Milton Glaser has designed nearly 500 posters over the course of his half-century career. Known by most for his iconic I Heart NY campaign, Glaser is a prolific designer who has wandered down many a stylistic path ranging from illustrated psychedelia to typographic treatments. In his new book, Milton Glaser Posters, the designer guides readers through the long journey of his career, offering insights around each poster—what worked, what didn’t, and how every individual piece is an opportunity to learn something new. “I hope everything I do is a path to some kind of understanding,” he says. Here are five posters from Glaser’s career and what they meant to him.

I view all my work as a single continuous path. There’s nothing that I do that hasn’t had some effect on me. In this case, the drawing of the stylization of the hand seems extremely clumsy to me in terms of the way I conceptualize a hand now. At the time it was what I was doing, and I did the best I could. Also I don’t think that was a particularly good poster as it were. It’s not a bad drawing, but sometimes a good drawing can be a mediocre poster, which is to say it doesn’t inform you perhaps enough about the spirit of the film or give you an adequate reason to go see it. If I were to class this poster in terms of its position in the total work that I’ve done, I’d put it in the lower 10 percent. But your judgement about these things changes as you go through your life; you modify your belief system.

Information gets interesting when it’s first announced to you. A fact about a subject is interesting if you didn’t know that fact and someone makes it available to you. After a second iteration, you might continue this interest except knowing you’ve heard it before, and now that interest becomes more solidified. By the time you reach your third iteration of the idea, you’re at the point of boredom where you say, “I’ve already heard this several times, and it’s no longer amusing or surprising to me. Consequently I’m not sure I have to pay attention to it.”

We depend on cliches and repetition to establish context for learning. If you’ve never heard something before, you have to make a vigorous attempt to understand something, which requires attentiveness. And the secret of communication is how you generate attentiveness in others. You can do it certainly the first time somebody hears something. If it’s only partially understandable you can take it to the next step of being fully understandable. But if there’s no understanding of something, it’s incomprehensible. That’s why you need cliches. You need things that form the basis of your future understanding. You have to know how to use a cliche and modify it so it retains its interest.

In this case, it’s an example of repetition producing a difference. You take a single image, a rising sun, and then you repeat it and it’s a different kind of rising sun. You repeat it again, and suddenly you have a panorama and the panorama is made out of elements you’ve seen before but never combined in this way. After all, in terms of what graphic designers do, combining existing things is most of your work. Most of your work is not work that you’ve originated but that you’ve assembled.

This was an announcement for a show my wife curated when she was gallery director. It was a show of transparent sculpture. At the time, sculptors who were working with acrylic and other transparent materials to produce different kinds of sculptural entities. I thought I would do something to symbolize two things a) sculpture and b) transparency. A rather obvious choice.

Someone looking at this wouldn’t see it as an abstraction; they’d see it and say, “Oh I get it; it’s transparent and it’s three dimensional.” There the actual content of the subject matter itself led inevitably to the solution. I would say for my work, the first thing I look at is what is it that you want to convey to your audience? What are the most important things about this subject that you want to say, and how is it distinguished from all other material?

One of the issues with communication is that so many things are communicated without attention to what their meaning is. They’re basically a decorative object that looks good. The theory being, if something looks interesting you will read it. And if you read it you’ll understand it. That’s not quite the way I go about it. I go about it where the form itself comes out of the nature of what you want it express. It’s not imposed on an idea afterwards; it emerges from the idea.

This raised a lot of questions in my mind because it’s a poster for somebody whose vocabulary is not yours. The question is: what can you do that does not misrepresent the subject matter? I did an all typographical poster that has nothing to do with his paintings. It only has to do with a certain kind of coloration and a certain kind of form. The forms have some relationship but they’re not his forms. They’re basically geometric forms. What I was trying to do, and it’s really a tricky thing, is to represent him without using his vocabulary, but using a relationship to his vocabulary. In this case certain colors that wouldn’t feel inappropriate. I always had difficulty with those particular posters because they raise the issue we’re all faced with when we have to do a poster for an exhibition or another artist, which is what do you do except repeat what they have done? That means taking an existing painting and putting some typography on it, and making it feel harmonious and appropriate. It’s a very tricky area of graphic design where you’re using your vocabulary to represent someone else’s work.

There has been a reductive quality in my work. It’s gone from almost the official history of design form the complexity of early design to the simplification and elimination of the extraneous. So if you look at some of my later things, there are very few elements in them. For this poster, it’s a ravioli in the middle of the page.

There’s nothing in that poster except two colors—yellow and red—and a single object in the middle of the page and some serrations at the edge of the pasta and the poster itself. There’s not much in the poster, but it much more represents my view now about reduction and effectiveness without coming out of any ideology about what is reductive. In this case, it comes out of the subject matter.

The pasta, incidentally, isn’t a pasta. It’s a pillow. And so if you look under the pillow there’s a dimension indication that shows it to be a foot long. The idea being, it’s something that looks ordinary until you examine it and then you suddenly discover it’s not pasta, it’s a pillow. That kind of discovery is of great interest to me and has not much to do with a formalistic idea, but really of a narrative idea. I’m very interested in storytelling at the end of a visual experience.