Selected for Best American Magazine Writing twice (2004 & 2009), named by Sport as the "best golf writer you never heard of," Chiarella's work has further been cited in Best American Essays, Best American Travel Writing and Best American Sports Writing.
In 2005, he held the post of as Fiction Editor of Esquire, publishing the works of Stephen King, Daniel Woodrell, Ralph Lombreglia, Chris Adrian, James Lee Burke, Gary Shytengart and others.
In summer of 2011, he worked as a Consulting Producer in the development of the new Rosie O'Donnell show, returning to Esquire at the close of that summer.
at a clamshell table, a setting spread open to the room like a huge embrace, in a big glassy Italian restaurant on Beverly Boulevard in Los Angeles. That is Rule One of celebrity-profile writing: Ignore yourself. I grew up in upstate New York, where what you know as Buffalo sauce was invented. So it turned out that the big girl with the sparkling headband was right. Two years ago, you couldn’t buy a decent chicken wing anywhere within a 30-mile radius of Greencastle. But the moments before meeting the subject are like a low-grade migraine, like sleeping on a nervous mattress. I step into the restaurant, climb into the car, ring the bell.
By midsummer, with the heat and the burned-out lawns, even the Dairy Castle—you know, sucking on chili dogs and all that crap—starts to feel like a pretty good option.
The night before, Gosling had told me—unequivocally— that he believed he’d grown up in a haunted house.
Sometimes, I really do think it is that place that Ryan Gosling suggested. The next day, he backed off, hemming and hawing about stories his mother had told him. Like there was no doubt.” This is another rule: People have a right to change their minds.
He periodically writes an on-line column for called "Advice About Women." Twice a finalist for the National Magazine Award, he won in 2009 as part of an Esquire writing team for The Esquire Almanac of Steak, his contribution being a feature called "Butcher," the memoir of his stint as butcher for Kincaid's Meats in Indianapolis, IN.He returned to writing for the magazine full-time in 2009.A periodic guest on radio talk shows around the world, Chiarella has made television appearances on "E: Hollywood True Story" and "The TV Guide 2011 Preview of the Oscars." In 2008, he worked as a consultant for NBC on the development of a television show based on his life, tentatively titled "It's Tom, in Indiana" (not picked up for pilot). They want to see a conversation in full, which never means a straight Q-and-A for me. And that usually extends beyond the experience of a single meal. They arrived as the second hand swept past the 12 at our appointed hour. Readers like a little ambiguity, a little progression of thought in their profiles. Same with Halle Berry, Charlize Theron, Ben Affleck. The presumption is that athletes and movie stars are always late, that they are sloppy with their time or their attention. He’s the only celebrity who ever held me up in this way.