Image: Ryan MacEachern/Penguin

Image: Ryan MacEachern/Penguin

If the Fifties were in black and white, the Sixties burst into colour – one of the most tumultuous, subversive and revolutionary decades of the 20th century. It was the decade of the pill, Black Power, the Stonewall riots, Vietnam, and Flower Power. It was the decade The Beatles got bigger than Jesus.

It was also the decade that launched second wave feminism, and the decade “pro-choice” found a voice. It was the decade that the “Silent Generation” gave way to the “Baby Boomer Generation” who unleashed a tidal wave of rebellion, self-confidence, and experimentation. It was a decade defined by a spate of major political assassinations, mass protests and (sometimes) bloody riots.

All of which is to say, the Sixties were a momentous, fascinating decade of massive social change. And, as usual, there was no shortage of writers with their typewriters at the ready, on hand to record it all. Or, in some cases, to change the world themselves.

Here – from Betty Friedan to Malcolm X, Anthony Burgess to Roald Dahl – are twenty books that helped shape the 1960s.

The L-Shaped Room by Lynne Reid Banks (1960)

Jane is a 27-year-old middle-class woman, pregnant and unmarried, and kicked out of her father's home to face her shame alone. So she does what most women in early 1960s Britain in her predicament had to do: hole up in a bug-infested boarding house in Fulham to live off tinned spaghetti and hide from the narrow-minded world outside.

There, within those tobacco-yellow walls she meets a kaleidoscope of other social outcasts: immigrants, a jazz musician, prostitutes and others. Through them, she finds friendship and love, and – ultimately – carves out a happiness that she can own.

Published seven years before abortion was made legal and a year before the pill first arrived in Britain, this was a pre-Beatles London yet to get groovy. It captured a moment still caught in the past, where landlords could hang signs saying “no blacks, no Irish” and women could be sacked for falling pregnant. But this open-hearted novel was among a handful of women-focused texts that explored sex-for-pleasure, the complexities of abortion, race, class and female choice.

To Kill a Mockingbird by Harper Lee (1960)

From the moment To Kill A Mockingbird hit the shelves in 1960 it captured the hearts of millions of readers across the world, thanks to its portrayal of a white lawyer defending a Black man accused of rape in 1930s Mississippi.

It has since become one of those rare novels that transcends its own form, more a cultural artefact than a book – a paean to the importance of standing up for truth and justice, and being innocent until proven guilty.

As the historian, Joseph Crespino put it, "In the twentieth century, To Kill a Mockingbird is probably the most widely read book dealing with race in America, and its main character, Atticus Finch, the most enduring fictional image of racial heroism."

Published at a time when the Civil Rights movement was about to gain momentum, To Kill A Mockingbird held up a mirror to a society on the brink of radical social change, reminding the nation that tolerance is essential, and that just because a prejudice is de rigeur, that does not mean it is right.

Lady Chatterley's Lover by D.H. Lawrence (1960)

Something of a rogue entry, this, as it was originally published in 1929 in Paris. But back then, tastemakers of the British establishment considered the story so obscene that they thought genteel society couldn't possibly have the stomach for so much smut.

It would take 31 years for the collective stiff-upper lip to soften. At least, that's what Penguin thought when it made its move. The result was a sensational obscenity trial that rattled Britain by the bed boards. After a six-day trial, the Old Bailey jury found the book – about the illicit affair between a high-class lady and her gamekeeper – not to be obscene. Penguin was acquitted, and the book sold 200,000 copies on the first day in a watershed moment that remapped Britain's cultural landscape.

Lady Chatterley's publication not only meant sex was no longer a taboo in art and entertainment, but paved the way for a new approach to human rights, from the legalisation of homosexuality to the abolition of the death penalty, rules on abortion and divorce reform.

It marked, as Geoffrey Robertson QC wrote in 2010, “the first symbolic moral battle between the humanitarian force of English liberalism and the dead hand of those described by George Orwell as 'the striped-trousered ones who rule'.”

Tropic of Cancer by Henry Miller (1961)

You can't mention Lady Chatterley's Lover without a nod to Tropic of Cancer, Henry Miller's novel about a lone writer hunting for sex in Paris' seedy underworld.

