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45 Of The Funniest Books Ever Written

Some of the finest comedy tomes ever put into print

By Esquire Editors
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A genuinely funny book is one of life's simplest pleasures, but finding the real stand-outs is never as easy. Back in 2009, we asked some leading lights of comedy and literature to nominate the books that make them laugh out loud. Here we revisit the results, and add some extras from the Esquire team.

Such A Fun Age by Kiley Reid (2019)

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Picked by Esquire Editors

When stalled blogger and girl boss incarnate Alix moves to Philadelphia from New York, she employs graduate Emira as a babysitter for her three-year-old to try and get her book finished. But when Emira, who's black, takes Alix's white toddler to the supermarket, she's accused of kidnapping and things start to spiral out of her control.

There's big, squirm-inducing stuff here, especially when it comes to the excruciating lengths Alix and her husband go to to convince Emira – and themselves – that they're not racists. But Emira's inner life is so rich, and Reid has such an instinctively sharp and acid turn of phrase, that you're never far from a pearler. Take, for instance, a queasily over-familiar character described as "that one white guy at every black wedding who’s, like, super-hyped to do the Cupid Shuffle".

The Collected Dorothy Parker by Dorothy Parker

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Picked by Esquire Editors

Perhaps the most mercilessly, eyebrow-cockingly dry of the great Jazz Age humourists, there weren't many things Dorothy Parker couldn't sharpen with her witheringly sardonic outlook. This collection brings together poems, short stories, reviews and essays which showcase her wit.

But at the same time, you'll notice a river of sadness and yearning lurking just under the surface of her stories; the women at the heart of them tend grin in a slightly glassy-eyed way, attempting to make absolutely no waves whatsoever despite being cramped by the strictures of the society they live in.

A Short History of Tractors in Ukrainian by Marina Lewycka (2005)

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Picked by Esquire Editors

When 84-year-old Nikolai shacks up with Valentina, a much, much younger woman from Ukraine, his daughters Nadezhda and Vera – who have been estranged for some time – are dragged back together to work out how they can force this interloper out of their lives.

There's more than a little of the mid-Seventies whoops-a-daisy sitcom character about Valentina, but seeing as the whole point of Lewycka's story is to cut between low farce and high poignancy over Nikolai's experiences of famine, war and terror, she is at least at home here. One to tear through over a wet weekend.

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Me Talk Pretty One Day by David Sedaris (2000)

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Picked by Esquire Editors

Legally, we're not actually allowed to put together a lust of funny books without at least one David Sedaris entry. Ipso are very, very hot on that kind of thing these days. This collection of essays is split into two parts: the first is about Sedaris' upbringing in North Carolina and move to New York City; the second is about his move to France, and doomed attempts to learn the language and fit in. "Every day spent with you," his French teacher eventually tells him, "is like having a caesarean section." Magnifique.

The Pumpkin Eater by Penelope Mortimer

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Picked by Esquire Editors

An unnamed woman lies on a therapist's couch and outlines her perfect life with an architect husband, Jake Armitage, and an uncertain (but certainly exorbitant) number of children all living in a glorious mansion high above the city.

Or... is she? Soon, four-times-married Mrs Armitage is collapsing in Harrod's and losing her grip on herself. There's a woozy, unsettling feel to Penelope Mortimer's semi-autobiographical dissection of the emptiness which married life filled her with at the time. Bleak and acerbic, it's an acquired taste, but once you have it The Pumpkin Eater is uniquely, acidly funny. Mortimer was apparently so surprised by the first bit of good press she got for it, she promptly vomited.

And Away... by Bob Mortimer

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Picked by Esquire Editors

Yes, it's literally just come out. No, it's not too soon. Writing a good autobiography is a difficult thing to do, and it's stumped a lot of British comedians who you'd assume would be able to knock off something diverting quite easily. (Steve Coogan's is a case in point. Presumably he kept all the gags for Partridge's memoirs – see below.)

Bob Mortimer's early life wasn't much of a laugh – his dad died in a car crash when Bob was seven, and his teens and early adulthood were marked by overwhelming shyness and an LSD-triggered depression – but in spite of all that, it's intensely funny. He knows how to wring every drop of funny from an anecdote and in And Away... the full, unexpurgated story of how he rescued Jarvis Cocker from Michael Jackson's goons at the 1995 Brit Awards is, at last, set down on paper.

