It is nearly impossible to be a wunderkind for nearly 50 years, but somehow Adam Moss has pulled it off. It helps to look eternally youthful, but what does the trick for Moss is to be eternally curious, a trait that served him well as the founder of 7 Days, a weekly guide to the cool side of New York that lasted only two years yet managed to win a National Magazine Award shortly after its demise, in 1990. Moss would go on to collect so many more Ellies (named after the award itself, an elephant stabile by Alexander Calder) as the editor of New York magazine from 2004 to 2019 that he could have opened his own wildlife park (for the record, the herd would number 41).

His new book, The Work of Art, is Moss at his most curious and engaging as he interviews 43 artists about how they came to create a specific piece. Will it surprise you that the book itself is its own beautiful work of art, given the author’s famed eye for design and graphics? The Work of Art is seductive, enthralling, and a joy to read.

JIM KELLY: For those wondering what Adam Moss has been up to lately, well, I guess they know now! The Work of Art is a wondrous collection of smart people explaining how something—a painting, a piece of music, a novel—came to be. In that spirit of tracking an idea, what led you to writing the book?

ADAM MOSS: The short answer is, I left my magazine job and had the preposterous hope that I might be a painter, and when it turned out I just wasn’t good enough, I began to wonder if artists think differently than we mere mortals. So I began to ask painters and novelists and songwriters and joke writers et al. to take me through the making of a particular work—practically and psychologically—figuring the specificity of the task might reveal truths a more open-ended conversation might not.

But also (the longer answer), when I was struggling with painting I realized how drawn I was to evidence of artists “caught in the act of making art” (I’m quoting myself)—unfinished portraits, drafts, napkin doodles, and so on. I’ve always been really fascinated by process entrails, and as I began to see them everywhere I looked, I decided I’d build the book around them, as well, which really opened the project up for me. And then it morphed again as I tried to draw conclusions about what makes someone good at making art, and what the “work” of art is really about. The book is really a mash-up of book genres.

“When I was struggling with painting I realized how drawn I was to evidence of artists ‘caught in the act of making art.’”

J.K.: One of your case studies is about David Simon, creator of the TV series The Wire. Simon pivoted from a first season about drug rings to a much larger canvas about what ails American society, focusing in the second season on the Port of Baltimore and its longshoremen, and later on the education system and city hall. You write that for “work to be successful, it must match its moment in some way. Timing isn’t everything, but it’s a lot.” Are there one or two other examples among your case studies whose success depends so strongly on timing?

Pablo Schreiber and Chris Bauer in Season Two of The Wire.

A.M.: Well, also important for The Wire was the emergence of HBO, a medium that was made for the more ambitious television projects Simon wanted to make—and HBO was particularly attracted to noir-ish narratives of the sort Simon was built for.

But timing works in many ways. It shows up in Louise Glück’s poem “Song,” which was a COVID poem, about isolation and the power of imagination to get through it. So particularly about a particular time.

There’s a demented drag act Grady West devised around a character called Dina Martina which came out of the ironic-burlesque tradition that emerged during the AIDS epidemic in gay circles. Tony Kushner’s Angels in America also came out of that period, in its subject matter, of course, and its thematic preoccupations around the millennium, but it was also constructed around the needs that the Eureka Theatre Company, which commissioned it, had at that particular moment to give parts to its standing company—Tony built the play around the characteristics of the four actors he needed to develop roles for.

A spread from The Work of Art focusing on Tony Kushner’s Angels in America.

J.K.: Simon stresses how important it was for him to have a “bounce,” someone to argue with and ricochet ideas. Other artists you interviewed seemed to have no one to serve as “bounces,” and reading how George Saunders came to write Lincoln in the Bardo shows just how much he had to rely on arguing with himself. Were there traits that you detected in the loners, for lack of a better word, that made them different from those who have collaborators?

A.M.: One thing is, they talk to themselves a lot! They are their own “bounce.” I don’t mean talking to themselves literally (I mean, some do), but one of the things I noticed about these process artifacts is they were all ways artists have of conducting inner dialogues. One of the things I loved—you see it in a note Saunders writes to himself, also one that Michael Cunningham wrote as he was struggling through The Hours—is to see that inner dialogue actually rendered on the page pretty explicitly.

Also, artists tend to be very good at self-delusion—tricking themselves, especially by giving themselves all sorts of permission to fail so that they can extract material from their imagination in the early stages without too much inhibition. The painter Amy Sillman even allows for a stage (more than one) of painting over whatever she’d first made—she actually builds in a stage of destruction.

“I tried to draw conclusions about what makes someone good at making art, and what the ‘work’ of art is really about.”

The artist Amy Sillman and her floral still lifes.

J.K.: I learned so much from your conversation with Cheryl Pope, a Chicago visual artist who showed you many iterations of her work Mother and Child on a Blue Mat. Her art grew out of her painful miscarriages, and you actually preferred an earlier version done in felt. And she herself regretted showing the baby’s face in the finished painting. This illustrates a tension—“what to make explicit and what to make the viewer/reader work for,” in your words—that you saw present across mediums. What other works succeed in making the viewer or reader do most of the work?

