In Memoriam: Milton Glaser, Graphic Design Master who inadvertently brought Dylan and the 60s music scene to Woodstock

Milton Glaser, the master artist who created many of the most popular images of our times, from logos for IBM, DC Comics, UPS, Brooklyn Brewery, and ABC, to the iconic “I ♥ NY,” has passed away at 91. For we devotees of music, and especially New York State music, Glaser also holds an interesting place, as the man who inadvertently helped bring Bob Dylan and many figures of Sixties music and beyond to Woodstock.

According to Barney Hoskyns must-read history of Woodstock and its music scene, Small Town Talk, it was Glaser who we may largely have to thank for Dylan’s relocation to Woodstock.

As told in Hoskyns’ book, Manhattanite Glaser and his wife Shirley owned a second home in Woodstock since the 1950s, where they often entertained city friends, including Dylan’s famed manager Albert Grossman. It was natural for Milton Glaser to be drawn to the town since it has a history in art going back to the founding of the still-going strong Byrdcliffe, America’s first art colony in 1903.

When a large property with 60 acres of land became available in 1962 in adjacent Bearsville, for the then princely sum of $50,000, Glaser immediately thought of Grossman. As quoted by Hoskyns’, “We didn’t know a single person with $50,000 except Albert,” said Glaser. The fact that Grossman resembled a bear may have also played a role in his choice of location, according to Glaser.

Though Dylan first came to Woodstock in 1961 to stay at a cabin owned by the family of Peter Yarrow of Peter Paul and Mary, another Grossman-managed act, it was the comfort and protection of Grossman and his wife Sally that finally made him settle, as a way to escape the crazed demands of his stardom. Dylan lived in several homes in the area and was followed up by his backing band, The Band, who took up residency and created a musical workshop at the famed but decidedly humble Big Pink in West Saugerties, from whence the famed Basement Tapes emerged.

milton glaser
Lightnin Hopkins album cover by Milton Glaser

In time, many more would follow to become full and short-time residents including Van Morrison, Jimi Hendrix, Paul Butterfield and Janis Joplin, another Grossman-managed artist, and more recent names like David Bowie, B-52 Kate Pierson, King Crimson bassist Tony Levin, jazzers Jack DeJohnette and Pat Metheny, to name a few. Goldman went on to expand the musician attraction offerings in Woodstock by creating Bearsville Recording Studios and the soon-to-reopen Bearsville Theater.

Glaser was also famed for his poster art, creating more than 400 at his Push Pin Studios. One of his most famous was one he created for the 1967 album, Bob Dylan’s Greatest Hits. Here, he drafted a simple outline of the singer’s head, based on a black-and-white self-portrait silhouette by Marcel Duchamp, and added thick, wavy bands of color for the hair, forms he imported from Islamic art. Nearly 6 million copies made their way into homes in America, making it one of the most popular wall hangings on the bedrooms of young people in the Sixties. Glaser also produced a slew of album covers for artists including Paul Simon, Peter, Paul and Mary, Doc Watson and Townes Van Zant.

milton glaser

For more on Woodstock music history, pick up Barney Hoskyns’ Small Town Talk, which features a handy map to many of the former homes of the music stars. For more on Glaser and his art career, read today’s obit in the New York Times.

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