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Perfume 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.

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24. To The Lighthouse - Virginia Woolf

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This is a novel of such stunning prose that it demands to be read by all. Set in Scotland, it's about people's lives that mirror the erratic nature of the sea. It's the type of novel that sweeps you away with its words and themes and makes you think about why we all exist, all crafted in the most beautiful of ways.

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25. Gravity’s Rainbow – Thomas Pynchon (1973)

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Trying 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.

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26. If On A Winter’s Night A Traveller – Italo Calvino (1979)

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Mind-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.

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27. Song Of Solomon - Toni Morrison

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Apparently this is Barack Obama's favourite book which instantly adds a layer of cool. But beyond this recommendation, this is a novel about Macon "Milkman" Dead and the characters that live a live with him. It's brutal in places but this is a stunning novel that's steeped in black history.

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28. Naked Lunch – William Burroughs (1959)

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Burroughs 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.

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29. Everything Is Illuminated – Jonathan Safran Foer (2002)

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A young American Jew travels to the Ukraine to try and find the woman who saved his grandfather’s life during the Nazi occupation. Bizarre, funny and touching, it marked its author Jonathan Safran Foer out as a smouldering talent.

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30. Strangers On A Train - Patricia Highsmith

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Hitchcock may have made the novel famous but head back to Patricia Highsmith's prose and you are gifted with one of the tensest novels of all time. Seriously, this novel has more grip than your average carpet fitter. It's also a brilliant character study of flawed people looking to make something of themselves, all in the name of murder.

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31. Generation X – Douglas Coupland (1991)

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Grasping 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.

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32. The Wasp Factory – Iain Banks (1984)

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Vastly 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.

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33. Howl – Allen Ginsberg (1955)

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OK, 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.

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34. The Dharma Bums – Jack Kerouac (1958)

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Penned 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.

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35. Fear Of Flying – Erica Jong (1973)

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A 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.

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36. Black Hole – Charles Burns (1995)

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Charles 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.

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37. Last Exit To Brooklyn – Hubert Selby Jr (1964)

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Controversy 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.

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38. The Dice Man – Luke Rhinehart (1971)

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A psychiatrist called Luke Rhinehart (the novel was written under the pen name by George Cockcroft) begins making his life decisions on the roll of a dice, entering a subversive world of sex and violence. Banned variously, The Dice Man is pretty much the definition of a cult novel, have a wildly fanatical fan base, and having influenced hundreds books and movies ever since.

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39. The Crying Of Lot 49 – Thomas Pynchon (1966)

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Bizarre, 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.

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40. A Heartbreaking Work Of Staggering Genius – Dave Eggers

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With 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.

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41. Morvern Callar – Alan Warner (1995)

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When 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.

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42. Diary – Chuck Palahniuk (2003)

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Another 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.

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43. Crash – JG Ballard (1973)

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Ballard’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.

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44. The Corrections – Jonathan Franzen (2001)

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The 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.

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45. Underworld - Don DeLillo (1997)

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Don DeLillo secured his place as one of the greatest American novelists with Underworld, having already influenced the likes of Brett Easton Ellis and Jonathan Franzen. He also aligned himself with other titans of the US literary world like Cormac McCarthy, Philip Roth and Thomas Pynchon with his postmodern tome chronicling the life of a cuckolded waste management executive in New York.

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46. Factotum – Charles Bukowski (1975)

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The ‘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.

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47. Money – Martin Amis (1984)

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It 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.

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48. Ghost World – Daniel Clowes (1993)

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Celebrated author and cartoonist Daniel Clowes constructed an immersive narrative in his Ghost World comics, which were brought together as a single volume in 1997. Enid and Rebecca are best friends, searingly witty consumers and critics of pop culture, living in a nameless suburbia. Both are classic outsiders, nerdy but also effortlessly cool. A blueprint for hipster culture.

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49. American Tabloid – James Ellroy (1995)

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Once 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.

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50. Fun Home - Alison Bechdel

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This fantastic graphic novel, from the author who created the Bechdel Test, is a fantastic looks at someone's childhood through diary entries and literary nods. The book beautifully plays out Bechdel's relationship with her father, his eventual death and her coming out to her family.

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