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The Idiot by Elif Batuman (2017)

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Jonathan Cape

Picked by Esquire Editors

One of the many staggering feats of New Yorker writer Elif Batuman’s sophomore novel is that, despite it detailing the love life of student Selin and a bunch of her equally self-absorbed peers studying at Harvard in the Nineties, you don’t want to throw it across the room. How can young people droning on about linguistics and dropping Russian literary references into every second sentence not be unbearable? Because of Batuman’s deft ability to undercut her characters’ pretentiousness at just the right time – and with observations that are honest and funny, but never mean – so that you can root for them right to the end.

Foreskin’s Lament: A Memoir by Shalom Auslander (2009)

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Picador

Picked by Esquire Editors

If you think the title of Shalom Auslander’s memoir about his youth in an ultra-Orthdox Jewish community in Monsey, New York, is a bit outré then, ooh boy, hold onto your yarmulkes because there’s more where that came from. In this feisty, hilarious and occasionally apoplectic account of his early familial and spiritual experiences, Auslander takes no prisoners, and that includes the Big Man himself (“This memoir makes The God Delusion look like a parish newsletter,” wrote one reviewer). If you enjoy it, you might try Auslander’s comic novel Hope: A Tragedy, about Anne Frank (yep, “comic novel”, you heard that right) or his most recent, Mother For Dinner, about cannibals. Not for the fainthearted, but oh so good.

The Adulterants by Joe Dunthorne (2018)

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Penguin Random House

Picked by Esquire Editors

There are some writers who, you sense, can write humorously only through self-torture; you can practically hear the painful tweaking and tuning of every line. And there are others for whom funniness just seems to spread across the page like a wash of watercolour, almost like they haven’t had to try. With his perfect balance of lightness and control, the British novelist and poet Joe Dunthorne is certainly among the latter, as his 2018 novel about a couple trying to get on the property ladder during the 2011 London riots reminds us. We’re not saying it’s actually as easy as he makes it look, but he pretty near has us fooled.

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My Sister, the Serial Killer by Oyinkan Braithwaite (2018)

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Picked by Esquire Editors

Long-suffering Korede and her younger sister Ayoola live in Lagos, Nigeria, and they have each other's backs. That's especially handy for Ayoola, because she's developed a habit of killing her boyfriends – she's just polished off her third – and needs Korede to help clean up. They have a good system, but it can't last. My Sister, the Serial Killer moves like a thriller – pacy and punchy – but at the same time it's laced with buckets of dark comic energy.

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The Catcher In The Rye by J.D Salinger (1951)

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Picked by David Nicholls

It's strange how this novel has become a by-word for doomy, nihilistic introspection; I blame Mark Chapman. It's actually a very funny book, right from its perfect opening sentence. No one has ever captured the adolescent voice with such accuracy; the pretension, the self-importance, the heart-breaking sincerity and misguided passion. The narrator's voice is perfect - slangy and wise-cracking - and there are some wonderful set-pieces too, including an excruciating encounter with a prostitute, wonderful rants about acting and the cinema and 'phoniness'. Hugely influential, cynical and warm and funny, its the perfect coming-of-age book (or bildungsroman, if you're feeling fancy).

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Love in A Cold Climate by Nancy Mitford (1949)

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Picked by Esquire Editors

This irresistible melange of love, family, sexuality and reads like the unbelievable creation of a bored housewife, while the impact is made in the gulf that exists between what people are thinking and what they are saying.

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 Delete At Your Peril by Bob Servant (2007)

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Picked by Irvine Welsh

Delete At Your Peril is a very, very funny book, and a perfect present for anybody who has a) a sense of humour, and b) gets irritated by internet spammers and their tiresome scams. Bob Servant, 62-year-old window cleaner, and Dundee's former cheeseburger kingpin, wages war on the scammers and their promises of easy money, love and gainfully employment. The hilarity comes from Bob's outrageous demands and the way he pulls the spammers into his own crazy, mundane and out-of-register world. You will piss yourself and then quote sections of this book repeatedly within your circle of friends.

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The Timewaster Letters by Robin Cooper (2004)

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Picked by Dan Davies

Spoon collector, thimble designer, professional fish fryer and world authority on wasps, Robin Cooper is a many of parts – and many incredibly silly but stupendously funny letters. Whether Cooper is organising a surprise clarinet party for his wife, designing scarecrows made from beef (“based on Roman themes, such as ‘the Storming of Thebes’ and ‘Brutus Avenged’.”) or offering his services to the National Cavity Insulation Association as their “Poet in Residence”, the Timewaster Letters contain some of the most outrageous requests and ridiculous drawings you are ever likely to see. Robin Cooper is the alter ego of BAFTA-nominated comedy writer Robert Popper and really should be a fixture in every gentleman’s toilet.

