Bob Dylan Original Vintage Poster by Milton Glaser, 1967

Milton Glaser may be best known for a 1977 doodle that became his hometown’s unofficial slogan: I ♥️ NY. But the Bronx-born graphic designer had many other successes during his nearly 70-year career, including iconic posters and prints and cofounding the groundbreaking design firm Push Pin Studios.

In the 1950s, American graphics tended toward a Swiss-influenced precision. Glaser, however, pulled from the whole of art history for his designs, inspired by his studies with the painter Giorgio Morandi while on a Fulbright scholarship in 1952. His famous Bob Dylan poster, a landmark of the psychedelic age, was inspired by a Marcel Duchamp self-portrait and the jewel-like colors of Islamic art.

A cofounder of New York magazine, Glaser went on to design for scores of other publications, and in 2009 he was awarded the National Medal of Arts.

In an instance of life imitating art, Glaser was asked to create the promotional posters for the final season of Mad Men, which aired in 2014 and 2015. “I could have walked in the door of that firm,” the designer told the New York Times of the fictional Sterling Cooper & Partners. “I knew those people.”

“There are three responses to a piece of design — yes, no and wow!” he said. “Wow is the one to aim for.” Glaser rarely, if ever, missed the mark. He died of a stroke in 2020.

Find a collection of authentic Milton Glaser art on 1stDibs.