The observation provided Tropper with more than just a celebrity story to tell his clients when he landed. It became the premise for his first book, Plan B (St. Martin’s Press), in which former college friends gather to help a movie-star classmate who is battling drugs. So one might partially credit (the future) Iron Man for inspiring Tropper, who had spent years unable to follow through on the stories he kept starting. And since that day, the New Rochelle, New York, native hasn’t stopped. Between 2000 and 2012, Tropper produced six novels, including the New York Times best-seller This Is Where I Leave You (for which he’s also writing the screenplay for Warner Bros.) and his latest, One Last Thing Before I Go (both Dutton Adult).
“There’s an element of wish fulfillment in writing about characters who get to say what they mean and break the rules.”
That’s enough to make any struggling writer hop a flight to L.A. hoping for a burst of inspiration. But the years since that plane ride have been equally vital. Tropper—like Tom Perrotta, Richard Russo, and Nick Hornby before him—has tapped into the minds of mostly suburban male protagonists who have “screwed up their lives or for whom circumstance has screwed [them] up.” And he always channels this literary state with a biting humor amidst the heartache. In One Last Thing Before I Go (recently optioned by director J.J. Abrams for Paramount), the protagonist—known simply as Silver—crashes his daughter’s friend’s bat mitzvah, takes the mike from the MC, and proceeds to make a tear-streamed apology to his little girl before he breaks into an impromptu song. Tropper calls the book perhaps his bleakest work, because much of the emotional damage done by Silver is irrevocable. But he believes that “with all the sadness and depression of being alone…there is a certain Zen that comes. I don’t know if you want to go to Buddha or Bob Dylan, but when you’ve got nothing, you’ve got nothing to lose. It can be liberating.”
Tropper certainly had nothing to lose as his writing career stalled throughout his twenties. Fresh out of Yeshiva University in 1991, he enrolled in the creative writing MFA program at NYU while simultaneously holding down his first day job, as a PR man at Ketchum Communications, where he touted products ranging from Evian water to Chlor-Trimeton allergy medication. He soon found office culture “suffocating” and, in school, discovered that something was missing from his prose. “You need some life experience to inform your writing,” Tropper says. “I didn’t really have anything to write about.” Disenchanted with both pursuits, he switched gears after grad school and devoted himself to designing jewelry display cases, which offered more independence. He was also fairly certain by then that he would never earn a living as a writer. But it was after that fateful L.A. trip that he finally found his voice—that of a man, around his age, dealing with the trials of a complicated family, fading dreams, and a track record of bad decisions. “It felt like a good engine to drive a book about a very early midlife crisis,” he recalls. “As I was approaching 30, I just felt like I’ve got to really give this a shot.”
The results were not overwhelming. While Plan B earned good reviews, his publisher wasn’t sure how to market his work, and it took him four more novels before he gained a significant following. Things shifted when he published 2009’s This Is Where I Leave You, about a dysfunctional Westchester, New York, family pushed together to sit shivah for their dead father. The Associated Press called it “artful and brilliant”; Publishers Weekly found it a “deliciously page-turning story”; and the Los Angeles Times pronounced the book “hilarious and often heartbreaking.” The hefty sales that followed were finally confirmation that he had not only found something to write about but, equally important, had connected with an audience. (Counted among them is Six Feet Under and True Blood’s Alan Ball, with whom Tropper is now writing and executive producing Banshee, a new action series premiering on Cinemax in January 2013.) The attraction for many readers may be that humor and pain circulate simultaneously throughout all of Tropper’s books; funerals, dangerous operations, and family meltdowns never go long without a few wisecracks thrown in. “There are moments of real darkness, but it’s just never gonna stay there with me,” he says. “I guess I just find the human condition kind of funny.”