He began work on it shortly after arriving in bohemian Paris in 1930, then a haven for lost writers in search of a soul. “I start tomorrow on the Paris book,” he wrote to a friend. “First person, uncensored, formless – fuck everything!”

Well, if not everything, he certainly did the status quo. Published by a French soft-porn concern, Tropic of Cancer came wrapped in a warning: "Must not be taken into Great Britain or USA". It would not see the light of day in either country for a generation.

Finally, a year after the Lady Chatterley's Lover trial, Grove, the publisher, won its own landmark legal case that overturned its American ban. It became an instant best seller, and turned Miller into, as Jeanette Winterson wrote, “the priapic prophet of sexual freedom”.

Until, that is, second-wave feminism emerged, and both he and Lawrence went from being darlings of the Sexual Revolution to personae non gratis – called out by critics like Kate Millett and Germaine Greer for their misogyny and “counter-revolutionary” maintenance of the patriarchy.

A House for Mr Biswas by V. S. Naipaul (1961)

A lot happens in this rumbling epic about a Hindu Trinidadian man who climbs out of the well of poverty in a bid to secure himself a house.

Starting with Biswas' birth and ending with his death, the novel examines a life lived in poverty and what it takes to get out – a slipshod education, his reluctant marriage into an awful family, professional failures, battles with depression, the constant fights with his snobbish in-laws and the lucky breaks that lead him towards happiness.

It is, as the novelist Teju Cole wrote, a book that rails against “sad obscurity, against surrender, against darkness... a book for knowledge, for determination, for ragged unyielding life, a book that, over its great and complex length, shelters the one who reads it.”

The book's arrival collided with that of tens of thousands of migrants from the Caribbean islands in Britain to help rebuild the nation and staff the NHS. Racism was rife. But this A House for Mr Biswas – a primary factor in Naipaul's 2001 Nobel Prize citation – offered British readers a window into Caribbean life, its culture and people that few had seen before (though it is worth noting that Naipaul's views on race and colonialism have not been without controversy).

The Prime of Miss Jean Brodie by Muriel Spark (1961)

Muriel Spark’s school teacher may have existed on the page in the 1930s, but it was the Sixties that she captivated. Miss Jean Brodie first appeared in a story for The New Yorker before being published as a novel in 1961.

The sparky, irreverent and hopelessly shy romantic (the “Miss” is important) was adored by the decade, become a pop culture phenomenon and inspiring a stage version with Sixties queen Vanessa Redgrave on both the West End and then Broadway (Zoe Caldwell took on Redgrave’s role, earning a Tony in the process).

Then, three years later, Maggie Smith took on Brodie on the big screen.

The Golden Notebook by Doris Lessing (1962)

Doris Lessing denied that The Golden Notebook was a “trumpet for women’s liberation” or an account of “the sex war” of the 1960s. But that's exactly how women at the time read it.

Either way, this daring exploration of communism, women's lib, the female orgasm, motherhood, menstruation, and mental health was hailed as the “feminist Bible”. 

It tells the story of Anna, a novelist and mother, in the midst of a mental breakdown. "It's all due to the times we live in," a doctor tells her. So she keeps four notebooks – black, red, yellow and blue – through which she divides and explores her various identities in a bid to make sense of her life and the world.

Its candour shattered taboos like crockery in an earthquake. “I remember vividly the state of excitement, terror and awe in which I read it,” wrote the novelist Margaret Drabble of the first time she read it. “Here was a writer who said the unsayable, thought the unthinkable, and fearlessly put it down there, in all its raw emotional and intellectual chaos.”

A Clockwork Orange by Anthony Burgess (1962)

“The trombones crunched redgold under my bed, and behind my gulliver the trumpets three-wise silverflamed, and there by the door the timps rolling through my guts and out again crunched like candy thunder. Oh, it was wonder of wonders.”

In 1962, as it is today, Burgess' vocabulary – a woozy cocktail of Russian, Romani and rhyming slang – was truly the wonder of wonders (the above, by the way, is Anthony Burgess' narrator describing Beethoven from his bedroom).

