After graduation, he snagged a job at the Voice, which he said has changed since, though one thing has remained constant: "whenever you were there was its heyday; whenever you left, it was downhill." He started out writing about television, branching out with more assignments until he was confident enough to start writing fiction.
His first novel was about a Gary Coleman-esque child star, which he had a tough time publishing. At this point, he played a segment of Donna Summer's "MacArthur Park" from an iPad, staring with deadpan solemnity into space, to show how sad he was when the rejection slips piled up. He said the lyrics are a metaphor for the artistic process, in which the artist assembles different ingredients to make a cake, which is then left out in the rain. And the artist will never have that recipe again. "The song poses an enigma," he cracked. "Who left the cake out in the rain? And why?"
After failing at writing—this book is still unpublished; he said he'll leave it to his daughter to sell in case she ever amasses large gambling debts—he considered other careers. "And here I call attention to my slender, delicate hands and my thin, feminine wrists." He considered pianist, hand model, and surgeon, but each had their flaws. He considered writing again, though it was a humbling prospect given the small amounts of literary fiction that are sold in proportion to the population of the planet. "You're not a gnat trying to get the attention of an elephant," he said. "You're a microbe in the butt of a gnat trying to get the attention of an elephant." But he had no choice; being a writer was deeply ingrained in his DNA.
Whitehead's history with Greenlight goes back to before the bookstore opened, when he read at a pre-launch event in 2008. "He's our neighbor!" beamed a woman from the shop during her introductory remarks. "I remember when this was just a dirty bodega where you could buy weed and Ajax," he said. "Just those two things." He read to an SRO crowd that crowded the store's whole front area.
His latest book, Zone One, is a zombie story set in New York City after an apocalypse. Its main character wanders the streets of Manhattan, remembering the city he once knew, seeing it as a palimpsest and feeling nostalgic—much as any New Yorker who has been here long enough does.
"It came to me in a dream," he said. In fact, he's been having anxious zombie dreams since middle school, when he saw Dawn of the Dead with his family. (The book is in the Romero tradition—the zombies don't run, nor are they called "zombies." He said anyone working within a genre had both to adhere to it and reinvigorate it.) His most recent zombie dream was two weeks ago. This dream was in 2009. He was staying at his country house, in a "bad emotional state" because he could hear his house guests having sex through the house's thin walls. His dream took place in Manhattan, where he wondered whether they'd swept out all the zombies so he could go out. This is a practical post-apocalyptic question, he said: zombies are hard to get rid of, like house guests.
"This is my second autobiographical work."