Here’s a cute story that I’ll start with this New Yorker article of mine, “Café Luxembourg and the Art of the Restauraunt That Never Changes.”
In May of 2023, just a few months shy of 20 years of moving to New York City, I completed a checklist I started on a Greyhound bus ride from South Florida after that New Yorker article was published. In a notebook, I wrote down a list of publications I wanted to write for, from GQ to the New York Times to the Atlantic. By 2023, I’d written for all of them except for the one Harold Ross and Jane Grant founded in 1925. The New Yorker was my Moby-Dick. I just couldn’t figure out the right piece to try and pitch them so I didn’t…until I did. I wrote that article, it was one of the biggest thrills of my life, and then I got back to work because writing is what I do.
You know how in Goodfellas Henry Hill says “As far back as I can remember, I always wanted to be a gangster.” That’s me, but with writing. I don’t know what caused me to dedicate my life to figuring out how to string together sentences that people would actually want to read, but when I moved to New York City in 2003, my goal was to write. I had these grand romantic ideas about being like the Beats, Patti Smith, Jim Carroll, Lou Reed, Sam Shepard, Tom Wolfe, James Baldwin, the names I’d seen in the few copies of The Village Voice I’d been able to pick up on visits to the city, and basically anybody else I’d read who came from or ended up in New York City. That’s why it was such a thrill, in 2016, to write a long piece for Harpers Bazaar on Jay McInerney, Bret Easton Ellis, Tama Janowitz, Donna Tartt, and the rest of the “Literary Brat Pack,” all writers who helped color my idea of what being a writer in New York City once was. That was “Sex, Drugs, and Bestsellers: The Legend of the Literary Brat Pack.”
Of course, all the romantic notions of the writer’s life had been dashed pretty quickly when I started to understand the early-aughts NYC I was living in wasn’t the same affordable place it once was, and the media landscape was changing by the day. People were still unsure about the whole Internet thing, but it seemed that the lavish media and book parties I’d grown up dreaming of weren’t happening as much as they once had. So the first five or so years of what I could call a career mostly consisted of me working bartending and coffee shop jobs while hoping some magazine would let me write a 25-word blurb about a concert with free tickets as my payment. In 2008, after I started a small literary website with a dedicated audience, I started getting a little more work, but nothing to pay the bills. The way out of serving lattes and picking up barbacking shifts at sports bars to earn a few extra dollars was getting into editing, so I started a string of jobs at websites that were all doing great in the late-aughts and early-2010s, but by the middle of that decade, were either sold or shuttered. But I kept writing the whole time. Some of it was for the web, some for print. Some of it stank, and some of it I did because I needed a paycheck. But all of it was practice. I understand that now and I’m grateful. I thought a lot about that in 2022 when New York asked me if I had any thoughts on the Ukrainian community in New York City. I have family from there, but nothing I felt comfortable writing about. I did, however, spend countless hours in various East Village Ukrainian restaurants, reading, writing, editing, and of course, eating. Could I write about places like Veselka, B&H Dairy and some of the other great spots that are sadly long gone? That’s how “A Journey Down the Borscht River” happened.
Something I’m very proud of is that sometimes editors will reach out and tell me “I’ve got a Jason Diamond idea.” One of my favorite examples is from 2022 when an editor I love working with at Town & Country e-mailed to ask if I noticed prep school kids in Manhattan wearing gold chains. I said, “I know exactly what you’re talking about!” That’s how I ended up writing about the “Cugine Chain.”
This is one of those articles that looked better in the magazine because it comes with this shot David Schulze took of a few sandwiches from Defonte’s with some jewelry I wouldn’t mind rocking.
I don’t really consider myself a journalist. I say that because I have too much respect for journalists to say what I do is the same as what they do. I’m a writer and a cultural critic, but I definitely believe I’m influenced by journalists and the practice of journalism. One of the pieces I’m proudest of that also represents that influence is an essay that was in the 2024 issue of Esquire on “My Never-Ending Search for Adderall.” This was by no means hard-hitting journalism, but I do think it filled a void I noticed. The lack of drugs for people with ADHD was something that affected me and countless others, and I felt the reporting I’d seen on it was either pretty weak or just really boring. I wanted to do something that would get people’s attention on this and I felt that the best way to do that was to write something personal mixed with reportage. This piece blends my lifelong experience with ADHD and meds like Adderall, but also the underexplained shortage that had made it more difficult for people like me to acquire the drugs we’d been prescribed to help us function.
