It doesn’t take a psychologist to see that The New Yorker’s imagery, its covers and ads, depicted the world like grandparents wanted to live in, the people they wanted to be.

Todd Pruzan

Todd Pruzan:
Was the golden age of The New Yorker cover the era when I was growing up, when the magazine and I were both learning vaguely to be Jewish?

Debbie Millman:
2025, in spite of all its problems, is turning out to be a good year for anniversaries. This, for example, is the 20th anniversary of Design Matters, 20 years of conversations with hundreds of the most creative people in the world from a huge range of disciplines.

Over those 20 years and especially in recent years, I’ve had conversations with a good number of contributors to The New Yorker magazine, cartoonist Roz Chast; cover artists Adrian Tomine and Christoph Niemann; fiction writers Min Jin Lee, A.M. Homes, Celeste Ng, Carmen Maria Machado; former New Yorker fact-checker and now frequent contributor Alexandra Horowitz; staff writers Susan Orlean and Malcolm Gladwell; even The New Yorker’s editor-in-chief, David Remnick, who I interviewed last year at the On-Air Festival.

This year is The New Yorker’s 100th anniversary, and I think it’s safe to say that the magazine has had and continues to have a huge effect on American culture, and on Design Matters, and on me personally. I’ve been a close reader of the magazine since the 1980s and I find it hard to imagine a world without The New Yorker showing up in my mailbox every week.

I’m a big fan, but for some people The New Yorker is a serious preoccupation, if not an obsession, such as the case from my friend and former colleague, Todd Pruzan. Todd’s a writer, an editor, a journalist, and an ad man. About 20 years ago, Todd was the managing editor of PRINT Magazine where I first got to work with him and I even had him on the podcast when Design Matters was in its infancy.

Todd recently got his hands on a collection of several thousand New Yorker covers. The collection had been with his family for the past 77 years and was recently passed down to him. The New Yorker had been a pillar in his family’s life and going through the covers led him to reconsider a number of things including his family’s and his own Jewish identity.

He’s written an essay about it and that’s what we’re going to hear on this week’s episode. That’s right, it’s been 20 years and for the first time, we are breaking format. You’re not going to hear a conversation. I’m leaving the room so you can hear Todd’s monologue about his family’s relationship with this now 100-year-old magazine.

So sit back, relax, and adjust your brain accordingly. Todd begins by describing a New Yorker cover from almost 80 years ago.

Todd Pruzan:
This is how it started.

In a kids’ bedroom, where a bunch of cheerful cartoon animals are frolicking on the sea-green wallpaper, two boys are sitting in a top bunk. They’re wide awake and pissed off. One is peering over the rail, glaring down at the bottom bed, where a bald man lies asleep and oblivious: banished, maybe, to snore off some after-work festivities. His suit jacket and striped tie drape off a hanger on the bedpost. And that’s how my grandmother finds them.

It’s a winter Saturday on a gentleman’s farm in Vienna, Virginia, a few winding roads west of Washington, D.C., and my grandmother is leafing through the day’s mail when she comes across that week’s issue of The New Yorker, dated January 17th, 1948. These two brothers and their unconscious dad are on the cover. The artist, Whitney Darrow Jr., has sketched this scene in bold pastel lines and exaggerated expressions. Obviously, he’s playing for laughs. As with a lot of New Yorker gags, Darrow serves us neither setup nor punchline: just the moment itself. He trusts his visual joke will stick the landing on its own. These cartoons don’t translate easily. You just had to be there.

My grandmother was there. Maybe she saw that cover the way I see it today: as a wink at Norman Rockwell’s gentle Saturday Evening Post Americana. It goes without saying that, by cultural default, this is a scene from a boys’ life, and these boys are as white as a new Frigidaire. Something about this bunkbed-slash-drunk-bed cover must have made her laugh, because she saved it. Not the whole issue, just the cover.

A few weeks later, she saved another New Yorker cover. This one, by Perry Barlow, features an older gent puffing on a pipe, tying fishing flies in tranquil bliss. Then another: an Ilonka Karasz illustration superimposing a floral Easter hat on the Aries constellation. Then another, by Rea Irvin, the magazine’s founding art director: a panicked child in PJs, running through a circus nightmare.

