The funniest books ever written, revealed

The first of five books in the Hitchhiker’s trilogy (there – that’s funny right off), Douglas Adams’s rip-roaring tale of Arthur Dent, Ford Prefect, Zaphod Beeblebrox, Trillian and Marvin the Paranoid Android has sold over 14 million copies to date. From the argument with the foreman before Dent’s house is bulldozed to Marvin reminiscing about being abandoned in a car park for half a billion years this is a remarkable, memorable and hysterical novel.

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That war is by and large a series of violent acts wreaked upon humans by other humans, under the auspices of humans with no wish to engage in such distasteful behaviour should highlight the madness involved. This of course makes it highly funny and ripe for satire. This is what Heller achieved in spades in his tale of Captain John Yossarian’s attempts to stay alive as World War II reached its climax. It is both brutal and comical as the best parodies often are.

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Oscar Wilde could have probably transformed the diary of a train spotter into a comedic work of genius such was his way with a quip and a couple of bon mots. So satirising the duplicitous nature of Victorian society was meat and drink to this master wordsmith. High farce with no real serious interest was the theme of the play, but cunningly this worked to Wilde’s advantage as he managed to lance the boil of pompous Victorian morals by using the softly softly manner of comedy.

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The ultimate scatological novel – or, as some wag had it, high literature reduced to a fart joke. John Kennedy Toole didn’t live to see his saucy tale of the faintly repulsive yet oddly endearing Ignatius J. Reilly published, but thanks to the persistence of his mother, we can all share in Reilly’s gaseous emissions and his attempts at obtaining gainful employment in New Orleans.

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P.G. Wodehouse was the quintessential British humourist of the 20th Century, and his legacy lives on in the works of Stephen Fry et al. We could have chosen any of his Jeeves and Wooster novels, but this, his third to feature Bertie Wooster and his valet Jeeves, is arguably the finest – and funniest – of them all. Wooster attempts to solve not one but two misfiring love affairs, has a run-in with a cold cucumber and there’s the strange case of the policeman’s helmet. Jeeves, as ever, is left to tidy up the mess. Classic upper class chortling.

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Intended as a serious travelogue of a boat journey between Kingston and Oxford, the hilarious scrapes that befall the three men soon gave Jerome his focus. Published in 1899, it captures an England on the precipice of the modern world, and yet the humour retains a fresh warmth to this day. Some of the incidents in the novel – not least trying to navigate the Hampton Court maze – have to be read to be believed.

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Everyone knows Nick Hornby does the irreducible minutiae of modern male life like no other contemporary writer – our angst, our foibles, our issues. But he also does laugh out loud funny. High Fidelity is his best example of this, as his protagonist Rob Fleming lurches from one ill-advised top five list to another. As a dissection of man’s inability to ‘grow up’, this is as painfully comic and wryly observed as it gets.

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There is something timeless about a fish out of water tale and that's exactly what Cold Comfort Farm is. Flora Poste is orphaned at the age of 20. Deciding to change her ridicuously privilaged life she heads to some relatives in the country, where she meets some of the strange elements of her family.

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Take two of the smartest, wittiest and most imaginative writers who have ever lived and ask them to dream up a book, and that’s Good Omens. Created by Neil Gaiman and Terry Pratchett, it’s a raucous mix of genres, including some magical realism, fantasy, occult and, as with much of their other work, an intelligent dash of comedy. This book follows the story of the eccentric angel Aziraphale and the irreverent Demon Crowley as the world falls apart. Once you’ve read the book, treat yourself to the Amazon Prime Video series.

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The first Adrian Mole book is an undoubted master class in comical teenage fiction. That a woman approaching middle age writes it only elevates the amusing tenor of the diary of a wannabe intellectual. Mole is that classic plot device – the unreliable and hubristic narrator who elevates his role in life. Just as entertaining are his observations on the national events of the time – the Falklands War and Margaret Thatcher’s administration chief among them.

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Spike Milligan made his name as a surreal comedian, so it’s apt that his debut novel should be such a bizarre and seditious delight. Set in 1924, against the backdrop of the Partition of Ireland, Puckoon is a village divided in two by some absent minded fools at the border commission who were thinking of the pub rather than their work. The Guardian claimed it has the funniest funeral scene in all fiction.

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One of the best debut novels of the last five years and also one of the funniest we have read in a long time, Eleanor Oliphant is Completely Fine charts the life of someone who is seemingly content with her rather boring life, until she saves someone's life with the help of a co-worker. At times hilarious, other time poignant - this is one special book.

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Christopher Hitchens – a man who knew a thing or seven about being funny – declared Kingsley Amis’s first novel the funniest book of the second half of the 20th Century. That’s up to you to decide of course, but we can heartily endorse Hitchens’s endorsement. Amis skewers many of old England’s societal conventions in his ribald novel of reluctant history lecturer Jim Dixon. The drunken lecture passage is worth the entrance fee alone.

