Arguably the most famous image of Bob Dylan is not a photograph or painting, but a drawing: a suggestion of the man rather than a precise, dead-ringer likeness. And that's fitting. After all, what better way to celebrate Dylan's kaleidoscopic sensibility than with a fanciful, yet recognizable, portrait?

50 years after record-buyers discovered just such a portrait in the form of a poster tucked inside Dylan's first Greatest Hits album, that image—created by the legendary Milton Glaser—has lost none of its power, or its appeal.

Dylan's Greatest Hits was released March 27, 1967—rushed out the door by his record label, Columbia, between the release of two other albums, the earth-shaking Blonde on Blonde and the lovely, underrated John Wesley Harding. Between March 1965 and December 1967, Dylan released no fewer than four classic albums—including Bringing It All Back Home and Highway 61 Revisited—in addition to the five-time platinum Greatest Hits. In those heady years of the mid-Sixties, any number of bands sold more records than Dylan, but no other musical act on the planet—not the Beatles, not the Stones, not Hendrix, no one—was more influential.

For his part, Glaser acknowledges that his Dylan poster—with its stark black silhouette, explosion of color and its employment of the Baby Teeth font that Glaser himself designed—has earned its prestige. It has endured in the popular imagination, and in the marketplace, for a half-century—an eternity for something as ephemeral and of-its-time as a rock & roll poster.

"This is the mystery of art," Glaser said during a recent conversation at his large, clean, well-lighted studio in Kips Bay. "Some works have a profound effect on us. They last, while others fade away. Why?"

A sketch of the Dylan poster. (Scott Heins/Gothamist)

Glaser is the dean of American graphic design and creator of many of the most indelible logos and emblems any of us will ever see—including, first and foremost, "I ❤️️ NY," which might be the single most frequently reproduced design in history. He is 87 years old and quite tall, although these days he walks with a slight stoop. He has a ready, knowing smile. His warm, keen, hooded eyes are the most striking feature in a thoroughly striking face.

He wears patterned silk neck scarves indoors and succeeds in making what might seem an affectation in a less-confident man appear, instead, effortlessly natural. He is old-school, but far from old-fashioned. He's very cool.

Glaser still goes to work every day at the studio in the East 30s that has been his creative home for the past five decades. (The studio lives in the same four-story building, by the way, where Glaser and Clay Felker started New York magazine in 1968.) On a window above the building's street-level double doors are three words that sum up Milton Glaser's lifelong vocation: Art is Work.

The design for the Dylan poster was inspired, Glaser says, not by Dylan's signature look—the unruly head of hair, the distinctive profile—but by a Marcel Duchamp self-portrait that Glaser first encountered as a teen.

Glaser's Dylan poster

"When I was in high school," he says, "I saw a self-portrait by Duchamp, a simple cutout silhouette that just floored me. The power of it was staggering. It had no detail at all, just Duchamp's profile cut from a piece of paper. I wanted to know how something so elemental, so simple, could move me like that. In a way, that question has extended to my life's work. Why do people prefer one thing, or react so strongly to one thing, while another picture or piece of writing or music is quickly forgotten?"

Of the Dylan poster, he asks, "What is it about that image that has made it a desirable object for so long? Yes, it's linked to that moment in time, a nostalgia for that era. But that's not the whole story. Last year, I spoke at the Guggenheim about the distinction between design and art, and the importance of understanding that distinction. Design is always purposeful. You're addressing an audience, because you want to motivate them to act—to buy something, usually. Art, on the other hand, is a mechanism for transforming the brain so that human beings can find commonalities. Art is a survival mechanism. It was invented to help us learn how to share an experience, meaning we're less likely to kill each other.

Every once in a while, though, a work of design enters into that realm where it becomes a link between people—a shared experience rather than a mere call to action. When I ask Glaser if his "I ❤️️ NY" design falls into that category, without missing a beat he makes a rather remarkable leap far back in time in order to illustrate his point.

"Ever since the Big Bang," he says, "we've all been made of the same material. Everything and everyone is connected, but every once in a while the mind is stimulated toward a recognition of an even deeper connection. 'I ❤️️ NY' was introduced in 1977, and to this day I can't walk down the street without seeing it four, five, six times. Partly I think it endures because it was never just a marketing device, even if it was part of a campaign to promote tourism. It was an expression of how people felt about New York during a very, very tough time in the late '70s. We wanted to let the world know that we still loved this city. It was emotional, and it was real."

Glaser shrugs.

Glaser's 1976 sketch of the logo, and the finished product.

"Why does the Dylan poster persist? What do people get out of it that makes them feel enlightened, or transformed? I don't know. This is a mystery that can't be resolved, because it's not rational. It's not objective."

The Dylan poster is a collectible now, with buyers paying hundreds and even thousands of dollars for an original that started life as a freebie, folded into an album cover 50 years ago this month. Glaser's studio still gets hundreds of orders a year for reproductions of the poster ($100, or $200 signed)—extraordinary testimony to the power of that unresolved mystery.

I ask Glaser one last question: Countless people claim to see the word "Elvis" in the swirling rainbow of Dylan's hair. What's the significance of that?

Glaser shakes his head.

Glaser in his studio. (Scott Heins/Gothamist)

"Well," he says, "I have to say that was not intentional. In fact, it didn't even occur to me until 15 years later when some critic said that he saw Elvis's name there. He thought it meant something. But it doesn't." He shrugs again. "Or maybe it does. All this stuff goes on beneath the surface, in the unconscious. You never know what the fuck you're doing and why you're doing it."

I suggest that maybe that is overstating the random, mysterious nature of art.

Glaser nods.

"I've had the compulsion to draw ever since I was five years old. I went to art school to learn life drawing when I was 12. My whole life has been devoted to this thing called art, which is really all about making things. It's about the physical act of transforming material into something else. For many people, that is the great learning tool and the great joy of life -- this idea that you sit down and out of nothing, you create something."

"Art is work?" I ask.

"Art is work," Milton Glaser says. And he smiles.