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So What Do You Do, Danny Gregory?

A former ad man turned freelance illustrator on changing careers, drawing the news, and the age-old task of turning tragedy into art.

By Chris Gage - June 8, 2004

Danny Gregory creates art that is surprising, beautiful, and articulate—art about common objects and how we see them, or, more often than not, how we completely fail to see them. "The reason most people draw badly," he says, "is because they draw symbols instead of what they see. A nose is a triangle. An eye is a circle with another inside. It's very human, assigning things to categories, using symbols and signs." In Gregory's work, there are no symbols to articulate a thought; instead, his pieces frequently incorporate words, a technique that gives the impression of thinking aloud—sparse, exact, and humorous words, as much a part of the picture's "pictureness" as the watercolors are.

This seamless merger of illustration and commentary is something that, no doubt, comes naturally to Gregory, who only recently left an executive job in advertising to freelance and concentrate on his own work. Since striking out on his own, his art has appeared in The New York Times, Print, and on the website The Morning News. He has published two stunning books, Everyday Matters—which recently received an honorable mention in The Comics Journal's 2003 Books of the Year—and Hello World: A Life in Ham Radio, and he has one book forthcoming: Change Your Underwear Twice a Week: Lessons from the Golden Age of Classroom Filmstrip.

While it's almost ridiculously futile to interview Gregory—between Everyday Matters and his website, he has explained and discussed his life and work in great detail, from the subway accident that left his wife paralyzed to his favorite type of pen—Gregory recently agreed to speak with about his two careers, how drawing can be a form of journalism, and what makes him a territorial bastard.

Birthdate: September 4
Hometown: London, England
First section of the Sunday Times: Book Review

In a long piece on your site called "Why Do I Do It: My Story," you briefly describe your transition from advertising to artistry by saying, "I let art back in the door and suddenly the walls started to crack. Within a month, I had a book contract. A few months later, I had a second, this one to publish my illustrated journals. Before long, I had an agent and was no longer a creative director." Can you give a less perfunctory version of the story?
The first book I wrote was for Princeton Architectural Press, and it came about quite by chance. I was at a book launch party, met my future editor, Jennifer Thompson, and told her about a collection of ham radio cards I just found at the flea market the previous weekend. She said they sounded interesting, suggested I come into the office to discuss them with her, and a few days later I had a book contract. It was all serendipity. When we were working on the book, I showed her some of my illustrated journals and soon Princeton had agreed to publish them as well. Having these books under my belt made it easier to convince a great agent to represent me. And with all this momentum, I felt more comfortable about stretching beyond my career in advertising and redefining myself.

After 20 years in advertising, you were pretty negative about your experiences there. Why do you think you were you so good at something you didn't seem to enjoy?
I'm not pessimistic about advertising. I think, to be honest, I was more unhappy with my reaction to the business. I allowed my job to take over a disproportionate amount of my time, energy, and dreams. That could have happened in another industry, too. My point in talking about my career is really to encourage other people not to feel trapped in what they're doing. I think it's important to diversify your life, to have a range of interests, and to find some way to truly express yourself. While advertising is a creative medium and allows one to use one's imagination, personally I didn't feel like my work was an adequate way to express who I am and how I see the world. My other projects give me much more of that sort of validation. Because doing advertising well is so all-consuming, I stepped down from my executive life to give myself a more varied diet.

In your current work, words seem as integral to the art as the drawing. Has this always been the case, or is that something you learned from your career in advertising?
I see myself as a writer more than I see myself as an artist. And, in my insecurity, it seems easier to be a better illustrator than most writers and a better writer than most illustrators. I also love calligraphy and see it is a pretty important part of look of the things I make. Calligraphy necessitates words of some sort, and, rather than using soppy quotes and poems, I make my own stuff up.

Your work is a quite romantic and whimsical—not something you normally see in a daily newspaper—and yet you've been published frequently in the Times. How did you start working with them?
Connie Rosenbloom is the editor of the City section of Times. She read my book, liked what I do, and contacted me. I showed her a couple of recent pages from my sketchbook: one about the fact that so many dogs in New York wear coats as soon as the temperature drops below 50, and another about the strange things one can buy on Canal Street. And she immediately sparked to them. She and the art director, John Cayea, have been very encouraging. Their section is less typical hard news and more an attempt to chronicle the life of New York. They tell me that I'm able to cover stories in a way that wouldn't be as successful purely in words.

What do you think of the way art is handled in papers? It's typically used to make a certain point or as stand-alone journalism, whereas you seem to view art as an outlet, a new way of viewing and describing the world.
Illustration has recently begun to have a more important role in newspapers, in part because of advances in color reproduction. But too often art is simply used for info graphics or spot illustration. The Op-Ed page of the Times allows illustrators to make their own statements. I admire R. Crumb's and Bruce McCall's and Roz Chast's pieces in The New Yorker, Ralph Steadman's contributions to Hunter Thompson, and most of all the late Ronald Searle.

I think of myself as a journalist in the literal sense of the word. I create my art in journals, I document what goes on around me constantly. Drop me into an unusual situation and I'll emerge with a document chronicling that event. My approach may be different from the typical print journalist, but I'm still there to catch the story, and my advertising background has helped me to distill things, to get to their essence.

Would newspapers benefit from including more work like yours?
Absolutely. I'm pretty good at ferreting out the absurd, ennobling the mundane, and noticing those small moments of drama playing out in the shadows. My combination of words and drawing can convey the true texture of an event. I can go into a story and cover it like any journalist but my account gets an additional, emotional element through drawings. I get great response from readers who are more visually oriented, who are used to the high-intensity, graphic nature of television. I have a new story appearing in the upcoming issue of Print magazine in which I document several days that I spent at the European sex trade show in Berlin. I interviewed a broad range of people and immersed myself in the story for several days. Readers will be entertained and informed, and get a great sense of what went on there. This summer, I'm planning to cover the Republican Convention.

It seems to me that you're doing exactly the kind of work you want to be doing. You don't appear to be constrained by any limits. Do you ever have to compromise, particularly in the work you do that's not for personal pleasure or your books?
Over the last few months, I've been hired by several publications to do illustrations. At first, that was a bit of a challenge, simply because I was fitting myself into somebody else's conception of what I do. But I think my experience in advertising made that reasonably easy to get over. And while my blog is something I define myself, I am aware of the people who read it and put a certain amount of effort into trying to meet their needs too. Creating something for public consumption has certain rules. The things I write and draw for my blog are somewhat different from the private journal work that I do, although there's a lot of overlap. I've never felt that that's given short shrift to my own expression.

On the other hand, you seem to enjoy collaborating. Is it easy for you to work this way?
Again this may go back to my career in advertising. I've been used to having a partner and I worked with a range of different people in creating ads and commercials. I find it fairly easy to work with other people. That's particularly true when I'm not doing work of a very personal nature. Then, I become more of a territorial bastard.

In a book about author Isak Dinesen, I read a line that made me think of you: "All sorrows can be borne if put into a story." Do you think that's the case with your work?
I think there's a certain amount of truth to that. By telling the story of my wife's accident, I've given it certain parameters, made it perhaps easier to digest. At least I think it's true for other people. What could be an unbearable, horrible story is somehow easier to take once surrounded by cute drawings. But the point of the story for me was to encourage myself and others to search for meaning and beauty in the rest of life. Drawing has given me a way to see my reality more accurately, to live in the now and not obsess about what might happen. Sometimes that's painful, but most of the time it's a blessing.

Chris Gage, a frequent contributor to, is a production editor at John Wiley & Sons. You can buy Change Your Underwear Twice a Week, by Danny Gregory, at

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