Brian Kiley has been a writer his entire professional career. He has penned jokes for his own stand-up act and for his longtime employer Conan O’Brien, whom he has been with since O’Brien’s original Late Night show. He is currently head monologue writer on Conan. And almost by accident, Kiley is now a novelist, having released his first book, The Astounding Misadventures of Rory Collins, in November.
The book started in a writing class Kiley took after moving to Los Angeles from New York when O’Brien took over The Tonight Show; it was supposed to be just an exercise. “I wrote what I thought was a short story,” he says. “And the teacher said, ‘Well, that’s not a short story, that’s a first chapter of a novel.’ ” Kiley said, “It is?”
He started adding chapters in his spare time, but it would soon become a daily pursuit. O’Brien’s tenure as host of The Tonight Show was short and fraught with drama, lasting only seven months. Kiley was in limbo. He knew O’Brien would eventually land another job and he’d be employed again, and he still had stand-up comedy, but he had no day job. He had just moved his family across the country and bought a new house and his wife had left her job.
Writing the book got him through a dark period. To keep himself going, he stuck to his morning routine of getting up and getting dressed, but instead of driving to a studio, he sat down to work on his novel. “When the whole Tonight Show thing happened and we were suddenly out of work, I didn’t want to just wake up and not shave and be in my sweatpants all day,” he says. “I would spend three or four hours working on it. It was good for me to have something to do to stave off the depression.”
It wasn’t that Kiley thought he’d never write a novel. He’s an avid reader of novels and history books, and he’d had a passing notion that he might write a book. In the past, he would write a few pages and then abandon the idea. With Rory, suddenly he was following through. “I think it was something that I always thought, ‘Someday I’m going to do this,’ ” he says. “And then it was like, ‘Oh, this is actually the day.’ ”
Onstage, Kiley is a kindly presence. He talks about his family and his daily life without being confessional. On Conan, he writes jokes for a mass audience that have to pass the muster of television censors. He is a first-class wit. Given his history, he has written a surprisingly dark tale. Rory Collins leaves a home with a suffocating mother who drove away his friends and potential dates (in one case, spray-painting “slut” on a young girl’s house under cover of darkness) and browbeat his father. In college, he has a brief career as an awkward lothario, helping equally awkward women lose their virginity. Then he finds himself in the role of a potential father and breadwinner.
The dark streak was a purposeful choice. “The jokes we write [on Conan] and the stuff I do in my act…is very light,” Kiley says. “I didn’t want to do that. I actually wanted it to be something kind of meaty.” To some degree, that surprised people familiar with Kiley’s career who read the book. “I think people were expecting it to be a jokey book. They were like, ‘Oh, this is actually a real novel as opposed to just characters saying jokes as they come in.’ ”
There are still plenty of funny moments and funny lines in the book, but Kiley was careful to make sure the humor wasn’t gratuitous. It had to arise naturally from the story and the characters. Looking to authors like John Updike and Richard Russo, Kiley sought to preserve a sense of believability and still find some laughs. “I read Richard Russo’s Nobody’s Fool, and all the dialogue is just insults,” he says. “ ‘Yeah, you cheap prick, when are you going to dust off your wallet,’ all that kind of stuff.” Kiley realized that “Oh, people do joke in conversation and that actually is realistic dialogue.”
Still, he says that “incredibly little” of the story is autobiographical. He did lose his mother to cancer when he was 22, which influenced the story. And while Kiley describes his mother as “quirky,” she was nothing like the family terrorist who is Rory’s mother. “It’s funny, because when they were talking to me about putting together the press release, the guy was like, ‘So, you decided to draw on your college experience,’ ” Kiley recalls. Not so, he insists. “I just kind of made the stuff up.”
When the book was finished, Kiley did shop it around, eventually finding management and an agent. He got good feedback from major publishers but the book never landed with them. “It was pretty positive, but nobody was quite willing to pull the trigger,” he says. His agent pushed for the book to get published, and it wound up with Beverly Drive Press, an imprint of Agency for the Performing Arts. He did a few rewrites before it was published, and his agency handled most everything after that, a process Kiley is unsure about. “I don’t get hung up on the details,” he says, laughing.
The book seems like perfect fodder for a quirky indie drama like Skeleton Twins or Nebraska. Kiley says his agents are shopping the idea, but nothing is forthcoming. “If Alexander Payne wanted to call me and work out something, I’d be more than happy,” he says. It’s an appealing idea to someone who spends so much time writing jokes about ephemeral topics, the events of a particular day or week. “We write our jokes and Conan does them, and then they’re gone and that’s it,” he says. “There’s nothing that I write that anyone’s going to want to see in a week or a month, never mind years from now. I would want to have something where I can say, ‘Yeah, I did this,’ and 20 years from now people will say, ‘Oh, I saw that movie.’ ” Kiley is also working on a follow-up novel, but no one should expect to see it anytime soon. “Unfortunately, now I have a job,” he says. “It kind of gets in the way.”
Nick A. Zaino III is a freelance writer based in Boston covering the arts for Kirkus Reviews, The Boston Globe, BDCWire.com, TheSpitTake.com and other publications.