Michael Chabon, Wonder Boys (1995)
Scratch a novel about a novelist, and you'll find a novel about a novelist who can't finish his novel. And isn't it suspicious that so many of them are sophomore efforts? Almost makes you think the writer is writing his way out of his character's disease. Michael Chabon followed up his first surprise hit, The Mysteries Of Pittsburgh, with this tale of childhood friends gone to seed. Grady Tripp is a professor-slash-author whose Great American Novel has ballooned to 2,000 pages with no end in sight. He's goaded to unaccustomed action when his drunken, promiscuous editor informs him that the publishing house is about to fire him. When Chabon's sprawling The Adventures Of Kavalier & Clay appeared five years later in 2000, it seemed to be a clear analog to Tripp's Wonder Boys (the novel within the novel). Thank goodness it didn't take Chabon decades in academia and three failed marriages to complete it.
Chuck Palahniuk, Haunted (2005)
That philosophy about why novelists write novels about novelists writing novels takes on yet another layer of depth in Haunted, the latest from Fight Club author Chuck Palahniuk. The action starts in a writers' retreat, where 17 wannabes retire away from the world's eyes to create their masterpieces. But it turns out that the only stories they have in them are their own sordid histories of botched masturbation, cannibalism, corpse-desecration, and many more such horrors. As the book progresses, these stories emerge, and they start a new, more visceral writing project: rewriting history, with them as the victims of the people running the retreat. Looking forward to their imagined fame, they torture themselves and each other so they'll have plenty of shocking material for their imagined bestseller tell-alls. Rarely have the self-destructive aspects of writing—the isolation, the self-examination, the mining of personality for useful tidbits to offer the world, the exposure that follows—been made so literal, or so relentlessly graphic.
Michael Connelly, The Poet (1996)
When Denver crime reporter Jack McEvoy sets out to investigate the suicide of his cop brother, he discovers that the death might be the handiwork of a fiendishly clever serial killer. Soon, the journalist comes up against a different kind of deadline! Or something like that. Michael Connelly's bestselling thriller set a new standard for the murderous-genius genre—one so swiftly imitated that it's doubtful anyone could ever adapt The Poet for the big screen without being accused of ripping off the stories that came later. But what gives the book its flavor is the way Connelly describes what it takes to write for a daily paper and solve mysteries without a badge. It's a process Connelly knows well from his own days working the murder beat—though presumably he never had to file his stories under any literal gun.
Stephen King, Misery (1987)
Stephen King has practically made a cottage industry out of books about troubled writers in the act of writing: The Shining, The Dark Half, the new Lisey's Story. He even wrote himself into his Dark Tower series, and turned his act of writing the books into a plot-significant point. But his most memorable exercise in writing about writing remains Misery, in which a bestselling pulp novelist winds up helpless in the hands of a dangerous psychotic who considers herself his biggest fan. After addicting him to painkillers and isolating him from the outside world, she demands he write a novel resurrecting the popular character whom he just killed off. To save his life, he complies. King has recently said that looking back on the book, he realizes it was about his drug addiction in the '80s, and his attempts to escape it; to be fair, the book does feature a great deal of detail about the difficulty of dealing with addiction and the pleasures of surrendering to it. But it can just as easily be read as a none-too-subtle expression of King's discomfiture with fame, and with his own often-rabid, often-creepy fandom. It's still an excellent beach-blanket thriller 20 years after its first publication, but it's also a highly personal book, even by the high standards of "personal" usually set by writers-writing-about-writers books.
Bret Easton Ellis, Lunar Park (2005)
Writing his own version of a Stephen King domestic horror novel, Bret Easton Ellis copies King's author-as-tortured-hero motif so precisely that it verges on parody, right down to the way Ellis takes a mundane around-the-house object—in Lunar Park's case, a stuffed toy—and turns into something menacing. The real horror, of course, is Ellis himself, here playing a character in his own book, trying to get some work done while surrounded by sexy students, nagging celebrity wives, family ghosts and a cloud of illicit chemicals.
Vladimir Nabokov, Pale Fire (1962)
Nabokov's lovely classic Pale Fire isn't just a book about writers writing, it's also a book about rewriters rewriting. In an intricately nested story, Nabokov presents an epic poem about death and the possibility of the afterlife, ostensibly written by an American poet, John Shade. Then he presents the story of how the poem came to be written, and how it came into the hands of Shade's neighbor Charles Kinbote. Finally, Kinbote presents his own editorial explanation of the poem, recasting it all as a metaphorical image of Kinbote and his homeland. Many interpretations of the book have been offered, but the entire thing works beautifully as a smart, skillful satire on the way well-meaning scholars dissect and deconstruct literature, sometimes warping it unrecognizably. On some level, it's a tremendously sad book, raising the question of why writers bother at all, since their intentions may not survive them, and their works become vulnerable the moment they leave the brain and hit the page. But in spite of all the misinterpretation and willful predation, Pale Fire is still a wryly hilarious book, particularly as a portrait of writerly delusion and self-aggrandization.