A.M.: Both of the poets in the book—Glück and Marie Howe—talk quite a bit about subtraction—how the latter stages of a poem’s construction involve stripping the poem of its bridges so the reader makes his/her own leap. I mean, that’s what poetry does so well.

But it’s true across genres. Saunders talks about how deliberately he paced the beginning of Lincoln in the Bardo so the reader would feel at first confused, and then come to figure out the book’s rules, which would allow him to do all sorts of tricks later in the book. There’s a moment at the end of Sofia Coppola’s Lost in Translation when Bill Murray whispers something in Scarlett Johansson’s ear, which Coppola intended to fill in later but which she didn’t when she realized it was much stronger letting the viewer imagine what was being said.

Luring the reader/viewer to become a participant in the work by withholding exposition or clarity is an often very effective, even necessary, device. Of course, too much withholding and the reader/viewer gets so frustrated they just walk away. It’s a balance.

J.K.: The design of your book is integral to its success, with photos, drawings, manuscript pages all used to illustrate your points. And such great footnotes! The style of the book is captured succinctly in its first few pages: a black squiggle by Frank Gehry with the words HOW DOES THIS, then (turn page) BECOME THIS? printed over a full-color photo of his gleaming Guggenheim Museum Bilbao. How did your work as a magazine editor influence the book?

A.M.: I’ve just always been drawn to the ways words and images can be twinned to tell stories, and I’ve experimented with various ways to do this at every magazine job I ever had. Some of the experiments were a little berserk—I remember at New York a six-page, micro-type infographic of every plot switch in All My Children that we did when the show finally went off the air—editors and designers worked until dawn to finish. It was satisfying if inane.

And with print dwindling, I just wanted to see what could be done within the pages of a book—and with its abundant display of process artifacts that work like exhibits, I just wanted to see how far I could push it, and worked with my old fabulous design partner at New York, Luke Hayman, and his partners at the design firm Pentagram to integrate images with text as much as a book could stand while still being clear and engaging.

“Artists tend to be very good at self-delusion—tricking themselves, especially by giving themselves all sorts of permission to fail.”

J.K.: Reading your book, I tried to draw some universal lessons about creativity, but (and this is a compliment to the breadth of your examples!) I failed. What I came away with is how messy, random, and serendipitous the process can be, and the artists themselves are not always pleased with the result. Did anyone seem completely happy with the work discussed?

A.M.: Happy enough, yes. Completely happy, no, I don’t think so.

For one thing, every artist has to survive, as Michael Cunningham put it to me, the distance between what is in the mind and what he or she is able to create, and often that distance is vast. (One quality of really successful artists, I think, is that they are able to endure that chasm.)

But the bigger reason, and one that sort of stunned me, is how indifferent artists are to their final product. Sheila Heti wasn’t even sure whether How Should a Person Be? succeeded, and it’s considered a classic of early autofiction! The artists are relieved to get to the finish line, but often that’s it. What obsesses them, what gets them up in the morning and keeps them up at night, is the act of making art—the verb, not the noun.

J.K.: Good news! I am not going to ask you about the glory days of print magazines, the glory of which probably has as much to do with a nostalgia about one’s youth as it does about a paper product. I am curious about your news diet today.

A.M.: I still read a lot—still read the Times in print and all day in various digital forms, am glued to the Washington Post app, still love the magazines I loved (New York, The New Yorker, The Atlantic), read you guys enthusiastically, and get turned on to all sorts of stuff through social media (where I lurk but don’t engage). Also listen to podcasts, etc.—get news in ways that didn’t exist 20 years ago.

But, of course, I also read differently now, which is one of the benefits of moving on from my old jobs. I used to read defensively and opportunistically; now I read for pleasure (though horror, I suppose, is more often the case). And I entirely skip over big topics if I’m not interested (say, nope, will take a pass on yet another Speaker of the House coup, or Alex Murdaugh, or whatever). I’m aware of what media does to my psyche, which is often to fuck it up, and I am no longer obsessive about it. I’m pretty well informed but no longer a crazy person.

J.K.: Finally, the hobbies question! You were famously a workaholic editor, and obviously painting and reading and watching TV are relaxing. Are there other ways you unwind? Or are you happy just being a flâneur, the noblest of callings?

A.M.: I bike a lot. I play cards, am in a poker game, but the poker itself is the least of its pleasures. Love hanging with friends. I became a COVID cook but don’t really enjoy it. (So much work for so few minutes of eating? Obviously, I don’t get it.) Oh, I suppose I should admit to spending hours scrolling Instagram videos of people painting in sped-up motion—it’s my pornography.

Flâneur? Noble, yes, but not me in the slightest. When I left my magazine life, I fantasized being able to loaf. Alas, I am still my restless self.

Jim Kelly is the Books Editor at AIR MAIL