A Walk on the Upper West Side With Jason Diamond

"Honestly? I think all the things I write about are simply the things that I was intimidated by when I was a kid."

“Hey, you should buy this.”

Jason Diamond is holding an all-black cap with orange stitching that reads, “Zabar’s,” urging me to try it on. We’re in line at NYC’s legendary appetizing store—tagline: “New York is Zabar's... Zabar's is New York®”—on 2245 Broadway at 80th Street. Despite never being in the store before in my entire life, I take the hat from Jason and try it on. It looks good. Better than good, it looks great.

“Told you,” Diamond says, already knowing that I’m going to pay the cashier and keep the hat (at $13.00 it feels like a steal). It’s a quick moment, and I can tell Jason thinks nothing of it, but for me—well, it’s watching my friend do something that I deeply admire about him.

Jason Diamond is very, very, very good at recommending things. Or, to put it more elegantly, Jason has a keen eye for knowing what people will like. What they’re interested in. What will delight them, or at least put a smile on their face. It’s an excellent quality for anyone to have, especially a friend.

We’re walking on the Upper West Side during the tail end of summer because earlier in the day Jason texted me and asked if I wanted to go get a sandwich. Jason was right about this, too, because I did indeed want to ditch whatever I was working on and go eat a sandwich with him. When I asked him if I could turn our afternoon excursion into a Walk It Off, he happily obliged, texting back:

“In that case, let’s meet in Manhattan.”

Which is what we did, meeting somewhere south of Zabar’s in midtown and sweating our way toward the beloved New York City delicatessen.

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A sandwich on the Upper West Side, but not at Zabar’s.

Isaac: What are some of your favorite neighborhoods in New York City?

Jason Diamond: Sheepshead Bay. Brighton Beach. The Upper West Side. These are my New York City happy places.

I: Why?

JD: Well, I had family in Sheepshead Bay and Brighton Beach, and spent a lot of time there as a kid. Same with the Upper West Side. It’s all about my connection to these places. The Upper West Side especially captured my imagination when I was young. A certain kind of person lived here, you know? All the people that I respected lived on the Upper West Side—or the Upper East Side—in the ‘70s and the ‘80s. Before everyone started moving downtown. The Upper West Side was cosmopolitan. It was the epicenter of capital-N, capital-Y New York. When I aspired to be a New Yorker when I was young, I wanted to be the kind of New Yorker that you’d find on the Upper West Side.

I: Real quick, because you’re talking to someone who, when he first moved to New York, thought LES stood for Les Miserables. What’s the difference between the Upper West Side and Upper East side?

JD: One’s Jewish. One’s Gentile.

I: That’s it?

JD: That’s it.

I: Which is which?

JD: Upper West Side—the one we’re on—is the Jewish one. Upper East Side is—

I: Posh WASP?

JD: That’s were all the Gossip Girl shit happens.

All jokes aside, though, it’s nice over there. Some incredible shops and restaurants, but I’ve always felt more at home on the Upper West Side.

I: Was New York City a magical place for you growing up?

JD: In a way. It was a wonderful place to spend time. I wasn't born here. But you become a part of New York the more time you spend here. It’s one of the things I love about this city. Or maybe it’s more that New York becomes part of you. I think that’s more true for me. I didn’t become a part of New York so much as New York became a part of me.

I think that’s something very true about the immigrant experience. My father’s family was a family of immigrants. When you’re an immigrant, you’re simply trying to fit in—to blend—with the city, while at the same time maintaining your culture. Over time, you become a part of the city and the city becomes a part of you. So was New York City a magical place for me as a kid? Yeah. I remember. the smells, the noise, the color, the people. I remember being overwhelmed and in awe all at once. I had a dual citizenship, it felt like. Chicago and New York. Both of those places had such an effect on me.

But now I’ve lived in New York City longer than I’ve lived anywhere else. Longer than Chicago, where I was born. Longer than Miami, where my grandparents lived when I was a little kid. But I bring those other places up because—like New York—I think they have a very specific kind of connection to the past. These are cities that are always going through eras. So you get people who are obsessed with the way things used to be, saying, “New York City was cooler in the ‘70s.” Or, “Miami was really at its height in the ‘80s.” Now, of course, all these cities have changed in a myriad of ways—

I: Cities are living and breathing things.