My grandmother saved thousands of these covers. A few of them, she set aside to make collages. The rest accumulated steadily for decades. Her collection migrated with her family, meaning my grandfather, my aunt, and my mom. It crossed the Potomac River from Virginia when they moved to Massachusetts Avenue on Embassy Row. Then, over to New Mexico Avenue, near American University. Then, across the D.C. line to the Maryland house where I grew up. And finally, to my parents’ home in the suburb I’d always called Rockville, but which the ever-inventive real-estate market has methodically and strategically upscaled as “North Bethesda.” These days, in North Bethesda, my mom is 81, and my dad is closing in on 88. And the covers still keep rolling in every week on an endless tide.

I was in North Bethesda for Thanksgiving two years ago when my dad waved me into his office to show me the covers collection. I’d known about it, but I’d never seen it. It didn’t look like much: two half-disintegrating cardboard boxes, groaning under the unbearable lightness of what I eventually determined to be 3,957 New Yorker covers. My dad, with his balance fragile after a few falls, really, emphatically should not have been moving them around. I don’t know how he got them into his office, and I didn’t ask. But with little fanfare, just a nonchalant, unceremonious shrug and a smile, he handed off the collection to the next generation.

I didn’t dare peek inside. I know myself well enough to know I’d be there all day if I took so much as a glance. Instead, I set the boxes in my car and drove a few hours home. I waited another day to lift the flaps. I knew this rabbit hole would run deep.

If I said I’ve come to think of The New Yorker as a proxy for our Jewish presence and practice, for prayer, for Hebrew school—maybe even for Judaism itself—would you think I’m out of my mind?

Now, I’m a New Yorker fan basically from birth, and I’ve always paid as much attention to its illustration and design as its writing. And their influence on me…well, you’ve heard this story before. But what if I said I’m now looking at the magazine as a cornerstone of my family history? What if I said that while my family downplayed our Jewish identity, The New Yorker became something like an article of faith? If I said I’ve come to think of The New Yorker as a proxy for our Jewish presence and practice, for prayer, for Hebrew school—maybe even for Judaism itself—would you think I’m out of my mind?

Hear me out.

“Do you have trouble letting go of old copies of The New Yorker? Blame the covers.” John Updike wrote that in 1989, in a lyrical foreword to The Complete Book of Covers from The New Yorker, and it hints at what’s behind this strain of obsessive, possessive bibliomania. Why is it that you can find New Yorker covers in used bookstores and on eBay that are 60, 70, 100 years old? Why do you find them framed in beach houses or glued up as wallpaper in rec rooms? Why do we have trouble letting go? Updike defined The New Yorker cover—he wrote: “It is the massive microcosm of Gotham, finding always something new to observe and, you could say, much to ignore.”

“Much to ignore”: I give Updike props for that. He didn’t need to notice, cloistered as he was in the wealthy, WASP-y fantasy playground of The New Yorker’s roots. I’m not knocking the magazine’s founding editor, Harold Ross, for snooty exclusivity. Nor do I fault Rea Irvin, whose original 1925 logo still runs on the cover every week, and whose foppish, haughty, heavy-lidded mascot, Eustace Tilley, or some version of him, still appears once a year, inspecting a pink spotted butterfly through his monocle.

The monocle and the butterfly: they made such a great metaphor for the magazine’s approach, studying life’s amusing trifles without noticing the city changing around it. In 1925, New York City was more than 95% white: a percentage that started plummeting in the 1970s and hasn’t stopped. When the magazine launched, fewer than 2% of New Yorkers were Black; today, Black people make up 20% of the city’s population. And the magazine sees the city’s 1 million Jews more fully now than it did in 1950, when twice as many Jews lived here.

Today’s New Yorker now looks assertively inclusive. It celebrates and satirizes a metropolis in full. It sees New York as the kaleidoscope world it is: hip-hop, hipsters, Hasidim. And the covers comment directly on our ephemeral, breakneck news cycle, whether through subtle imagery or gross caricature. If you can’t remember what Donald Trump was up to last week, it’ll probably show up on a cover by Barry Blitt.

