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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.

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

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.

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

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).

3.Love in A Cold Climate by Nancy Mitford (1949)

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.

4.The Timewaster Letters by Robin Cooper (2004)

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.

5.The Bottle Factory Outing by Beryl Bainbridge (1974)

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.

6.Based on a True Story by Norm Macdonald (2016)

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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