JD: Right. And there’s this assumption that it was always better in the past. I remember thinking that when I was younger. “Oh, I wish I was here in New York during this era, or that era.” But now, there are kids who are asking me, “What was it like in 2002?” Which is so great, because you realize it’s always simply changing.

I: “It was the best of times, it was the worst of times...”

JD: There’s always going to be the New York City Dream versus the New York City Reality. But they’re both pretty great. I’ve been thinking about this a lot in terms of t-shirts.

I: I’m sorry, in terms of what now?

JD: There are all these punk t-shirts and show t-shirts and other weird t-shirts I had growing up that I didn’t think twice about, and now they’re selling at vintage shops for like $200 a pop.

I: Nostalgia for an era. Speaking of which, we’re coming up on Zabar’s. I’ve never actually been here before. What does Zabar’s mean to you?

JD: You’ve never been here before? My friend, I’ve failed you.

Growing up, when the adults around me would mention Zabar’s, I’d imagine a mythical city—somewhere deep in the desert. I had a whole story in my head written about Zabar’s before I ever even came here. I’d hear adults whisper, “Oh, they got this spread from Zabar’s.” Or, “We got these cookies from Zabar’s.” It was almost certainly the first brand recognition—that wasn’t, say, Coca Cola or McDonald’s—I had growing up. I remember wondering, “What is Zabar’s? Where is Zabar’s?” All I knew was that if something was good, it was almost certainly from Zabar’s.

Then I got to visit. I became immediately obsessed. I remember walking in and just—it’s all so beautiful. Come on. You’ll see.

I: So tell me about your connection to New York City. I remember you taking me down to Sheepshead Bay a few summers back. Is that where you spent most of your time as a kid?

JD: Yeah. I grew up with a lot of Soviet Jews in Chicago, too. In general, I’ve spent a lot of time in places with large groups of immigrants. Immigrants and old people. As a kid, I remember visiting neighbors who were Greek, neighbors who were Indian, and so on. I was exposed to food from all around the world at such an early age, and I’m grateful for that. It’s cliché to say food brings people together, but food brings people together, and that’s something I learned very early on in life—and it’s still such an important part of my life.

I: Hence you bringing me to so many of my most memorable meals over the years. It’s clear that you love bringing people together over food. During the pandemic, was that difficult for you—losing restaurants?

JD: How do you mean?

I: 2020 was difficult for all of us in so many different ways—and I don’t want to make light of that—but, as someone who clearly loves food, loves communion through food, loves restaurants and going out, was lockdown difficult for you?

JD: Yes. Restaurants. Stores. Bodegas. Sandwich shops. All these places being shut down—I hated it. I mean, we all did!

I: Are you so thrilled now that things are back up and running again?

JD: Eating out with friends is my greatest happiness. I’ll call you up, “Hey, Isaac. Wanna go get a sandwich?” I’ll take my wife out—

I: “Date Night in America.”

JD: Date night in America. I love going out and I love eating with people I love—or strangers. I love meeting new people. Food also gives me a reason to go exploring. I’m the guy that’s going to drive miles and miles into New Jersey simply to try a new mustard pizza I’ve heard about. And I’ll call some friends, “Hey, anyone wanna come try this new pizza with me?” That’s my whole life. So am I happy to have my life back? Yes. I’m happy to have my life back.

I: Is it safe to say part of your New York City Dream™ was being a writer?

JD: Yeah, absolutely.

I: Would you say you're getting to a place where you feel like you know where you're going? What you’re doing, as it were? As a writer, I mean.

JD: I’ve been working at this for about 20 years. I’ve been a professional writer—or editor in some capacity—for the last ten or so. I received my first real paycheck a decade ago. I grew up with this idea that writers write, and that's their job. That's all they do. Then the reality sets in where you realize, that's not necessarily how it goes.