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The male mid-life crisis is a rich playground for novels. The inherent comedic value in such a ludicrous Western capitalist notion gives authors room for plenty of manoeuvre. But to balance that with the needs of a weighty tome, that takes some skill. Russo has it in spades. Straight Man concerns the life of Hank Devereaux, an interim chairman of an English department. As he takes on his wife, the faculty, his daughter, his feelings for three women and the campus geese, Devereaux’s life slowly begins to unravel.

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That celebrated man of letters Dr Johnson famously opined that Tristam Shandy was ‘odd’ and would ‘not last’. How wrong he was. Sterne’s ribald The Life and Opinions of Tristam Shandy, Gentleman (generally referred to as plain old Tristam Shandy) is designed to be a simple account of Shandy’s colourful life. But from the opening passage through the 500-odd pages of drawings, jokes and diagrams (plus the odd blank page) this is a comedic masterpiece.

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The big screen adaptation is naturally hilarious, but Updike’s original source material is a wonderful exercise in satire. Three women in the Rhode Island town of Eastwick acquire witch-like powers after being spurned by their husbands. Swearing to wreak vengeance they run amok until the mysterious appearance of Darryl Van Horne. What follows is high farce and social satire rolled into one. Mischievous doesn’t begin to cover it.

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Trainspotting is many things – dark, violent, destructive and, erm, addictive – but above all else it is a tour de force of black comedy. Welsh’s gift for language, chiefly the ripe vernacular of those he writes about, is mesmerising. As such the misadventures that Rents, Sick Boy, Begbie and co embark upon is never less than caustically thrilling.

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Christopher John Francis Boone is a 15-year-old self-proclaimed ‘mathematician with some behavioural difficulties’. When he discovers the body of his next-door neighbour’s dog, Wellington, he embarks upon a journey of shocking self-discovery that shakes his fragile world to the core. If it doesn’t sound like a barrel full of japes, let us assure you this is a tender and funny novel.

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Ok, this isn’t a novel, it’s a travel book. But it’s a travel book penned by Mark Twain, quite possibly the funniest man ever to sit in front of a typewriter. Detailing his holiday to Europe and the Holy Land – famously dubbed his Great Pleasure Excursion – Twain unfolds a series of witty and unfortunate observations and incidents. For a Twain novel rich in humour try The Mysterious Stranger.

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Tom Jones – no, not the glorified Welsh warbler, thank God – is regarded as one of the finest comedic English novels. Jones is a feckless everyman who sets off to find his fortune in mid-18th Century England. In classic picaresque fashion, Jones comes across a rogue’s gallery of characters from both high and low society. The result is bawdy expose of life in England – a time no so dissimilar to now readers will discover.

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Slapstick is an underrated comedic device today. Shakespeare knew its worth though when he employed it marvellously in the aptly titled, The Comedy of Errors. Hinging on two sets of twins that were separated at birth, all manner of mishaps and farcical scenes abound when they are reunited. Academics today praise this work for its examination of social relationships. We love it because of the mirthful humour.

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Charles Dickens announced his quite voluminous talent with this hilarious set of comic episodes that befall the endearing ‘gentleman of leisure’ and founder of the Pickwick Club, Samuel Pickwick, Esq. Misunderstandings regarding marriage rub shoulders with a shooting expedition in Suffolk. Pickwick’s servant Sam Weller is another magically observed character.

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Yes, Skippy Dies. We know that from the title, and the book’s opening sequence. But this tragic incident doesn’t detract from Paul Murray’s amusing account of teenage life in a top Dublin boarding school. Daniel ‘Skippy’ Juster’s best friend, the irascible and rotund Ruprecht is attempting to visit an alternate universe, while their other friends just want to brag about their (obviously fictitious) sexual exploits. Both touching and funny – not always an easy combination to pull off – this is equal parts The Inbetweeners and A Confederacy of Dunces.

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If you like your humor to err on the satirical side, then pick up The Devil’s Dictionary. Although not fiction in the strictest sense, think of it as an alternative dictionary for word nerds and lovers of language. Originally named The Cynic’s Word Book, it provides playful definitions that simultaneously poke fun at the words themselves, society, and all of us. Ambrose Bierce was considered one of America’s first great writers and journalists, and his sharp wit comes across in every word entry. For example, the definition of bride, according to Bierce, is: “a woman with a great future behind her.”

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Most of us will have heard of the Bridget Jones's Diary movie, but did you know it was initially a novel? A top-rated, highly-popular, multi-million-selling novel at that. The film is faithful to the book, but don't let that put you off reading it if you saw the movie when it first came out in the early 00s. It's a funny, feel-good story about Bridget, a woman navigating her 30s and all the romantic escapades accompanying them. Some say it's satirical, others that it's tragic, and most that it's highly relatable. Regardless, it's a funny and touching book, and you'll miss Bridget once you get to the end – when you do, you can watch the movie sequel.

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Tina Fey is comedy royalty these days, but if you’ve ever wondered how she got started, read her autobiography, Bossypants. For years, Fey was a performer and writer on Saturday Night Live, starred in the hilarious hit TV show 30 Rock and penned many excellent comedies, like Mean Girls. This is her story, covering the difficulties of working in a male-dominated industry as a woman, her time on SNL, her pursuit of the traditional beauty idea and a near-fatal honeymoon incident. Tina's words are just as amazing and laugh-out-loud funny to read on the page as they are to see performed on the screen.

