"Milton Glaser's Bob Dylan is a romantic icon in the end of the 1960's. This art work is one the most famous. It has been printed over 6 millions time, and included in the 1966 album "Bob Dylan's Greatest Hits". Inspired by the tradition of american graphic art, the silhouette cutted by Marcel Duchamp (Black on white profile), this illustration is a striking work and projection of Milton Glaser's art, and more widely from the New-York scene, a union bound between the United State and the old European continent." - From "L'affiche, paroles publiques" - Diego Zaccaria.
This specific design mostly attributed to "psychedelic pop-art" , by which Peter Max is a phenomena, has also been used by the productor of "Yellow Submarine" - From The Beatles: Heinz Edelmann. This one has asserted his filiation to Milton Glaser regarding his work.
Milton Glaser is also the maker of “I love New York” logo, worlderly known and happily plagiarized in many ways.