That type of editorializing on the cover started just a few decades ago. Under Harold Ross and his successor, William Shawn, The New Yorker’s covers generally steered clear of the news. The Depression, the Holocaust, concentration camps, atom bombs: those early covers transported readers away from all things impolitic and impolite. Like diplomatic dinner hosts, they interrupted the difficult conversations and smoothly changed the subject. The first cover after the assassination of Martin Luther King Jr. was a soft-focus, foggy, rainy-day Victorian street scene by Laura Jean Allen. After Nixon’s resignation, the cover was a still life of an interior by Gretchen Dow Simpson. Even when Harold Ross gave John Hersey the entire issue of August 31st, 1946, to document the devastation of Hiroshima, the cover was a playful pastoral of Central Park that concealed the horrific reporting inside.

So I wonder what it was like for my grandmother to find that Whitney Darrow cover in the mail, with the two white-bread kids and their drunk dad. What could that picture mean to her? What could it mean to any Jewish subscriber? Could she feel it erasing her presence? And in that era of optimism and tension, did the erasure of her Jewish family from its field of vision soothe her? Did it sting her? Maybe a bit of both?

I spent two months sorting, scanning, staring, cataloguing the covers, miraculously unfaded by the decades, each as unique and tactile as a color Polaroid or a handwritten letter.

Inside the cardboard boxes, I found the covers filed sort of chronologically, in stiff pale blue and green manila folders, and also in heaping drifts. I spent two months sorting, scanning, staring, cataloguing everything in a kind of autistic frenzy, both the covers and the fascinating ads on the back, miraculously unfaded by the decades. Each is as unique and tactile as a color Polaroid or a handwritten letter, and feels just as personal. Each bears its own life lines, its own folds and tears along the binding. The covers from 1952 to 1964 are bisected with hairline scores down the center, when the post office apparently creased them that way. The magazine’s current publisher, Condé Nast, spent 20 years in the 1990s and early 2000s vandalizing the covers with barbaric glued-on mailing labels, and these covers bear the scars. The August 7th, 1965, cover has a phone number someone in my family had penciled across an empty sky. (289-7148, in case anyone still needs it.)

I wasn’t sure what to do with this archive. I started an Instagram account, posting one cover every day on the anniversary of its cover date, plus the advertisement on the back of it. But as I did, I realized I was also piecing together a sort of alternate family history, time-stamping moments in our lives. A pink tree blossoming in front of a red barn: that was the cover the week my parents got married. A detail of cables and wires on a suspension bridge: my college graduation. A bike messenger bearing down on a Tour de France peloton: I got married. Joyriders on a roller coaster pulling into a subway stop: the birth of my daughter. A dog leaning out a window to witness a parade of American flags: the birth of my son.

I took copious notes, revealing a satirical gaze on wealthy white society: meditative, humorous, slapstick, surreal, actively denying the changing city in a turbulent world. I tallied 30 covers depicting cruise ships, 29 with sailboats, four with yachts, two with marinas. Twenty-one covers are about golf, 20 about skiing, 11 about tennis. Thirty-three show horseback riding, horse racing, horses pulling carriages. Thirty feature businessmen—specifically, men. Seventeen have maids and five have chauffeurs. Seventeen take place in art galleries, 10 at cocktail parties, 21 at the pool.

Plus, there was all that advertising. So sumptuous, so pompous in its self-regard, so florid in its poetic prose. It’s all just so…written. Sedans! Suits! Perfumes and face powders! Air lines and sea cruises! Scotch whisky, Canadian whiskey, Kentucky bourbon, London dry gin, cognac, Champagne, crème de menthe, Dubonnet, Campari, Dewar’s profiles, Absolut perfection—my God, did these readers love drinking.

And just as Updike saw, something obvious was missing. Everyone on these mid-century New Yorker covers and in the Mad Men ads represented a tight-knit club, however comical: a C-suite caste where Black people, people of color, and Jewish people did not belong or even, for the most part, exist.

But let’s begin again, at the beginning. My beginning this time.

A psychedelic cat-headed human blankly contemplates two apples and three pears in an open cabinet shaped, for whatever free-associative reason, like the number 5. That’s the cover of The New Yorker the week my twin brother, Jeff, and I were born, on a summer afternoon in D.C., under the auspicious sign of Saul Steinberg. When I found Steinberg’s cover in the collection, I thought, yeah, that tracks.