I: So many writers we love had day jobs. Frank O'Hara worked at the Museum of Modern Art. Kafka was an insurance clerk. Toni Morrison was an editor at Random House. William Carlos Williams was a physician—

JD: Or even today—they’re tenured professors, or have some other mode of income. They work full-time at a magazine, or the New York Times. Whatever they have to do that allows them to write. So that’s where I am. I love that I get to write, so I’m trying to protect that. So every day, despite doing it for as long as I’ve been doing it, I wake up and say to to myself, “Ok, how do I keep this going? How do I keep being a writer?”

Because when I was young I figured, “I just have to write books.” But that’s not enough. I need to figure out how to do a lot of other things.

I: Spinning plates to keep income coming in.

JD: Maybe it’s podcasts. Maybe it’s screenplays. Maybe it’s editing. But it’s all of these jobs tangentially connected to writing—but at the core is the writing. I write every day. I know my writing improves because of it. Everything else is in service of the writing. I have to keep myself engaged. Keep working. Because for me—and maybe for all of us as humans—once you start kind of taking it easy, it's really hard to get back into always, always going for it. Constantly striving. So that’s where I am as a writer. I simply want to keep writing and do whatever it takes to keep doing that.

I: When you were just getting started, did you have an idea of how you would capital-B Become a writer? Any sort of roadmap?

JD: I knew it wasn’t straight forward. I knew that. I knew you didn’t, you know, walk into the office of the New Yorker or Vanity Fair, show them your college degree—which I didn’t have—and then they gave you a job. I wasn’t that naive. I knew at least that much.

But I also didn’t now how it worked. So I wanted to figure that out. I’ve always been that way. If I’m unfamiliar with something, I want to work and work until I understand what makes that thing tick. So I said to myself, “Well, I’m gonna do what I’ve always done, which is learn from the bottom up.” I set out to learn everything I could about the publishing world and the media world—starting with figuring out that they were actually two different worlds, which I didn’t know at the time. So that’s what I did. I knew I wanted to be a writer. It seemed like a lot of writers lived in New York. So I moved to New York.

I: You were in your early 20s, yeah?

JD: I was living in Florida. I was burnt out. I’d had a rough few years. Being burnt out at any age isn’t fun, but at 19 it can feel a particular kind of crushing. So I was having a really rough time. So I said, “Fuck it.” I got a Greyhound ticket and rode a bus all the way to New York.

I remember crashing with friends when I got here, and all of us getting really, really drunk that night. But the next day I woke up—miraculously without a hangover—and I walked out into the city. I remember the sun being extremely bright that day. I’d been coming to New York at least twice a year for most of my life, so I was familiar with the city. But it’s so big, there’s so much going on. It all felt very new. So I went out to explore it, and in a way, that’s what I’ve been doing ever since.

I bought the hat.

I: Do you remember your first writing gig?

JD: There was a punk magazine. It was in print, you could pick it up at Virgin Records and places like that. I’m trying to remember the name. But a friend asked me, “Hey, do you want to write about this band?” And I said yes. So that’s where I got my start, writing up shows and little record reviews that were 500 words—or more like 100 words—a pop. That lead to me doing small write-ups for Time Out New York, which then lead to my first time on a masthead, for this Jewish pop culture magazine called Heeb.

I: You’re gonna hate this, but humor me. Could you list all the places you wrote for and/or worked at over the last 20 years?

JD: Ok, so I already said Time Out New York and Heeb. Let’s see. Jewcy.com, The Rumpus, Faster Times, Flavorpill, Flavorwire, eMusic. A lot of internet work for all sorts of different websites, really. Including Volume 1 Brooklyn, which is a website I helped start. Eventually that all lead to a job at Men's Journal, which lead to a job at Rolling Stone. Then I worked at Punch, and then InsideHook. But at that point my writing starts getting accepted at places like the New York Times and New York Times Magazine, Paris Review, Details, Esquire, Eater, New York Magazine, Curbed, Vulture, the Wall Street Journal, New Republic, Bookforum, GQ, Vanity Fair. I mean, that’s off the top of my head. An easier way to put it is that I’ve pretty much published everywhere save the New Yorker.

