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The Outsiders by S.E. Hinton (1967)

Long before Twilight or The Hunger Games, a schoolgirl named Susan was quietly inventing the YA genre by writing gripping novels of high school’s fearsome social hierarchies. The Outsiders was published when she was still just 18 - three years after she started it - and examines the gulf that has fuelled high school movies ever since: that between rich kids and poor ones. 

The working class ‘greasers’ and the well-to-do ‘socs’ are portrayed through the eyes of sensitive greaser provocateur, Ponyboy Curtis. Danger, drama and loyalties collide in a story that wholly excludes adults from the narrative. 

Catcher in the Rye by J. D. Salinger (1951)

For almost 70 years, JD Salinger’s Holden Caulfield has been a defining voice of (particularly male) teenage angst. A 17-year-old New Yorker with a problem with authority, Holden is chucked out of school and sets out in search of some spiritual truth as he rails against the 'phoniness' of adult life.

Catcher in the Rye remains one of the books that adolescents first fall in love with, capturing the uniquely human need for connection in a complex world, a book that perfectly encapsulates what it is to be young, sensitive and lost. It is also a book that, for many young readers, awakens them to the possibilities of literature.

Nineteen Eighty-Four by George Orwell (1949)

Paranoia, propaganda and a state of perpetual war form the backdrop to Orwell’s dystopian vision of a totalitarian future. In Nineteen Eighty-Four, the population is constantly monitored and manipulated in what Italian essayist Umberto Eco called ‘not negative utopia, but history.’ 

Written in 1948, the book’s ongoing relevance is demonstrated by the extent to which its concepts and terminology - Big Brother, Newspeak, DoubleThink - have seeped into our language. It teaches the importance of critical thinking and how everyone should rail against the machine. And, perhaps most presciently in our age of social media, how technology can be used for control.

Women, Race & Class by Angela Y Davis (1981)

The word ‘intersectionality’ may have come into popular use in the wake of Twitter-era feminism, but writer and activist Angela Y Davis was placing the women’s liberation movement through the prism of race and class a decade before most Gen Z readers were born in Women, Race & Class.

Davis tells the stories of the women’s suffrage movement and abolition simultaneously, giving a vital version of social and political history while pointing out the prejudice inherent to white feminism and telling the stories of pioneering black women.

Love in the Time of Cholera by Gabriel Garcia Marquez (1985)

This, simply, is one of the greatest love stories ever put to paper. It is so beautifully written that it transports you to another dimension, evoking an unrequited passion so powerful that it ties two people's lives together for half a century. 

In their youth, Florentino Ariza and Fermina Daza fall desperately in love. When, then, Fermina eventually chooses to marry a wealthy, well-born doctor, Florentino is devastated. But he never gives her up. In a time of Tinder, where modern dating moves at such a bewildering pace, it stokes the heart to immerse yourself in a world where love at first sight trumps love at right swipe.

The Bloody Chamber and Other Stories by Angela Carter (1979)

Think you know fairytales? Think again. Magical realist writer Angela Carter re-casts Little Red Riding Hood, The Snow Child (which inspired Disney’s Frozen) and Puss-in-Boots in new, dark and sexualised ways in this collection of short stories. The titular story is a particularly twisted one, in which a young woman discovers that her mysterious new husband is, in fact, a serial killer. Feminism, the power of women and the all-too-familiar ritual of femicide run through Carter’s glib and gothic retellings, making The Bloody Chamber an entertaining rattle through far more pressing matters than folklore.

On the Road by Jack Kerouac (1957)

This book has probably shaped more teenage attitudes towards travel, writing and even life itself than any other. Whether you read it in 1957 or 2020, On The Road is the quintessential coming of age novel. Long before air travel was commercially viable for most Americans, Kerouac tapped into peoples' romantic imaginings of life on the open road.

Sal Paradise, a young innocent, joins his hero, the mystical traveller Dean Moriarty, on an exhilarating ride across the United States and back again. Rich with hedonistic adventures such as riding freight trains, hanging out with hobos and drinking red wine under the moon, On the Road offers a definition of youthful lust for life: sex, drugs and one hell of a lot of jazz.

