Before Steven Heller authored over 170 books on design and visual culture, before his column for the New York Times and his unbeatable Daily Heller newsletter, and even before his time as an art director for the NYT Book Review, the acclaimed critic was navigating the ins-and-outs of the political underground press in Manhattan.

It was there that Heller first found his route into writing and art direction. Today, he tells us the story of his time illustrating for The Free Press and how that led to the launch of his New York Review of Sex.

“I always wanted to be a cartoonist in the mould of Jules Feiffer (mostly), although I loved MAD magazine and Virgil Partch (VIP). But, sadly, I lacked the necessary chops.”

“I could make marks and devise ideas, but I was not as good as my heroes, which later included Ron Cobb and Robert Crumb. When still in high school I took a portfolio around to all the New York hippie, left-wing, and underground papers (I had been rejected by The New Yorker) to see if they would be interested in publishing something.

“I hit pay dirt with The Avatar, The Rat, and The Liberation News Service, which sent my stuff to papers around the U.S., but to my great surprise, two months before graduating from Walden School in NYC and six months before going to NYU to study English, I was hired to do paste-up and draw pictures for The New York Free Press.

“The art director was the later famous J. C. Suares, and when he left a week after I started to begin another magazine, I was hired for $50 a week to be the art director and resident artist. Periodically, the editor would ask me to do the cover, so I drew as best I could. I was terrible with life drawing, I knew nothing about Expressionism or Surrealism, but I kind of did it instinctually. Also, my lettering skills sucked. So this was what I did:

New York Free Press, Steven Heller’s cover illustration debut

“I worked with a crow-quill pen and India ink, and loved making little details, like those in the wings. The character in the talons was my alter ego—helpless, naked, and horrified.”

“I was of age for the Draft (Selective Service) and Vietnam was exploding. So the “brief” expressed what I and lots of other red-blooded, rebellious, privileged middle class liberal kids felt—NO WAY JOSE! I was not going into the military. I had gone briefly to a military school, but that was before the idea of going into a battle zone scared the crap out of me. I became an anti-war advocate, first in a self-serving way, and then learned a lot about how our government was abusing its power in that part of the world. My ignorance slowly evolved into political conviction and a left-leaning sense of justice that put me at odds with the older generation.

“Looking at my first cover illustration now, I think I’d probably do the same thing, though with better type. I learned how to design somewhat at The Free Press, but not how to draw any better. I still doodle the same way.

The New York Review of Sex came out of my time with The Free Press, which was the home of Screw Magazine. I had illustrated a story by Al Goldstein, co-founder of Screw (with Free Press managing editor, Jim Buckley), and was asked to be their art director. The result of my design ignorance was apparent. The issues that I did were awful. But I did a comic strip, which featured my NYU philosophy professor. Believe it or not, that strip got me thrown out of NYU. I left Screw because of an argument over a logo. And The Free Press cut its ties with Screw for other reasons.

“But as revenge, we decided to start The New York Review of Sex (and politics). It’s a long story… so suffice to say, when we began the NYRS, I wanted to make it look better than Screw. So I convinced my co-publisher (I was publisher and art director and, under the name Michele Lee, I was advertising manager, too) to invest in full-color and 50 lb newsprint (heavier paper than Screw). I ended up doing a Feiffer-like comic for NYRS and commissioned others to do illustrations, including Brad Holland and Rick Meyerorwitz.

“We got many of our photos from the Japanese artist Yayoi Kusama, who is now very famous.

“I had a free hand to do whatever I wanted visually. I thought I was being a ‘good’ designer, using real typositor type and sometimes Morgan Press vintage type. It was still not up to snuff with design you’d see at AIGA or the Art Director’s Club, but I thought it was better than other underground papers. 

“I realized that this was the kind of work that I really wanted to do, and I wanted to become great at it. I saw what great illustration looked like, so I stopped doing my own (until I went to the New York Times’ pp-ed page, and when I ran out of budget, I assigned myself illustrations—mostly collages—to fill the deficit).

“The NYRS issues were not great, but I felt my ability to be a feature editorial designer and typographer was better than when I started without any knowledge. The NYRS folded after we were arrested a few times, and then I became the art director of a music magazine called ROCK. I liked a lot of what I did for it. Then I left, went back to Screw, and from there to the New York Times for 33 years.

“During my time doing NYRS, I learned that I loved this. I learned that I needed to learn more, but I was not going to learn it in school, which may have been a huge mistake on many levels.

“Over time I learned that I was a better art director than a designer. I learned that I actually preferred writing about design than doing it. I would not change the course of those experiences for anything in the world. I learned that design, art direction, or whatever the visual media process is called, was more about what you said, than how you said it. Then I learned that saying it well—with flair, ingenuity, and even beauty—would help the message reach more people.”