We grew up in a small split-level in a new suburban neighborhood: mom, dad, brother, and younger sister, Tracy, born four years later. The cover that week: kids, toy sailboats, Central Park fountain. We had blue shag carpet and heavy ashtrays and lighters on a glass living-room coffee table, because it was the ’70s. And we had New Yorkers on most available surfaces.

If you’re imagining a house full of clenched jaws, highballs, white gloves, nine irons, you’re in the wrong house. My Dad’s ride was an Audi Fox, back when Audi was a cheapshit little rattling box from West Germany. Here’s the Audi ad on the back of the cover of the August 20th, 1973, issue. It says “8 cars. $4,385. The Audi: It’s a lot of cars for the money.” Yeah, right. Our Audi Fox literally fell apart at the seams, sloughing off its interior vinyl in flopping sheets.

We kids watched plenty of TV. We graduated from The Beatles to Friday Night Videos to used-record stores. A vintage pinball machine called Aztec rang and dinged with a racket way out of scale with a house that size. My brother and I played soccer pretty badly, usually on defense. We collected stamps, coins, baseball cards. We grew up in the vacuum between the Senators and the Nationals, so we rooted for the Orioles.

And man, did we have magazines. Down on the coffee table: Time, Life, TV Guide, Sports Illustrated, People, American Film. Upstairs in our rooms: Highlights, Cricket, National Geographic World, Dynamite, Boys’ Life, and later, at the height of our post–Dungeons & Dragons geekery, Omni. And hanging over the upright piano was my grandmother’s handmade collage of New Yorker covers from the late 1960s and early 1970s, probably 15 or 20 random covers overlaid at jaunty angles, with a Eustace Tilley cover positioned at the center, as though atop a pile.

I have no memory of a time before Eustace frowned down at us from that wall: forever turned in profile, where he could focus on his butterfly and ignore the rest of us.

I grew up literally looking up to The New Yorker: I have no memory of a time before Eustace frowned down at us from that wall. Yes, we had that poster of Saul Steinberg’s “View of the World from 9th Avenue”—the cover on March 29th, 1976—framed and hanging in our kitchen. But downstairs, we had Eustace, forever turned in profile, where he could focus on his butterfly and ignore the rest of us. I got to know the other artists: George Booth’s snarling dogs and grizzled owners; Gretchen Dow Simpson’s better homes and gardens; the creepy, kooky, mysterious and spooky, altogether ooky haunted mansions of Charles Addams. I must have wanted to be a New Yorker cartoonist, because I tried drawing weird single-panel gags that amused me but probably didn’t make much sense. I didn’t start reading it until later, although my dad at the dinner table occasionally read us Pauline Kael’s review of the movie we’d watched that afternoon. Most of it soared way over my head.

Still, all this writing and art, the magazine’s and my own, may have been my family’s way of having conversations, our way of practicing a faith. We had no mezuzah on our doorframe, no menorah on a bookshelf, no seder plate in a dining room cabinet display case. There were no discarded yarmulkes stuffed in our kitchen junk drawer. We had no Torah portions in study workbooks or on cassettes. We joined no congregation. We attended no Hebrew school and had no bar mitzvahs.

Like most Yiddish, farblondzhet means exactly what it sounds like it means. Roll your eyes and throw up your hands while you spit the word out, and there’s your definition.

We did have my dad’s old black prayer book, published in English and Hebrew, tucked away on a shelf in his study next to his monthly bridge digests. Drawing from his early years in Chicago’s South Shore neighborhood, my dad even handed down a trace of Yiddish. I still rely on farblondzhet, a word unmatchable in its versatility and its onomatopoeia. Like most Yiddish, farblondzhet means exactly what it sounds like it means. Roll your eyes and throw up your hands while you spit the word out, and there’s your definition.

The New Yorker had about as little to do with my dad’s childhood as his beloved White Sox had to do with the World Series. Just as his father had emigrated from Minsk 30 years earlier, my dad mapped his own course out of the old neighborhood. He stayed to get his University of Chicago Law degree, then headed east to the Department of Justice. It’s fair to say Washington, and my mom’s family, absorbed him more than the other way around. After a D.C. career measured in decades, he led tourist groups in retirement through the Library of Congress and the Supreme Court. He kept his South Side bona fides—he’s still White Sox ride-or-die—but he bonded with my mother’s mother on football, a mutually sadistic backgammon feud that played out in our kitchen, and The New Yorker. I don’t know when my Dad first got interested in it, but my archive includes two copies of almost every cover from 1971 to 1982.