Talking with a celebrity is fun, but I especially love character actors. And I can’t think of anybody who epitomizes the modern character actor as well as Richard Kind. It was one of my dreams to write some sort of tribute to him, but then my editors at Vanity Fair let me take it a step further after I asked if I could do more of a profile. I’m proud of “Richard Kind Just Doesn’t Want to be Left Out” because Richard is a mensch, but he’s also talented and incredibly hard-working.
Another Vanity Fair piece I’m really proud of is my 2023 profile on the actress Amy Irving. I loved Amy in movies like Yentl and especially the rom com Crossing Delancey, and I wanted to see what she’d been up to since she doesn’t act as much as she once did. So we wat at Sweet Pickle Books on the Lower East Side and then when it was all done we crossed Delancey together. It was lovely.
I like to consider myself an appreciator of things, so when I’m allowed to write a tribute to something or a person I like, It’s one of my favorite things to do. In 2021, my editor at Esquire asked if I wanted to write anything about one of my personal heroes, Elliott Gould. I told my editor that I think Elliott is just as much a philosophy as he is an actor, and that’s how I ended up writing “The Philosophy of Elliott Gould.”
Sometimes I get to write criticism. In 2019 I wrote this piece for Poetry Magazine about a collection of poems, essays, and interviews all on Charles Bukowski and booze.
I also get to interview a lot of people. My 2024 interview with J.B. Smoove is a favorite of mine.
I interviewed Anthony Bourdain a few times, but my 2018 conversation for Men’s Journal with him is the only one I can find online.
I’ve also coined some phrases. People still talk to me about my 2021 article on “Bistro Vibes” for GQ.
Another thing I’m proud of is I get asked to write a lot of obits for people I respect. It’s not easy, because I attach so much of myself to the art and culture I love, but besides telling a person I appreciate them when they’re alive, I think being able to write a tribute to them after they’ve passed is the next best thing. One I’m proud of is Rolling Stone asked me to write about Philip Roth after he passed in 2018.
I also got to write a tribute to Norm Macdonald in 2021 for GQ.
And in 2024 I wrote about Richard Lewis, another comedian hero of mine who passed away.
I write about food a lot, but in no way do I consider myself a “food writer.” To me, it’s all about the experience. Like my 2018 New York Times Magazine “Letter of Recommendation” on bialys. It’s about bialys…but it’s also about making life easier for yourself.
I love writing about places, especially when a specific place connects back to a writer I love. In 2013, I wrote about Edith Wharton’s eye for design and tied it into walking through the part of Manhattan she grew up in for The Paris Review.
I’ve also written a few pieces about places connected to F. Scott Fitzgerald. One was also for The Paris Review, it was about the part of the Chicagoland area I’m from and Fitzgerald’s first love and muse, Ginevra King, lived. “Where Daisy Buchannan Lived” from 2012 is still a favorite piece of mine and got me thinking about other places connected to Fitzgerald. So a few years later I asked an editor at the New York Times if I could go to the Twin Cities and write about Fitzgerald’s hometown. That resulted in the 2016 piece “Tracing F. Scott Fitzgerald’s Minnesota Roots.”
I guess you could say I have a Fitzgerald trilogy because in 2022 I traveled to my old stomping grounds around Chicago’s North Shore and visited the house that Ginevra King grew up in, Fitzgerald visited and drew inspiration from, but had almost been leveled to make way for something new and ugly. Instead, new owners bought the property and have been restoring it to its former glory. You can read “The House That Inspired F. Scott Fitzgerald’s Daisy Buchanan Turns the Page” at Town & Country.
There’s plenty more you can find of mine floating around out there. Here are a few more I like.
I hung out with Iggy Pop in Miami in 2014. He wasn’t wearing a shirt. If he was then I assume the profile would be “I hung out with Iggy Pop and he had a shirt on.”
I profiled the director Taika Waititi in 2023. It’s a fun piece but I’m sad him telling me I have an incredible beard didn’t make the final cut.
In 2019 I feel like I wrote the piece on the true Chicago-style pizza for Bon Appetit. No, it’s not deep dish. But it is a deep dive into the history of tavern style pizza.
My 2019 Eater piece on bars and restaurants in the tri-state area with Sopranos cast members’ headshots is one of those things I probably did way too much for (driving three hours into New Jersey to eat at a red sauce place so I could confirm they had a signed pic of the guy who played Artie Bucco on the wall seems like overkill in retrospect), but I think it was worth it.
Even more “taking it a bit too far” was when I asked an editor at the New York Times to let me drive the entire state of Florida to show that, het, the Sunshine State isn’t that bad. I spent over a week driving all over the state for the 2017 travel essay “Finding My Florida,” and I love the piece, but I love that they illustrated me for it even more.