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Timofey Pnin is a Russian exile from his communist homeland and a Professor of Russian at a US college. As he struggles to come to grips with his new home a series of merciless mishaps and misfortunes unfold. As narrator, Pnin isn’t wholly reliable and Nabokov throws in a number of curve balls along the way to keep the pace odd and fresh. If you only knew Nabokov because of Lolita, read this and see a more curious side to the writer.

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Miss Pettigrew Lives for a Day is a joy of a read. The plot: an aging London governess is dismissed from her job, unfairly. She eventually gets another job looking after the sensational American actress and singer, Delysia Lafosse. What ensues is classic stuff.

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Yes, there’s the numerous passages devoted to masturbation techniques (one involving liver no less, but there’s more to Philip Roth’s feted book than how to jerk off. This is a dynamic, coarse and riotous novel that is framed around a monologue given by the narrator Alexander Portnoy to his psychoanalyst Dr Speilvogel. Emblematic of the times (it was published in 1969), this repudiation of societal norms was both uproarious and profound.

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Martin Amis, like his father before him, is a masterful exponent of gallows humour. This is abundantly prevalent in his expose of 80s greed and lust, Money. The antagonist ad director John Self is a comic character drawn realistically from the rampaging themes of the age – hedonism, avarice and sloth. Amis cleverly extracts humour from Self’s misadventures by both poking fun at and revelling in his woes. Marvellous.

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With its exploration of race and how this shapes you as a person, there are heady themes in Oreo but the story of mixed-race Oreo who goes searching for her white Jewish father in New York is startling in its wit and wisdom. While it was written in 1974, it's a book that still resonates today and probably more so than when it was first released.

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Much like Trainspotting, the characters in American Psycho are amoral scoundrels – it’s just that they operate at a higher social stratum. However, even though the vainglorious Patrick Bateman and his chums Timothy Price, Paul Owen, Craig McDermott are loathsome individuals, there is also an earthy humour to their bland lives. You might not like yourself for doing so in the middle of a graphic murder, but you will laugh more than you will recoil in horror.

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The skeleton in the cupboard indeed. This piece of fiction set London’s literary set ablaze when it was published in 1930 because it was said to be a thinly disguised account of the recently deceased Thomas Hardy’s slightly scandalous personal life. Maugham spectacularly spears social snobbery and boorish behaviour in this ribald tale.

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This book isn’t one long story but a very witty, brilliant, funny collection of essays from the renowned Nora Ephron. Her comedy and wisdom leap off the page, which isn’t a surprise considering she’s the writer and filmmaker behind many of the most loved romantic comedies, like When Harry Met Sally. It’s written by a woman, primarily about women’s experiences, but that shouldn’t stop men from reading it, too, as it covers universal topics, like ageing.

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Anyone who grew up in Britain during the 80s will immediately get this hilarious coming of age tale – a bildungsroman in literary parlance. Jason Taylor is a 13-year-old boy trying to make sense of the world in Worcestershire in 1982. As the adults – notably his parents – seem to collude in the art of self-destruction, Jason is left trying to work it all out. The language and references are spot on, and the abundant comic set pieces prevent this truthful tale from the author of Cloud Atlas staggering into melodrama.

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No ordinary novel, Illywhacker is divided into three books of 86, 61 and 66 chapters respectively. It tells the story of Herbert Badgery’s vivid life, from his exploits as a conman to time spent inside for ripping the finger off his childhood Chinese mentor. The prose is vibrant, bright and witty, as Badgery’s tales – and that of his son Charles – unfold in a meandering and light-hearted fashion.

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Sebastian Dangerfield is one of literature’s finest rascals. A borderline intellectual with raffish boho pretensions who can’t stop himself from getting blind drunk at any opportunity or trying to get into the corset of every young woman he meets. Banned in the US and Ireland upon publication for obscenity, it is one of the finest – and certainly funniest – novels you will ever have the privilege of devouring.

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The opening chapter of ex-wrestler-cum-comedian-turned novelist Mick Foley’s first book is among the funniest ShortList has ever read. Rare are the books that induce involuntary chortles on the bus – this one achieved it five times in one dazzling sequence. The book concerns the life of Antietam (Andy) Brown V and his wayward father Antietam (Tietam) Brown IV: it is raw, unflinching and always painfully funny.

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A lurid journey into self-obsession, or a marvellously post-modern account of one man’s colourful dreams? The jury is still out on James Joyce’s much-debated novel, but what can be categorically agreed upon is that Finnegan’s Wake is strangely beguiling piece of sardonic literature. Just don’t ask us to tell you what it all means.

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Those of you who have gotten their Woolf fix through classics such as To the Lighthouse and Mrs Dalloway might be a little surprised to read that she can also write some fantastically hilarious prose. Case in point Orlando - a highpoint of queer fiction that charts a titular character who, over the course of some 400 years changes sex from male to female and gets in a huge number of adventures. Nigel Nicolson calls Orlando "the longest and most charming love letter in literature" - it is, but it's also side splitting in places, too.

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