Is Moby-Dick gathering dust on your shelf? Andrew Hankinson reveals why it’s finally time to conquer it, and 13 other daunting reads

Everyone has them; those thick tomes with tiny type that have edged open windows, propped up wobbly tables and weighed down loose paper. You’ve done everything with them — except read them. They invoke fear. It’s their size, their daunting literary baggage, their impenetrable language — and the very real prospect that if we were to attempt them, we’d spend approximately 4.5 days re-reading passages and another 12 hours looking up obsolete words in the dictionary before suffering a crushing sense of defeat when we finally commit it back to the bookshelf.

But this is a call to arms. Five ShortList members of staff are going to attempt to conquer the most testing novels written — follow how we fare here. So it’s time to unearth that hefty work of intellectual brilliance, blow off the dust and show those titans of literature who’s boss.

(Main image: Alan Murray @ GeorgeGraceRepresents.com)

Moby-Dick by Herman Melville (1851)

Page count: 720

What it’s about: The narrator joins a whaling ship captained by Ahab, who wants to catch a certain white whale (Moby-Dick) that took his leg. Despite long digressions about the whaling trade, Ahab’s descent into obsessional madness is gripping.

Why read it: “Melville was a visionary who poured everything into this book, which starts as a realistic account of a whaling journey and goes out of control, heading in every imaginable direction, including the nature of evil,” says Simon Winder, a publishing director at Penguin. “It’s chilling.”

First line: Call me Ishmael. [Read the first chapter of Moby-Dick on our new tablet app at Google Currents.]

A Brief History of Time by Stephen Hawking (1988)

Page count: 256

What it’s about: The fundamental questions of physics and our existence tailored to a non-genius audience. Topics covered include gravity, black holes, the Big Bang and the nature of time. The book occupied the bestseller list for several years.

Why read it: “Hawking made physics accessible, which is a great thing,” says author Will Self. “I only did physics up to O-level, but after reading this I can understand what I now read about theoretical physics at an upper-popular level. That’s not bad.”

First line: A well-known scientist (some say it was Bertrand Russell) once gave a public lecture on astronomy.

Little Dorrit by Charles Dickens (1857)

Page count: 912

What it’s about: William Dorrit is being held in debtor’s prison Marshalsea, where Dickens’ father was once jailed. While Dorrit spends years locked up, his daughter — Little Dorrit — tries in vain to pay his debts. A satirical work that takes a swipe at HM Treasury and Britain’s burgeoning industrial workplace.

Why read it: “It fits with the current crisis,” says Winder. “As an attack on banking, it’s brilliant. The heart of it is the corruption surrounding the bank, where everybody is refined and upper-class when, actually, they’re rotten to the core.”

First line: Thirty years ago, Marseilles lay burning in the sun, one day.

Don Quixote by Miguel de Cervantes (1615)

Page count: 1,008

What it’s about: A comic tale of a humble man who fashions himself as a chivalrous knight and sets out on many adventures. In 2002, it was voted best novel by 100 modern authors.

Why read it: “Hamlet, Michelangelo’s ‘David’, Bach’s Mass In B Minor, Van Gogh’s ‘Starry Night’... Don Quixote: this novel’s influence on Western culture is incalculable,” says Jonathan Ruppin, web editor at Foyles and judging alumnus for the Costa book prize.

First line: Somewhere in La Mancha, in a place whose name I do not care to remember, a gentleman lived not long ago, one of those who has a lance and ancient shield on a shelf and keeps a skinny nag and a greyhound for racing.

War and Peace by Leo Tolstoy (1869)

Page count:1,440

What it’s about: The story of five aristocratic families during the French invasion of Russia, told (mostly) in the manner of modern historical fiction. Unfortunately it’s now popularly known as a bad punchline — “What are you writing, War And Peace?”

Why read it: “Some of the passages of Tolstoy’s theories on Russian history are slow,” says Self, “but he’s one of the greatest writers of all time, and it’s all in here. Also, I once used Tolstoy to insult Richard Littlejohn [during a radio interview], which is reason enough for Tolstoy to exist, don’t you think?”

First line: “Well, Prince, so Genoa and Lucca are now just family estates of the Buonapartes.”

Foucault’s Pendulum by Umberto Eco (1988)

Page count: 656

What it’s about: Three Italian editors play a game creating a super-conspiracy linking major events in European history, attracting attention from real conspiracy theorists who want to know the truth at all costs.

Why read it: “Eco’s book is a satire on conspiracy theories and the obstinacy of those who believe them,” says Dr Florian Mussgnug, lecturer in Italian literature at UCL. “It is also a poignant and compassionate portrait of a generation who too quickly abandoned radical politics in favour of New Age occultism. And Eco’s wit, lucidity and love for detail show in every page of the novel.”

First line: That was when I saw the Pendulum.

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

Page count: 432

What it’s about: A man takes his son on a 17-day motorcycle journey. Along the way he discusses philosophy, his past and what is meant by ‘good’.