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The Bottle Factory Outing by Beryl Bainbridge (1974)

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Picked by Esquire Editors

As dark and doomful as it is hilarious, Beryl Bainbridge’s Booker Prize-nominated novel follows Freda and Brenda, two unlucky-in-love bedsit-mates working in an Italian-run wine-bottling factory in London, who find that their lives change forever after a team outing. Bainbridge based the novel on a miserable warehouse job she held in the seventies, which came with the added 'perk' of unlimited wine allowance.

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Based on a True Story by Norm Macdonald (2016)

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Picked by Esquire Editors

Stand-up veteran and former Saturday Night Live cast member Norm Macdonald inspires cultish devotion in the US, but never made much of a name for himself on this side of the pond. That's our loss. Late-night host David Letterman, a man who’s shared a stage with the biggest comedians of the past forty years, describes Macdonald as “funny in a way that some people inhale and exhale […] There may be people as funny as Norm, but I don’t know anybody who is funnier.”

His first and only book, Based on True Story, is an intentionally bewildering mix of memoir and pure fiction, tracing Norm’s life from his childhood farm in rural Canada, to the bright big-time lights of Rockefeller Plaza, to the bottom of his pocket at a Las Vegas craps table. Understated, supremely intelligent and lined with Norm’s trademark folksy charm and wit, this memoir/novel is the perfect introduction to a complicated comedy legend.

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The Secret Diary of Adrian Mole, Aged 13 ¾ by Sue Townsend (1982)

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Adrian Mole

Picked by Esquire Editors

The Secret Diary of Adrian Mole might just be British fiction’s most authentic insight into the hilariously hubristic mind of a teenage boy. That it was written by a middle-age woman makes such a feat all the more impressive. We peep in on this lonely suburban teenager’s private scribblings as he makes pseudointellectual observations about life, love and whatever he’s seen on the news that night, forever in the knowledge that he’s lying to himself as well as us. The series ultimately stretched over 8 books, finishing off with 2009’s The Prostrate Years, five years before author Sue Townsend's death.

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A Confederacy of Dunces by John Kennedy Toole (1980)

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Picked by Seb Hunter

If you can swallow the tragedy of its publication, then A Confederacy of Dunces is a comedic masterpiece whose pages sing with one of the greatest fictional creations in literature. Toole wrote the novel – set in New Orleans – in the early 60s, and his failure to find it a publisher led him to eventual suicide in 1969. (Its subsequent success and posthumous Pulitzer in '81 only compound the grim irony.)

The book follows obese savant Ignatius J. Reilly's doomed attempts to integrate with society – a Don Quixote of the Deep South – only with hot dogs for windmills. You'll buy copies for friends.

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Vile Bodies by Evelyn Waugh (1930)

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Picked by Alexei Sayle

It is a gift to the satirist to live in turbulent times but there still remains the task of encapsulating them. In Vile Bodies, an ostensibly superficial comic novel (Waugh wrote to Harold Acton, "It is a welter of sex and snobbery written simply in the hope of selling some copies") Evelyn Waugh brilliantly, hilariously, unflinchingly but always humanely pinions a society which is in thrall to gossip and decadence, traumatised by war and financial catastrophe yet unable to stop itself rushing headlong into further and deeper cataclysm. This is a book as much for our age as for Waugh's.

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The Life and Times of the Thunderbolt Kid by Bill Bryson (2006)

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Picked by David Mills

I had come to loath Bill Bryson, but on holiday a couple of years ago The Life and Times of the Thunderbolt Kid was the only book around. After three pages I was laughing aloud. When was the last time a book made me do that? Actually, 1989, The Lost Continent, Bryson's first book. In between, he had become hugely successful, but his books were increasingly lazy, stuffed with stereotypes, and crushingly formulaic: cosy chuckles for tedious old farts.

The Thunderbolt Kid captures the hilarious innocence of a time when men had flat-top hair cuts that left them "looking as if they were prepared in emergencies to provide landing spots for some very small experimental aircraft". There was an unbridled enthusiasm for all things atomic (from cocktails to motels and, of course, bombs) and unending culinary innovation, (spray-on mayonnaise, frozen salads, liquid instant coffee in a spray can).

The set pieces, such as Mr Milton diving disastrously from the high board ("He hit the water – impacted really is the word for it – at over six hundred miles an hour, with a report so loud that it made birds fly out of trees up to three miles away."), or the young Billy walking in on his parents having sex, still make me snort helplessly. I always put the book down happier than when I picked it up.

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