My mom’s side was a different type of Jewish: bluer blood, assimilated for many generations. Recently, my mom sent me a 1951 clipping from the Washington Evening Star announcing the death of her great grandmother, whose own parents had arrived in town from the Schleswig-Holstein region sometime around 1832. My great-great-great-great grandfather on my mom’s side, Philip Peyser, had been a haberdasher, and the article suggested that John Wilkes Booth might have been wearing one of Peyser’s hats to Ford’s Theatre on a fateful night in 1865. I texted my mom back. I said: “I always figured the Jews had a hand in Lincoln’s assassination.”

My parents—and so my brother and sister and I—we were liberal-Jewish-American enough. We had Mel Brooks and Steven Spielberg and, for a while, anyway, Woody Allen. My parents had Barbra Streisand, Barry Manilow, Neil Diamond. My sister was an early adopter: she had the Beastie Boys. But for me, Jewish rock wasn’t really a thing, even though Billy Joel’s album Glass Houses was the first non-Beatles cassette I ever asked for. I was terrified of Kiss and its lead singer, Gene Simmons, born Chaim Witz in northern Israel. I didn’t like Rush, the prog-rock trio from Toronto, fronted by the Jewish-born Geddy Lee, mostly because I didn’t like the kids who liked Rush. One puzzle piece did click into place when I was 10 and heard “Blitzkrieg Bop” thundering out of someone’s very loud stereo. Something about the faux-British yelp of Joey Ramone—or Jeffrey Hyman, to his mother—made the air feel different. I could sense I was hearing a code getting cracked.

But one code I never did crack—I still haven’t—is how to be Jewish. My dad had grown up observant until, at some point, he wasn’t. And because my mom never had been, our household, Jewish on paper, was fully secular, untethered to faith. Until third grade, Jeff and I even attended an Episcopalian school, with morning chapel and the Lord’s Prayer and an elaborate Christmas pageant.

Like much of the conversation that went on and didn’t go on in our house, these magazine covers were more subtext than text. They did their talking without words. I can see precious little in this collection about being Jewish. And the more I studied these covers, the more I could see that absence from my upbringing.

It doesn’t take a psychologist to see that The New Yorker’s imagery, its covers and ads, depicted the world my grandparents wanted to live in, the people they wanted to be.

Our podcast bookmarks, our Netflix queues, our Spotify playlists—everything we listen to and read and watch embodies the way we see ourselves. The magazines around our house were the Instagram profiles of the day: curated feeds reflecting to any visitor, and to ourselves, the lives we wanted to live. It doesn’t take a psychologist to see that The New Yorker’s imagery, its covers and ads, depicted the world my grandparents wanted to live in, the people they wanted to be. I don’t remember how old I was when I finally figured out Eustace Tilley himself was a man, not an old lady. More than anyone else in my life, Eustace looked like my grandmother.

But every publication has to strike some balance of emphasis and erasure. If The New Yorker of the early decades had tried for full and accurate representation, it would’ve been a magazine about everything, which is to say, a magazine about nothing.

John Updike was of course no stranger to The New Yorker’s wealthy white world. But even as he saw the magazine reflecting and lampooning its genteel audience, he also chose to see what the magazine studiously avoided. In 1989, he wrote: “The population of the covers becomes one class, the prospering middle class, and one color, white.…A number of the covers…would certainly be considered unprintably racist now; yet there is something racist, too, about the virtually absolute postwar disappearance of black people from New Yorker covers.”

If The New Yorker of the early decades had tried for full and accurate representation, it would’ve been a magazine about everything, which is to say, a magazine about nothing.

Since Updike wrote those words, the magazine’s covers have done an about-face from that whitewash. Apart from its logo, which is virtually unchanged since he designed and hand-lettered it 100 years ago, Rea Irvin himself might not recognize his own magazine today.

That shift started in the early 1990s, when incoming editor Tina Brown and art editor Françoise Mouly updated The New Yorker with heat and spice, steering its visuals in explicitly topical, provocative, often news-making directions. Brown made her intentions clear from the start. The cover of her first issue, October 5th, 1992, featured Edward Sorel’s illustration of a prim Central Park carriage driver in top and tails, warily eyeing the pink-mohawked punk customer slouching in his back seat.