The Song of Solomon by Toni Morrison (1977)

'I remember reading The Song of Solomon when I was a kid and not just trying to figure out how to write, but also how to be and how to think,' said Barack Obama when awarding Morrison with the Presidential Medal of Freedom in 2012.

Set first in Michigan then across wider America, The Song of Solomon traces the growing up of Macon Dead, otherwise known as Milkman, as an African American in search of a better understanding of his heritage. This was the novel that placed Morrison (belatedly) on the map, and its original approach to slavery makes it essential more than 40 years on.  

Zen and the Art of Motorcycle Maintenance by Robert Pirsig (1974)

When ZATAOMM exploded onto the American literary scene in 1974, many thought it one of the most exciting books in the history of American letters. That's in spite, however, of Pirsig's manuscript being rejected by more than 100 publishers before it finally got snapped up - and went on to sell a million copies in its first year.

Why such a hard sell initially? Well, Pirsig's novel is thick with ideas and discussion, earning it comparisons to a philosophy textbook. If that's offputting, it's worth knowing that ZATAOMM is, at heart, a father-son narrative about life on the road. Read it for a moving and penetrating meditation on how we live… and on how to live better.

 

A Room of One’s Own by Virginia Woolf (1929)

It was nearly a century ago that master of Modernism Virginia Woolf published the stirring lectures she gave at Newnham and Girton Colleges, Cambridge, and yet her words retain their potency and determination even now. The title borrows from the lecture-cum-essay’s greatest takeaway: that ‘a woman must have money and a room of her own if she is to write fiction’ - ideally one with a lock and key.

During the course of this essential feminist text, Woolf examines the women who have been lost to history, and the difference their voices would have made to the wider historical narrative. She posits, famously, Shakespeare’s sister Judith, who could have been as great as the Bard had she been sent to school, rather than kept at home - much like Woolf. This is a piece of non-fiction that will make you feel lucky to read and, quite possibly, inspired to write.

Other Voices, Other Rooms by Truman Capote (1948)

Truman Capote may be more famous for In Cold Blood and Breakfast at Tiffany's, but neither are as good as his first novel, Other Voices, Other Rooms. Published in 1948, this strange and beautiful book rocketed Capote to literary stardom.

Set in the deep south, it begins with the arrival of 13-year-old Joel Sansom at a decaying plantation to meet the father he hasn’t seen in nine years. There follows a queer coming-of-age yarn for the ages where – amid the grotesques and creepy shadows of an old mansion – he discovers his identity through a wonderfully cryptic, often poetic, narrative woven with mystery and menace.

The Handmaid’s Tale by Margaret Atwood (1985)

It shocked readers upon release, earning a nomination for the 1986 Booker Prize, and then, more than 30 years later, astonished again with its eerie prescience and foreboding. The Handmaid’s Tale was Atwood’s sixth novel, but it undoubtedly made her name. Set in a worryingly near-future New England, but in a world that no longer has recognisable borders, women have been segregated by class and fertility to serve the male ruling class. Handmaids exist to bear the fruit of the near-infertile in a totalitarian regime. 

Atwood tells the open-ended story through the perspective of Ofglen, a Handmaid who gives a grim insight into the world where her freedom has been vanquished. When US television studio Hulu adapted the book in 2016, it shot back up the bestsellers charts and readers were swift to point out the resonances with contemporary and draconian discussions about fertility rights.

This Side of Paradise by F. Scott Fitzgerald (1920)

F. Scott Fitzgerald was 23 when he wrote this. Exactly a century on, and his prose still feels beautiful and elegant – even the hardest of young minds would struggle to resist.

The semi-autobiographical tale follows an idealistic Princeton student named Amory Blaine through his painful sexual and intellectual awakening. It is stuffed with great sentences that float from the page, such as this, which captures the innocence of young love: 'There is a moment – Oh, just before the first kiss, a whispered word – something that makes it worth while.'

 

If Beale Street Could Talk by James Baldwin (1974)

Shorn of history and context, James Baldwin's other novels could be cast as rungs on a ladder that If Beale Street Could Talk tops. A rhapsody of love in the face of a racist world, it is the first of Baldwin's books to focus exclusively on a black love story, and his only novel narrated by a woman.

Tish and Fonny are childhood friends-turned-lovers living in Harlem in the early 70s. When  Fonny is falsely accused of rape, Tish, who is heavily pregnant with Fonny’s child, sets out to prove his innocence. Baldwin, arguably one of America’s greatest writers, is adored as much for his crystal clarity of language as his belief in the transcendent power of love.

