Twenty before Twenty: What to Read When Late-Teenage Angst is in Full Swing

From what I remember, being a teenager was being in a constant state of change and anxiety. Existentialism weighed heavy – even though I didn’t yet know what name to give that feeling. If you know a teenager, or are indeed one yourself, this won’t be much of a surprise.

Obviously, some teens emerge from teen-dom unscathed, skipping merrily into their twenties with nary an acne-riddled memory in common with their not-so-hormonally blessed counterparts. Good for them; we’ll meet them at the twenty-year high school reunion and until then reserve judgment.

I have compiled this reading list for the other category of teen; the kind who needs outsider confirmation as well as affirmation of their innermost misanthropic worldview. I’m not saying that all these books are relatable to the teen experience, in fact, very few of them deal with anything remotely teenage, but respectively, I think each of the following titles say something important about the human condition. All offer unique insights and contextualise the concepts of longing, passion and despair  in a way that might just set off a powerful  chain of thought in the teenage reader; harnessing possible negative thought patterns and channelling them into critical thinking. Because ultimately it’s what you do with the thoughts and feelings that count, isn’t it?

If you happen to be one of those happy-go-lucky teenagers I mentioned earlier and fancy giving these books a whirl, your life is your own, knock yourself out! There is plenty of sex in some of them, and to make things easier I will hereto mark the most gratuitous of them with an asterisk (or two), if they are particularly racy.

less than zero

20. *Less Than Zero, by Bret Easton Ellis

Whatever thoughts you’ve had can’t be as bad as what the teenagers in this debut novel actually get up to.


a confederacy of dunces

19. A Confederacy of Dunces, by John Kennedy Toole

A posthumously published picaresque ode to disenchantment and adult failure. This is a truly brutal assessment of the life of a weirdo.


the bell jar

18. The Bell Jar, by Sylvia Plath

Suggested year 13 reading for a reason. A roman-à-clef portraying the protagonist’s descent into mental illness. Bold, yet subtle, and way ahead of its time.


crime and punishment

17. Crime and Punishment, by Fyodor Dostoevsky

Don’t be dissuaded by the sheer density of this book; I know I was for years, mistakenly thinking that Russian authors were too wordy and impenetrable. A simple word structure belies the true complexity of themes such as anihilism, alienation and justice.


howl16. *Howl, by Allen Ginsberg

Social commentary and revolutionary manifesto of the beat generation.



junky15. Junky, by William Burroughs

The high highs and the low lows of trying to score in New York. Is there a modicum of shame or guilt running through these characters? Questionable, but there is a whole lot of drugs.


fear and loathing 14. Fear and Loathing in Las Vegas, Hunter S. Thompson

Another roman-à-clef; chasing the American dream across America in a drug-fuelled haze. This one might make you want to consider Gonzo journalism as a career option. Resist that urge.


on the road13. On the Road, by Jack Kerouac

Based on Kerouac’s travels across America and considered to be one of the defining novels of the beat generation.


post office12. *Post Office, by Charles Bukowski

Bukowski’s first and finest work.



rabbit run11. **Rabbit, Run, by John Updike

Chasing the American dream, and finding it lacking, Harry “Rabbit’ Angstrom is one of the most thought provoking characters in modern American literature.


where I'm calling from10. Where I’m calling From, by Raymond Carver

A short story that takes place at an alcohol rehabilitation centre and meditates on the oftentimes cathartic process of storytelling.


the secret history9. The Secret History, by Donna Tartt

College friendships become sordid and obsessive, a terrible crime is committed, but who can be held accountable when anything among this group of bookish eccentrics seems infinitely permissible?


the human stain8. **The Human Stain, by Philip Roth

For forty years Professor Nathan Zuckerman has hidden a secret of such magnitude that it has completely altered the course of his life. This novel explores the duality of public and private life with deft realism as well as a poetic turn of phrase.


atonement7. *Atonement, by Ian McEwan

Exploring the concepts of misinterpretation as well as innocence and naivety, eight year old Briony makes a choice that is to have devastating consequences.


metamorphosis6. The Metamorphosis, by Franz Kafka

With the first lines being: When Gregor Samsa woke up one morning from unsettling dreams, he found himself changed into a monstrous vermin…; you can’t say that’s not at least a little intriguing.


never let me go5. Never Let Me Go, by Kazuo Ishiguro

The friendships formed in this dystopian universe, where people are cultivated solely to be used for replacement body parts, run deep as well as shallow and expose the frailties and ineffectiveness of a lot of human communication.


fight club4. *Fight Club, by Chuck Palahniuk

How could any Top 20 not have this gloriously obscene book listed? Go and read the book, because the first rule is: we’re not allowed to talk about Fight Club…


the outsider3. The Outsider, by Albert Camus

A nihilistic little tale of a fatalistic little man.



19842. 1984, by George Orwell

A totalitarian society ruled by Big Brother, with thought crimes punishable by forced exile into the infamous Room 101. 1984 reads like a contemporary dystopian novel, remaining fresh and exciting some sixty years after first being published.


lolita1. Lolita, by Vladimir Nabokov

Lolita would arguably still be the greatest book of all time, even if one were only to read the first magnificent chapter. Vladimir Nabokov tells the tale of a middle-aged man, his sick desire and mad passion for a twelve year old girl with such alarming detail and warped clarity that it is at once heartbreaking and creepily disconcerting all in the same paragraph.

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Chelsea Lee is a twenty-something university dropout. She has a penchant for 80s synth pop. She lives, reluctantly, in Auckland and enjoys the works of miserable existentialists and misanthropes.

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