I: Would that feel like a get for you? To write a piece for the New Yorker?

JD: Absolutely.

[Editor’s note: It feels rather lovely to share that Jason—at the time of publication—has now published a piece at the New Yorker.]

I: How would describe the writing you do? Culture writing? Or let me put it another way, how do you choose the subjects you want to write about?

JD: Honestly? I think all the things I write about are simply the things that I was intimidated by when I was a kid. I grew up loving clothes. Loving books. Loving food. But I didn't know how to talk to other people about these things—or I would be scared to share my opinions. You know, I come from a generation where there were still so many gatekeepers. People saying, “This is bad. This is bad. This is bad. This is fine, I guess. This is bad.” They judged you so harshly for your taste. “If you like this, you’re bad.” It was very limiting.

I never want to do that with my writing, but I do enjoy guiding people. Recommending things. One of my favorite things about New York City is everyone looks interesting. There are so many cool people in this city. But there’s a difference between looking interesting and looking stylish. To be stylish, you have to put a little thought into it. You can’t just pop something on—well, ok. Some people can. Peak Robert Redford or Paul Newman, for example.

I: Some people are gonna look sorta cool no matter what they’re wearing. Pete Davidson comes to mind.

JD: Well, that’s a style unto itself. But what I’m trying to say is I enjoy style when it’s clear that people have put effort into what they’re wearing. When they put a little thought into it—and then what I like to do is tell the story behind that thoughtfulness. Style for me is how you present yourself to the world, and that’s always interesting to me. How do people want to be seen? How do people want to be perceived?

I: Are you interested in the style of the moment? What’s fashionable?

JD: Yes. Because I’m always going to be interested in what’s popping off, because I’m always going to be interested in the story behind why it’s popping off. That’s always going to be fascinating to me. That’s always going to be something that I want to explore.

I: Sorta like what you were saying earlier, you’re a bit obsessed with what makes things work. You like to understand things.

JD: Exactly. But also, sometimes things just work, like this kid. That’s dope.

[Editor’s note: Jason points to a young person riding a skateboard down the street in that effortless manner that does indeed look plain cool.]

I: You mentioned spending time in numerous immigrant households when you were growing up. Do you think that in any way affected or inspired your interest in fashion?

JD: Oh, absolutely. 100%. Part of it was all the older people that I was surrounded by. I’ve always gravitated toward older people, my entire life. As a kid, I was constantly left in the care of my grandparents. They basically raised me. So I’ve always had a lot of older people in my life. The thought they put into their clothes—again, in the way that they presented themselves to the world—that always fascinated me. And yes, definitely—especially as I myself grow older—I’ve always been inspired by the care that older people put into the way they look.

Especially the way—and this is where the immigrant part comes in—the way that people highlight their culture in the way that they dress, or even in the way they act. I remember when my grandfather would have his buddies come around, and their conversations would be peppered thick with Yiddish phrases and sayings. They’d all have nicknames for one another. They worked hard and wanted to enjoy life, I always admired that.

[Editor’s note: At this point Jason takes a moment to help an elderly woman flag down a bus like we’re in some kind of Nora Ephron movie.]

To be honest, do you remember me saying that I feel at home on the Upper West Side? That’s part of it, for sure. I feel very at home when I come up here, and part of that is all the older people who live here, and all of the immigrants who live up here. People seem to take their time around here. Like look at that woman, checking those melons. I could watch people check melons all day.

I: Squeezing them and flicking them—

JD: Really taking her time. Life moves at a slower pace up here, and and I’m trying to learn how to do that. Take my time. Move at a slower pace. Plus, the fashion is incredible.

This is not Zabar’s, but at the is point the aesthetic of the Upper West Side has me in its grip.

I: Speaking of fashion—and in a way, I guess, older people appreciation—let’s talk about your Instagram. You have an incredibly curated vibe—for lack of a better word—happening over there. What do you enjoy about Instagram?