1992-10-05 | Edward Sorel | Central Park carriage driver with pink-mohawked punk as his passenger (first Tina Brown issue)

Art Spiegelman, author of Maus, and Mouly’s husband, soon made a notorious debut with his 1993 Valentine’s Day cover depicting a Hasid and a Black woman sharing a romantic kiss. Spiegelman’s image featured possibly the first unambiguously Jewish person ever to grace the magazine’s cover. It charmed some New Yorkers and offended others. Spiegelman had a gift for pissing people off. His 1999 cover responding to the NYPD’s brutal murder of Amadou Diallo, an unarmed 23-year-old Guinean student in the Bronx, sparked police protests: a fitting response for a metropolis personified in the 1990s by its wild-eyed mayor, Rudy Giuliani, whose default setting was always calibrated to sputtering, spittle-flecked rage. Today, it’s rare for a magazine cover to drive the news, or to capture and express our nation’s grief the way Spiegelman and Mouly did in 2001 with their haunting black-on-black portrait of the Twin Towers. But these New Yorker covers really did do those things.

Looking at thousands of covers at once accelerates and compresses the gradual shift from Ross’s timeless melody to David Remnick’s daily bread. Since Remnick took the editorial reins from Brown in 1998, he’s only turned up the news dial. But before Brown, many of the magazine’s cover illustrators erased parts of themselves. Abe Birnbaum painted still lifes in heavy brushstrokes. William Steig sketched an odd barbershop-quartet Americana. And Saul Steinberg was a head trip. These Jewish artists’ styles were distinct and personal, but they weren’t autobiographical, and they weren’t clearly Jewish.

Was I imagining this erasure? I called my old friend and colleague Steve Heller for a gut-check. Steve, who’s co-chair emeritus of the MFA Design program at the School of Visual Arts, might know more about graphic design and its intersection with Jewish culture than anyone alive. He saw the same thing I did. He said, “The publishing ilk of New York in the 1920s and ’30s were not embracing Jewish culture. The New Yorker filtered any New York Jewishness out of the covers. With so much anti-Semitism in the U.S. in the ’30s, before and during the war, it wasn’t really a plus for circulation to admit to any kind of Jewish culture. That was vaudeville,” Steve said. “Y’know: the dirty stuff.”

Okay, no surprise there. But there was something I did not ask Steve about: something I noticed more and more as I went spelunking through these thousands of covers. After decades of erasure, a change started bubbling up in the 1970s and 1980s, right when I was growing up, emerging slowly and subtly, like a photograph developing in a darkroom tray. The characters on the covers and in the cartoons, and the scenarios and environments they lived in—they were all starting to look a little more liberal, a little more Upper West Side, a little more Jewish.

Robert Mankoff, Arnie Levin, Roz Chast: their covers were droll, they were neurotic, they were New Yorker-y. They weren’t explicitly Jewish. But as the magazine was taking baby steps into Jewish humor, one artist may have tipped the scales.

Edward Koren’s characters might have been the first to look more like The New Yorker‘s readers than the snooty socialites of previous decades. I wondered if Koren, consciously or not, had been building a bridge between the magazine’s first half-century and the next.

Ever since I was a kid, one of my favorite New Yorker artists has been Edward Koren, whose happy, hairy, giant-schnozzed monsters seemed to send up the emerging enclave of bougie Manhattan hippies. And as I paged through 32 of his covers from 1971 to 2022, I realized his characters might have been the first to look more like The New Yorker‘s readers than the snooty socialites of previous decades. I wondered if Koren, consciously or not, had been easing the magazine into this new New York—if he was building a bridge between the first half-century and the next.

Koren died in 2023, at 87. I couldn’t ask him about my premise. But his daughter, Sasha, recently told me what she thought her father’s artistic intentions may have been. She said, “Although he was entirely secular, he was unmistakably a Jewish New Yorker—in his sense of humor, of course, but also in his appearance and the cadences of his speech, which was peppered with Yiddish words—and he would never deny his roots.” Sasha went on: “He was surely aware that portrayals of the culture of Upper West Siders of the ’70s to ’90s contained some aspect of secular Jewish culture. But I think he portrayed it because that’s what he saw and heard. Those people, sights, and turns of phrase are what interested or delighted or amused him.”