Set in a near-future society overrun by a culture of youth violence, it tells the story of Alex, the classical-music mad leader of a feral gang called “the droogs”, who go on a spree of robbery, rape and "ultra-violence". Inevitably, it lands Aex in jail where he undergoes a bout of terrifying, mind-altering aversion therapy meted out by the authorities.

Written on the cusp of a youthquake that would change the western world, conservative Britain was gripped by fears of juvenile delinquency. A Clockwork Orange both reflected those fears, and made fun of them.

The novel remains one of the most original, controversial and successful books of the last century, a novel so singularly inventive that, once read, it can never be forgotten.

The Feminine Mystique by Betty Friedan (1963)

By the dawn of the 1960s, America was still hair-net deep in the post-war cult of the housewife: a woman's life was to be lived indoors, preferably in the kitchen with the odd sojourn to the bedroom – when her husband saw fit.

To Betty Friedan, this was tantamount to genocide. "The women [...] who grow up wanting to be 'just a housewife',” she railed in one of the more sensational passages, “are in as much danger as the millions who walked to their own deaths in the concentration camps..."

And for that, she blamed advertising, women's magazines, and the educational system for a problem that “has no name” – a misery pandemic that was “burying millions of American women alive”. So she gave it a name: The Feminine Mystique.

The book became a battle cry for young women all over the western world. Or, as concluded her 2006 obituary in the New York Times, it “ignited the contemporary American women's movement in 1963, permanently transforming the social fabric of the United States and countries around the world.”

It sold millions of copies and made Friedan world famous, sparking the fuse for second wave feminism.

The Bell Jar by Sylvia Plath (1963)

Sylvia Plath’s semi-autobiographical novel may have been set a decade before it was published, but it deals with the increasing conversation around women’s mental health - or lack thereof - and the societal roles they were expected to take.

The Bell Jar earned a famous legacy swiftly - Plath (who originally published the novel under the pseudonym Victoria Lucas) died by suicide just a month after its publication and the novel didn’t receive a US release until 1971.

But it remains a novel of oft-revisited literary worth, not least for the vacuum-like way women were expected to behave in the mid-century.

Charlie and the Chocolate Factory by Roald Dahl (1964)

Find a child, anywhere on earth, who wouldn't give up their Xbox for a day in a sweet factory where you can boat down chocolate rivers, eat an entire meal in a single stick of chewing gum, or guzzle a drink so fizzy they make you fly.

Roald Dahl's Charlie and the Chocolate Factory – about a boy who does all that and more – was the stuff of dreams. It whizzed off the shelves, selling 10,000 copies in the first week, and was hailed by the New York Times as "fertile in invention, rich in humour, acutely observant … he lets his imagination rip in fairyland".

His anarchic spirit, brio and sherbert-sharp wit showed a new way of educating children, by entertaining them at the same time. He didn't patronise them, but spoke to them as people.

As he told an interviewer, "a good children's book teaches the uses of words, the joy of playing with language. Above all it helps children learn not to be frightened of books … If my books can help children become readers, then I feel I have accomplished something important." He certainly did that.

The Millstone by Margaret Drabble (1965)

This is a love story, really, but not between lovers – between a mother and her daughter, swept up in the torrent of stigma surrounding single motherhood of the time. Back then, to be an unmarried mother was worse than being a bad mother in wedlock. It was considered a sin.

The Sixties, by 1965, were in full swing. But not for women like Rosamund, our narrator. She's a buttoned-up middle-class virgin who knows nothing about sex. Then, after a one-night stand with a BBC newsreader she thinks is gay, she falls pregnant (one of “life's little ironies”).

She never tells him, and resolves to have the baby come what may. What fellows is a paean to maternity, and the unbreakable bond between mother and child, as Rosamund navigates the realities of being pregnant in 1960s England: the pain over whether to illegally self-abort, her journey through the fledgling NHS, or the stigma of inflicting “the slur of illegitimacy” on a child.

The book was an instant bestseller, as Rosamund became an icon for a new kind of woman – the kind who could have a career and a baby, and be just fine in a world that tells her she can't.

