This list of 15 writers is so good I'll split it over two weeks.
What does it take to be a funny writer? Read here and learn
The 15 Funniest Writers of All Time:
Everyone needs to laugh. It’s pretty much the only thing that separates most people from fully succumbing to the overwhelming tragedy of it all. From the lowliest college student to the stuffiest, wealthiest CEO to the spacey young clerk at the local record store with an ironic moustache and creepy preoccupation with female bassists, we all need a chuckle now and then. Fortunately, all media lends itself to the distribution of yuks. Since reading is fundamental, this list focuses on the funny as it is written rather than as it is told in song, dance and on television.
As with all things creative, comedy comes burdened with a hefty load of subjectivity. What one finds riotously knee-slapping, another will scoff or take offense. So read this list as such rather than something definitive and solid. Anyone who grows irritated over omissions or inclusions should probably just step away from the internet for a while and reassess a priority or two. Follow an adaptation of the Mystery Science Theatre 3000 mantra – "It’s just an article. I should really just relax."
- Douglas Adams: The Hitchhiker’s Guide to the Galaxy series remains a classic of both science-fiction and comedy, with the initial radio series spawning five novels by Adams (and one by Eoin Colfer), a miniseries, stage shows, a computer game, comic books and a feature-length film. Even beyond that, though, he wrote a plethora of other essays and novels, with the Dirk Gently series comprising one of his more famous humorous contributions following the Hitchhiker’s juggernaut. With considerable cheek, wit and irreverence, he relentlessly prodded politics, religion and society, creating some delightfully absurd and memorable characters, situations and descriptions along the way.
- Woody Allen: Though known primarily as an influential, if not outright legendary, filmmaker, plenty of Allen’s short stories and essays stand up as some of his most essential works. "The Whore of Mensa" highlights many of his strengths as a writer and comedian. His familiarity with genre literature and films allows him to play with — if not outright subvert — the associated cliches and tropes. The descriptions and dialogue alike crackle with wry, dry delivery spiked with a tinge of neurotic tension, made especially apparent in the sample readings available on his website.
- Jane Austen: Contemporary audiences thrill to Jane Austen’s Regency romances, proclaiming them ever so sigh-worthy and clamoring to find Mr. Darceys of their very own. This mindset, unfortunately, entirely precludes the author’s status as one of the sharpest satirists to ever write in English. Beloved classics Emma, Pride and Prejudice and Sense and Sensibility all humorously pick apart English society, particularly the upper classes, and romances in a way that appears perfectly straightforward on the surface. Understandably, when the books have been completely and progressively further removed from their initial context, it is difficult for most first-time readers to pick up on their abject hilarity.
- Michael Ian Black: The State and Stella alum’s bizarre, surreal humor doesn’t appeal to every audience, but his blog and essay collection My Custom Van elicit liberal laughs from the people who find such things appealing. Best described as whip-smart dumb comedy, he gleefully parodies the raunchy observations of his "edgy" mainstream contemporaries — when he isn’t penning some of the silliest, most absurd prose this side of Monty Python, anyways. For fans who enjoy their Cracked splashed with few shots of McSweeney’s, Black is definitely a writer who needs to be read to be believed.
- Margaret Cho: Even factoring her stand-up and performance art out of the equation, Margaret Cho is a formidable comedienne. At a time when women receive wrong-headed dismissal regarding their capacity for humor, she challenges popular assumptions with acidic takes on gender, sex and sexuality, race, politics, body image, substance abuse and more. All of Cho’s works — comedic or not — provoke viewers and readers into thinking about serious issues, most especially her memoir I’m the One that I Want and the politically-charged I Have Chosen to Stay and Fight. Neither book is intended to be read as comedy, but her blog certainly delivers a regular dose of both humor and insight.
- Warren Ellis: Comic books comprise most of Warren Ellis’ literary output, with Transmetropolitan and Nextwave standing out as the most kinetic and gut-busting of the lot. Frenetic silliness characterizes his more hilarious offerings, with his only novel (as of now) toning it down slightly. Crooked Little Vein injects the writer’s fondness for bizarre, obscure sexual practices into a twisting, deconstructed noir narrative that easily equals his transhumanist and superheroic graphic fare. Even those who have yet to pick up any of Ellis’ printed works still pop over to his blog and Twitter feed for boozy, hyperactive good times.
- Sandra Hill: She writes romance novels involving time-traveling Vikings.
- Christopher Moore: Moore’s books overflow with humor, all of them his love of parody and deconstruction. As of this article’s publication, he has released eleven novels, most notably Lamb, You Suck, Fool and A Dirty Job. Like a hybrid of Terry Pratchett and his hero Kurt Vonnegut, he blends fantasy and humanism into such diverse narratives as a hitherto-unknown disciple dishing on Christ’s childhood and an everyman thrust into a career dealing in souls. At least three of his books have landed on bestseller lists, too — certainly a not-insignificant accomplishment.
Part 2 next week, and thanks again to guest post from Jasmine Hall of onlineclasses.org