Shortly after our exchange, Sasha sent me an appreciation that ran in New York Jewish Week just after her father’s death. And the essay’s author, Andrew Silow-Carroll, had noticed the same thing I had. He wrote, “Many of Koren’s characters seemed Jewish even if he didn’t say so. And Koren…seemed never to have said so.” So Edward Koren really may have been that critical catalyst at the exact moment in The New Yorker’s history when the Jewish culture that amused him first rhymed with what amused its editors.

My conversation with Sasha Koren made me realize something else. Just as The New Yorker was gently leaning into a more Jewish direction, my family was doing pretty much the same thing. My mom had started volunteering at the local Jewish Community Center, where she made lifelong friends. And we all started spending more time there, after school and on weekends, getting exposure to Jewish culture in a very low-pressure setting. I could see the exposure was rubbing off on my parents, too, as they tried, a little noncommittally, to jumpstart a menorah-lighting tradition.

In retrospect, we may have reached our fork in the road on a long-forgotten Sunday afternoon when I was about 10. My parents had led us around the JCC while Hebrew school was in session. That could have been the start of a new chapter, a true embrace of Judaism. But then my parents made a grave strategic error. They asked us a question they never should have asked: Did we want to go to Hebrew school?

Let me get a little rabbinical here and answer that question with a question. What 10-year-old kid in their right mind leaps at the chance to go to even more school? On the weekend?

My parents didn’t press the issue. The moment passed, and that was pretty much that. We would remain in our liminal space of secular ambiguity, putting up a Christmas tree once a year, and maybe lighting menorah candles, too, if we remembered to do it.

Did my family break from Jewish tradition by design, by distraction, or by neglect? The answer sits somewhere in the middle of that Venn diagram of ambiguity, right there with my name. I’ve programmed myself over the years to spell “Pruzan” on first reference, and whenever someone asks me what Pruzan “is,” I explain: “It used to have a ‘-sky’ at the end.” My dad and uncle each dropped the suffix. I’ve never fully understood what they were trying to accomplish. My Dad’s explanation, that he was trying to make his name easier for others, never satisfied me. He recently told me he wonders now whether changing his name had hurt his father. I wish he’d asked.

But in an era of prevailing unmasked, microaggressive anti-Semitism—an era maybe a little like our own—that “-sky” might have been a professional liability. Introducing a little ethnic ambiguity, just enough, might have made him more employable. And the result does have its charms. Once, when I was a young editor at Chicago magazine, I called up Studs Terkel, who was then 84, to set up an interview, and he sassed me: “‘Pruzan,’ eh? Sounds like a pharmaceutical!” The other editors in our open-floor office swiveled their heads as I barked with laughter: my own name’s similarity to Prozac had somehow never crossed my mind. And then Terkel quickly said, “I’m just horsin’ around with ya.” I fell hopelessly in love.

My mom’s side made no such feint at camouflage. Now, I’m not going to tell you her maiden name, for the same reason I’m not telling you the name of my first pet, or my high school mascot, or my first concert. (Okay, fine: Duran Duran at the Capital Centre, Landover, Maryland, 1984.) The point is, my mom’s family name was not just plainly Jewish but, I have to assume, for a while during her childhood, wincingly problematic. I’m glad my grandparents didn’t change it, though they must have felt pressure to use it discreetly. Once in the ’50s, they went to a fancy party at a notoriously anti-Semitic country club—I won’t name it, because it still exists—but when they arrived, a greeter advised them not to use their surname. They walked out.

I learned pretty early on, through some unspoken cues, that the “-sky” that had once been in my family name was also an inheritance that needed some protection. Not a secret, exactly, but maybe not fully safe to bust out in front of complete strangers, either. Not even in our deeply Jewish suburb. Not even 40 years ago. And, I’m sad to say, maybe not even now.

Was the golden age of The New Yorker cover the era when I was growing up—when the magazine and I were both learning, vaguely, to be Jewish?

There’s no doubt Edward Koren and Saul Steinberg left their mark on me. But I think the golden age might be right now. This is no longer Eustace Tilley’s magazine, perched high above us. The New Yorker lives with us, in our world. And any issue that introduces itself each week through Kadir Nelson’s heart-stopping Black American portraits, or Christoph Niemann’s playful metaphors, or Chris Ware’s meticulous architectural drama, or Roz Chast’s eternal anxiety, is already an issue worth saving.