A Single Man by Christopher Isherwood (1965)

Published four years before the Stonewall riots ushered in the modern gay civil rights era, Christopher Isherwood's masterwork about a man struggling to come to terms with the death of his partner was sensationally ahead of its time.

The story follows George, a middle-aged English university lecturer living in California, across a single day of his life, not long after Jim was killed in a car crash. He's a courageously likeable figure. But he's also angry. And not just at his loss, but at suburban society that condemned his love.

“People with freckles aren’t thought of as a minority by the nonfreckled,” George tells his class. “They aren’t a minority in the sense we’re talking about. And why aren’t they? Because a minority is only thought of as a minority when it constitutes some kind of a threat to the majority, real or imaginary.”

It jittered the establishment, at a time when gay men in a number of US states could still be castrated for having sex in their homes. For Isherwood, homosexuality was now political. And A Single Man – one of the all-time classics of gay literature – addressed head on the right for homosexuals to recognised as a minority.

The Autobiography of Malcolm X by Malcolm X and Alex Haley (1965)

On 21 February 1965, Malcolm X – “the angriest black man in America”, in his own words – stepped out at the Audubon Ballroom in New York City to address 400 people. Before he opened his mouth, a man from the Nation of Islam leapt from the crowd and shot him in the chest with a sawn-off shotgun. Two more men then emerged and opened fire. By 3.30pm he was dead.

It became one of the most famous assassinations of the 1960s (in a crowded field), ending the life of one of the loudest voices of America's civil rights movement. But, if there was one silver lining to the brutal tragedy, it was that he had just finished his autobiography alongside the journalist Alex Haley. People would at least know his story, in his own words.

Published just a few moths later, few books on the Black American experience rang out louder than this. If any. It tells the story of his life – from gun-slinging thief to jailbird to his conversion to the Nation of Islam (with whom he fatefully fell out) to firebrand-in-chief of the civil rights movement.

It was a story that would make him a martyr for the cause of racial equality, and an ideological hero not just for America's Black youth, but for any young person who demonstrated for equality in the late 1960s.

Herzog by Saul Bellow (1965)

Here was a story about a middle-aged Jewish man in the throes of a mid-life crisis. He's 48 and emerging from a bitter divorce (his second). He has a child by each of his ex wives, and his career as a writer and academic is beached. So he begins fanatically writing letters - “ to the newspapers, to people in public, to friends and relatives and at last to the dead, his own obscure dead, and finally the famous dead."

The book sold 142,000 copies and remained on best-seller lists for forty-two weeks. Bursting with jokes, thought-watering riffs and scorching comments on the state of the “modern condition”, it cemented Bellow as one of the greatest prose stylists of the 20th century. It was a reputation he cashed in with a Nobel Prize in 1976.

In the words of the Nobel Committee, his writing showcased "the mixture of rich picaresque novel and subtle analysis of our culture … developed by a commentator with a witty tongue and penetrating insight into the outer and inner complications that drive us to act, or prevent us from acting, and that can be called the dilemma of our age."

Read it today, and it's hard not to wonder what Bellow would have unleashed had he lived long enough to get a Twitter account.

In Cold Blood by Truman Capote (1966)

This was the first book that novelised a real murder, launching a new literary form that Truman Capote would call “the non-fiction novel”. In some ways, the story of how Capote investigated the story is as famous – and intriguing – as the story itself.

In November 1959 in the small town of Holcomb, Kansas, a wealthy farmer, his wife and their two young children were savagely murdered by shotgun blasts to the face. There were no clues and no ovious motive. Just bodies and blood. 

Capote saw the story in the newspaper. So, accompanied by his childhood friend Harper Lee (who had just finished writing To Kill A Mockingbird) he headed to Kansas three days later to investigate. Soon after, two men were arrested, and later condemned to death. During his visits to the prison where they awaited execution, Capote formed an unlikely bond with one of the killers, Perry Smith.

What emerged was a story that captured the American imagination, sold millions of copies and near-destroyed the author's life. “No one will ever know what In Cold Blood took out of me,” Capote once said. “It scraped me right down to the marrow of my bones. It nearly killed me. I think, in a way, it did kill me.”