Why read it: “I read it when I was 18 driving around America with a friend,” says William Skidelsky, books editor at The Observer. “It’d be good to read on the train as it’s transporting and he’s an engaging writer. There’s plenty of teenage philosophising on the meaning of the world, but it’s down to earth at its core.”

First line: I can see by my watch, without taking my hand from the left grip of the cycle, that it is eight-thirty in the morning.

Underworld by Don DeLillo (1997)

Page count: 832

What it’s about: Nick Shay is a waste-management executive with a sinister past and a wife who’s having an affair. The novel spans his life, wider historical events and the lives of the famous, using a baseball as the constant link between people and time. A 2006 survey of authors and critics by The New York Times voted it runner-up for best American novel of the previous 25 years (Toni Morrison’s Beloved came first).

Why read it: “He’s good about the modern world in a way that nobody else is,” says Matt Thorne, author, screenwriter and book reviewer. “It’s incredibly stylish prose, far better than The Corrections [by Jonathan Franzen], and I’d say that, along with Infinite Jest, it’s one of only two modern books that has any claim to being the Great American Novel.”

First line: He speaks in your voice, American, and there’s a shine in his eye that’s halfway hopeful.

Crime and Punishment by Fyodor Dostoevsky (1866)

Page count: 576

What it’s about: A young Russian intellectual living in poverty sells his possessions before killing his pawnbroker. His guilt turns the story into a psychological thriller about human conscience.

Why read it: “Russian literature’s intimidating reputation is based on its length and often vast cast of characters,” says Ruppin. “Crime And Punishment was a landmark in social realism, and the moral dilemma has universal resonance.”

First line: On an exceptionally hot evening early in July a young man came out of the garret in which he lodged in S Place and walked slowly, as though in hesitation, towards K Bridge.

Ulysses by James Joyce (1922)

Page count: 1,040

What it’s about: Two men — writer Stephen Dedalus and advertising canvasser Leopold Bloom — whose lives intertwine during the course of a single day in Dublin (16 June 1904). Except the ordinary is then turned extraordinary by Joyce’s refusal to shy away from anything, particularly the darker and ruder bits of humanity. Some people are put off by his continual style changes, but the language is crystal-clear.

Why read it: “I’m a late Joycean and didn’t manage to read all of Ulysses until my thirties, but it was worth the wait,” says Self. “Incontestably, it’s the most powerful and important 20th-century novel I’ve read: the equivalent, in terms of the multi-dimensional representation of the human consciousness, of Stephen Hawking’s multi-dimensional analysis of matter and energy.”

First line: Stately, plump Buck Mulligan came from the stairhead, bearing a bowl of lather on which a mirror and a razor lay crossed.

2666 by Roberto Bolaño (2004)

Page count: 912

What it’s about: Five sections with different characters and settings, all linked to a Mexican city where 300 young women have been murdered. It’s based on the real town of Ciudad Juarez, where thousands of women have been murdered or gone missing in the past 20 years.

Why read it: “It’s a fantastic book,” says Skidelsky. “One of my all-time favourites. It’s long, there are lots of digressions and some of it’s weird — even utterly mad — but it’s a great read.”

First line: The first time that Jean-Claude Pelletier read Benno von Archimboldi was Christmas 1980, in Paris, when he was nineteen years old and studying German literature.

Infinite Jest by David Foster Wallace (1996)

Page count: 1,104

What it’s about: Set in a future North America, the plot ‘focuses’ on a halfway house for addicts, a tennis academy and an attack by separatists from Quebec, wrapped up with famously sprawling footnotes. Wallace was only 33 when he wrote it.

Why read it: “It’s completely bananas,” says Winder. “There’s no way of describing it accurately. It’s very, very funny. Wallace was an incredibly good tennis player, but it’s not a book about tennis. It’s a kind of excuse to write about pathological behaviour. He was a charismatic and amusing guy.”

First line: I am seated in an office, surrounded by heads and bodies.

Remembrance of Things Past by Marcel Proust (1927)

Page count: 2,656 (Parts I & II)

What it’s about: A narrator reflects on his life and tries to understand it. One of the longest novels ever written, it took Proust more than a decade to complete.

Why read it: “I read it in my twenties when I was living in Australia,” says Self. “The contrast between the etiolated manners of the Faubourg Saint-Germain and the barfing and boozing around me was salutary, to say the least. Page length sentences din into the growing brain the complex stratigraphy of human culture and psychology, but — and here’s the pay-off — it’s laugh-out-loud funny.”

First line: For a long time I used to go to bed early.

The Age of Extremes: The Short Twentieth Century, 1914–1991 by Eric Hobsbawm (1994)

Page count: 640

What it’s about: A history of the world from 1914 to the collapse of the Soviet Union in three phases.

Why read it: “This should be a set read for anyone in public office,” says Ruppin. “The look at humanity’s progress to enlightenment addresses issues beyond modern political discourse.”

First line: On the 28 June 1992 President Mitterrand of France made a sudden, unannounced and unexpected appearance in Sarajevo, already the centre of a Balkan war that was to cost many thousands of lives during the remainder of the year.