A year ago last January, my dad texted me. He said: “This week’s New Yorker cover should be a keeper.” He was talking about Barry Blitt’s latest insult of Donald Trump, goose-stepping across the page, back when the idea of a vengeful Trump returning from his rightful place in obscurity still seemed absurd: an unwanted sequel to the worst slasher movie ever made. I was so grateful to get this text, because it meant my dad was okay. He’d slipped a few days earlier while loading groceries and landed behind his car, smacking the back of his head on the parking-lot asphalt. He’s taken his share of spills before and since, but when my mom came back to the trunk and found him K.O.’d, she’d assumed the worst. Unbelievably, though, I was on the phone with him a couple hours later, after an ambulance ride and a check of his vitals. He was sheepish and shaken but in good spirits. He was lucky. I’ve been lucky, too: lucky that this was only the first time his mortality had seemed so immediate, so scary. And here he was, five days later, enjoying Barry Blitt’s New Yorker cover enough to tell me about it. And that was a small, good thing I could file away for safekeeping.

Here’s another small, good thing: I’m old enough that the books on my shelf are turning up on my kids’ syllabus. When I learned my daughter’s 12th-grade English class would be reading The God of Small Things, I couldn’t resist showing her my copy, a first edition signed to me by its author, Arundhati Roy. A few years ago, after her class had read Art Spiegelman’s Maus, my son, who was 10, found my copy and asked to read it. I handed him both volumes and discreetly emailed a heads-up to his teacher. “I know this is a comic book,” I told him, “but it’s not funny, and it might upset you, and we’re going to have to talk about it.” Now he’s 13, and he’s told me he might be ready to read it again.

Most parents try to pass along our favorite qualities and stop the cycles of anything we didn’t want to pass down. And as I’ve tried to transfer the right traits and stop the others, I’m realizing I may not have said enough. Maybe I’ve overcorrected. Maybe I’ve taken too much care not to impose my special interests onto my kids: my books, my music, my movies, my own writing, or, come to think of it, The New Yorker. I never wanted my kids to think of anything I love as a school assignment. They’ve noticed a few of my passions, like the books on my shelf. And they do hear Jewish rock, because sometimes, when we’re driving and I can’t decide what I want to listen to, I put on Yo La Tengo. But I’m proud to see these two blaze their own trails. New Yorker issues don’t stack up in piles around our house, but now I hang onto the covers.

What does faith look like for us? My wife grew up Catholic, more serious about her faith as a child than I’d ever been. That makes our kids half-Jewish but fully secular. They’re curious in ways we couldn’t have planned and wouldn’t have expected. Our son keeps the King James Version on his shelf, and we know he didn’t pick that up from either of us.

My own parents got more serious about Judaism once their kids were out of the house. Sometimes, I have regrets that I didn’t grow up with it, especially around the high holidays. But I love the traditions we’ve handed down, too, like that most secular of symbols: the Christmas tree.

Maybe your family did the same thing mine did, or does it right now: shunting aside that old-time religion for newer faiths to bond over, new worlds to explore together. Maybe faith in your household doesn’t look like The New Yorker. Maybe it looks like the Patriots or the Lakers. Maybe it’s Taylor Swift, Kendrick Lamar, Springsteen, Prince. Maybe it’s Harry Potter, Broadway, Minecraft, Disney World. Maybe it’s design.

There was a moment, early on in my life as a dad, when my parents gifted our family a menorah. I wasn’t sure what to do with that, and my parents were puzzled that I was puzzled. But Judaism was something we hadn’t talked about, or not directly, or not enough. I might have seized that moment to lead my own family in lighting the menorah. But I wouldn’t have been passing that tradition down. I would have needed to learn it myself. And to learn it myself, I’d need to go back, and begin at the beginning.

Debbie Millman:
Todd Pruzan, or dare I say Pruzansky. You can check out his collection of New Yorker covers on Instagram at @NewYorkerCovers365. This is the 20th year we’ve been podcasting Design Matters, and I’d like to thank you for listening. And remember, we can talk about making a difference, we can make a difference, or we can do both. I’m Debbie Millman and I look forward to talking with you again soon.