Couples by John Updike (1968)

“Welcome to the post-pill paradise” is probably the most famous line in this lust-inducing novel about the sexual experiences of 10 perilously unfulfilled couples in small-town America. Actually, "lust-inducing" is not a strong enough word to describe Updike's sex scenes, which are copious. It is veritably purple.

Published at a time when America was in the steamy midst of sexual revolution, it peeled back the sheets on sex in suburbia. In fact, the story proved such a sensation in its graphic portrayal of adultery and promiscuity that it catapulted John Updike onto the cover of Time magazine.

“It was an ambitious portrayal of the first post-Puritan American generation, where money and the pill shaped the lives of 10 couples, all 'swingers' (a new usage in American culture) whose marriages were in varying degrees of disintegration, and for whom sex was a matter of cocktail party chit-chat,” wrote The Guardian in its 2009 obituary of Updike. In theirs, the Wall Street Journal called him “the high priest of sex and suburbia.”

Portnoy's Complaint by Philip Roth (1969)

Upon its release in 1969, Philip Roth's novel – about "a lust-ridden, mother-addicted young Jewish bachelor" who confesses his innermost sexual proclivities to his psychoanalyst – sparked a wildfire of controversy that ravaged polite society across the English-speaking world. It made Roth a household name.

The New Yorker greeted it as "one of the dirtiest books ever published". Life magazine called it a “wild blue shocker”, and the Australian government declared it a “prohibited import”. Central to the controversy was its graphic description of frenzied teenage masturbation, which had never been touched in mainstream literature before.

No household object seems safe from Alexander Portnoy's ravenous libido – not his dirty socks, not a cored apple, not an empty milk bottle, not even a “maddened piece of liver that, in my own insanity, I … violated behind a billboard on the way to a Bar Mitzvah lesson”.

As Philip Roth later recalled: “I got literary fame... I got sexual fame and I also got mad man fame. I got hundreds of letters, 100 a week, some of them letters with pictures of girls in bikinis. I had lots of opportunity to ruin my life.”

Slaughterhouse 5 by Kurt Vonnegut (1969)

By 1969 the Vietnam war was raging, and people's faith in the cause was fading. It was fertile soil for a cutting satire on the futility of war.

Slaughterhouse 5 spoke to millions as anti-war protests gathered pace and ground. The draft was two years old and the government was writing a cheque in young men's blood that the country couldn't afford. People were angry. Kurt Vonnegut was angry. He, after all, had seen the cruelty of war as a POW in Dresden when the allies firebombed the city at a cost of 100,000 civilian lives. So he wrote Slaughterhouse 5

It charts the life and times of Billy Pilgrim, an American soldier in the Second World War who is captured by the Germans and survives Dresden slaughter as a prisoner of war. As a result of shell-shock, Pilgrim becomes “unstuck in time”, doomed to revisit moments of his life over again.

The book flew off the shelves and became one of the most important anti-war novels of the decade, reflecting a widespread mood that would ultimately bring an end to the war in Vietnam.

It achieved that rare synergy of being a very funny (like all Vonnegut's work), and very serious, at the same time. It was, as Salman Rushdie wrote, a portrait “of a world that has lost its mind, in which children are sent out to do men’s work and die."

I Know Why The Caged Bird Sings by Maya Angelou (1969)

Maya Angelou’s life was little short of eventful. The author held various jobs, from sex work to showgirl, foreign correspondent to director. By 17, the point at which her debut book – and first memoir of seven – stops, she has given birth to her first child and survived a childhood all too heavy in sexual assault and trauma.

All this considered, though, it is Angelou’s portrayal of how the child Maya perseveres in the bitterly racist Deep South of the Thirties and Forties that made I Know Why The Caged Bird Sings such a resounding read in the midst of the Civil Rights Movement.

As the writer and journalist Gary Younge wrote: "Probably more than almost any other writer alive, Angelou's life literally is her work."

Do you agree with the books we've chosen? What would you have included? Let us know by emailing editor@penguin.co.uk.

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