I Capture the Castle by Dodie Smith (1948)

Seventeen-year-old Cassandra Mortmain spends her days writing in her beautiful, if crumbling, family home, when the arrival of two handsome American brothers throws her family into disarray. A tender, complex depiction of first love (in all its joys and agonies), Dodie Smith's first novel is a heartfelt but never patronising tale that continues to resonate with teenagers (and adults) 70 years after publication.

The Bell Jar by Sylvia Plath (1963)

The Bell Jar

Fifty years before ‘autofiction’ turned up, Sylvia Plath turned her own battle with mental health, psychosis and depression into The Bell Jar. Published posthumously, a month after Plath died by suicide, the book has always lingered under a tragic pall, but its pertinence to younger readers is yet to wane.

Things start glamorously enough, with the young Esther navigating glamorous soirees and dashing men while working as a guest editor on a teenage fashion magazine. 

But The Bell Jar gradually descends into an examination of the lethargy and struggle of being a young woman who is not well, and being a young woman who rallies against the constraints of polite middle-class, middle-American society. Women of Esther’s generation are expected to give up whatever nascent careers they embark upon for marriage or motherhood; Esther just wants to write poetry. The bell jar of the title is one of suffocation and isolation, both from society and as a result of mental illness.

The Prime of Miss Jean Brodie by Muriel Spark (1960)

If we’re lucky, we leave school having learned a few lessons from a teacher that won’t ever turn up on an exam: how to make a good joke, how to stand up for yourself, how to bend the rules. These mentors make for ripe stories, fictional or otherwise, but even those who have experienced the real deal will find inspiration - and tragedy - in Miss Jean Brodie.

Muriel Spark’s name-making novella may have been set in the Thirties, but her spirit - of embracing her sexuality, of persuading girls to buck societal nicety - resonates today. Don’t be misled: Spark’s story is not a purely happy one; there is darkness and betrayal here, too. At barely 150 pages, it can be polished off in a weekend.

The Grapes of Wrath by John Steinbeck (1939)

This Pulitzer prize-winning portrait of a family torn apart by poverty and desperation in the Great Depression is one of the greatest of great American novels. It shocked US society and became a national sensation upon its publication in 1939, discussed on the radio, denounced by angry readers, and even banned in some libraries.

As their land grows arid and dry in the Dust Bowl, the Joads, a family of sharecroppers, decide to flee Oklahoma for California. What follows is an epic human drama of false hope, thwarted desires and the life-changing power of generosity, whatever form that may take takes.

To Kill a Mockingbird by Harper Lee (1960)

Harper Lee’s bildungsroman has become such a firm part of the canon that it can be easy to forget just how radical - and engaging - a read To Kill a Mockingbird is. In Scout, we have a rare thing for mid-century America: a young, female narrator. Spirited and outspoken, it is through her six-year-old eyes that we are introduced to America’s embittered race relations. 

In her father, lawyer Atticus Finch, Lee makes a character who has become a moral pillar in American literature. It’s her masterful managing of subjects such as rape, race and justice through a child’s perspective that has made Lee’s debut - and for 50 years, until the surprise publication of Go Set A Watchman, only - book near-mandatory reading in schools. In the era of #BlackLivesMatter, To Kill a Mockingbird remains as vital in its seventh decade as it ever has.

Wuthering Heights by Emily Bronte (1847)

Dreamy, gothic and wildly evocative, Emily Bronte’s only novel is a transportative read that lingers long after its final page. When the bereft Mr Earnshaw adopt a homeless boy, who is described as a ‘dark-skinned gypsy’ and named Heathcliff, it shatters his traditional Victorian family. Up on the windswept and isolated Yorkshire Moors, the Earnshaws and Heathcliff struggle against the torments of class and expectation as much as they do the relentless battering of the elements, painted vividly by Bronte. The forbidden, and ambiguous, connection that ensues between Heathcliff and Cathy Earnshaw, his adoptive sister, is the novel’s lifeblood, and has since inspired film adaptations - which have explored Heathcliff’s presence as a person of colour more fully - and, of course, Kate Bush’s song of the same name.

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