A prolific graphic designer, illustrator and raconteur, the 78-year-old has created hundreds of book jackets, more than 300 posters and 50 magazines. He cofounded the seminal illustration and design agency Pushpin Studios in 1954 and New York magazine in 1968, and is the subject of the illuminating documentary To Inform and Delight: The Work of Milton Glaser, recently released by Checkerboard Films. Alice Twemlow visited him at his Manhattan studio to discuss design, Dante and psychedelia.

Why do you think the I❤NY logo you designed in 1977 is still so popular?

I think the reason that certain images remain in the culture is that they contain some degree of difficulty, but you have to allow people to resolve that difficulty very quickly. In this case, it’s a simple puzzle: “I” is a word, ❤ is a symbol for a feeling, and “N” and “Y” are initials for a place, so you have to shift three times between the different meanings of these forms.

Tell me about the strategy behind your recent “We are all African” poster, which protests the lack of response to the situation in Darfur.

The tool that is most powerful in terms of changing people’s opinion—after fear and punishment—is empathy. If you can convince somebody that “they’re like me,” then you can convince someone to buy in to something. The fact that we all physically came from Africa is the basis for the poster’s image, which shows a black hand with the five fingers in the skin shades of the different races. Not only is it a slogan— it’s true. It’s always good when a slogan is true.

Picking the right slogans is clearly important to you. Do you start with the words first or the image?

I never separate words from images. I’m very concerned with narrative. One of the reasons I focus on words and storytelling is because I began my career with a passion for illustration.

Tell me about your “12 steps to hell” for designers.

According to Dante, people in hell don’t know what they’ve done, while people in purgatory do and therefore have the ability to get out. With my “road to hell” test, I want designers to acknowledge their own position. It amazes me that when I give this to my students and we get down to the last question—Would you design an ad for a product whose frequent use could result in the user’s death?—about 5 or 6 people in a class of 20 say yes. Unfortunately, many young designers have the incorrect assumption that this is what professionalism is about.

Something else I think you’ve taught young designers is the importance of distribution.

The physical thing you make is only one part of design. You have to think about where it goes, who pays for it, how it is made. The difficulty is that people have to deal with a relentless attack of information every day. Most people defend themselves against that everyday crap by deflecting stuff. The question for designers is how you penetrate people’s resistance to everything around them.

There’s a renewed interest today in the seepage between art and design. Can you reflect on your own struggle with this issue?

This issue is baloney. You have to examine the self-interest involved in establishing such a distinction. How did Keith Haring enter the halls of art? He’s a cartoonist. What was the process by which he became a viable and marketable artist? How did they get $200,000 for a cartoon of his that used to be drawn on the subway? Well, you get anointed. Someone says there’s money to be made, and then the wheels start turning.

Do you collect art?

I used to. My wife, Shirley, and I had 130 pieces of African sculpture and a nice collection of Persian and Islamic works. But we had to sell or donate them when we moved to a smaller apartment. I thought I’d be sad, but I realized I’d spent so much time looking at them they are all in my brain.

We can’t do this piece without bringing up your poster of Bob Dylan with his curly hair replaced by waves of color. For many it’s the quintessential visual document of late 1960s consciousness, but are there other, more historical references in there?