JD: When I was a young kid—and this was very much my dorky-kid-with-no-friends era—

I: Not to be confused with your oft under-appreciated Jason-as-a-jock-hockey-player era.

JD: Yeah. But back when I was little I would go to the library and take books off the shelves—or magazines off the magazine racks—and read through them looking for anything that I liked. I would rip through these books. One after another after another. Some books I’d go back to because I loved them so much. All different types of books. But really, it was a way to keep my mind busy—of keeping myself engaged with the world. Or maybe a better way of saying it would be, of making myself feel like I was engaged with the world, despite being so lonely.

Now, as an adult, I think I’m doing the same thing, in a way. But I get to share those things with other people—either on Instagram or via my Substack or Twitter—and what I love about it is how people now share things with me. All day I’m getting DMed cool old magazine ads, or book recommendations—

I: I text you a photo of every rad looking car I come across while I’m out walking.

JD: I love that! That feels good to me. It’s a fun way to stay engaged and interact with people, “Hey, look at this. Isn’t this neat?” My mind is always going, so it’s a nice way to stay busy—sorta in the background—while I’m working on an assignment or writing project. I don’t like quiet. Wait, that’s not quite true. I like purposeful quiet. I’ve been meditating for four or so years now. So I’m getting better at being still, and seeking out quiet. But when my gears are turning—

I: When your brain is bouncing—

JD: I embrace it. And I really like feeling connected to people through all of these different avenues. “Hey, check this out. This is cool.”

I: That makes sense. For me, I use Instagram as a sort of photo album. “I want to remember this moment.” For you, it’s not influencing per se—

JD: Yeah, no. I have no interest in being an influencer. It’s really me sharing anything and everything I come across that sparks my interest. Same as when I was a kid in the library, except now I get to share it with people.

I: Welcome to Jason’s World—or better yet, Welcome to Jason’s Brain.

JD: I love coming across something and feeling, “Oh yeah, baby! We're gonna post this.” I want my friends to experience things with me. I like people. I like spending time with people and I like sharing things with people. I love having people around, people to talk to, to share food with. Despite everything that I’ve seen and experienced in this world, I’m still in love with people.

I: So we were talking earlier about how New York City as a concept can be this sort of ever-changing dream. I feel like writing is that way, too. But here you are, publishing in all these places that you grew up reading. You’ve had books come out. How does reality stack up against the dream? Do you ever feel a bit like the dog who caught the car? How are you feeling?

JD: Everything I’m doing is my dream—and not just writing. I’m happily married to an amazing woman. The two of us live in an apartment that I adore, with my own office where I can work, which is work that I enjoy. I love the neighborhood we live in. I love my friends—my friends give me a real sense of family. I know how it sounds, but I really do feel like Ted Danson at the end of Cheers, “I’m the luckiest son of a bitch on Earth.”

I: Wiping your hand across the bar—

JD: Exactly. Now, that doesn’t mean writing isn’t a grind sometimes—I try really hard not to get burned out. Not to over do it. For instance, I had a pitch get shot down earlier today. But that’s part of the job. Is it disappointing at times? Of course. But I simply feel lucky that I get to do it at all. Even listing all those places that I’ve written for, it’s a weird feeling. Because I still feel in my gut how I felt when I first started out, “How do I get to keep writing?”

I: You’re always hustling.

JD: To be honest, that’s my problem. Like I said, that’s why I like coming up here to the Upper West Side. I’m trying to figure out how to slow down.

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Time passes. It’s a Saturday in September, and there’s news that Jimmy Buffett died peacefully in the night the day before—surrounded by “his family, friends, music, and dogs.” Not a bad way to go.

Jason calls me up and asks if I’d be interested in grilling a few cheeseburgers in celebration of the seafaring songwriter’s memory. Maybe drink a cold margarita or two. It’s a kind gesture, and one I happily take him up on, meeting on his roof deck to spend the night sipping cocktails and swapping tales with him, his wife Emily, and their wonderful dog, Max. I never would’ve thought to put something like this together myself, but I’m grateful to have a friend like Jason, who does exactly that.

Jason and his wife, Emily.