The work of Fillmore poster artist David Singer is a sub-genre of poster art in itself. Singer’s output was the largest of any single Fillmore poster creator. The artists’ photo collage style sometimes gets overlooked initially as it is not as overtly psychedelic as some of his predecessors’ illustrations but it is loaded with symbolism. This Grateful Dead poster was made for an historic run of shows by the band. These four nights at the Fillmore West were the very first after the release of “Workingman’s Dead” and featured a rare acoustic set each night. The Dead shared billing with the New Riders of the Purple Sage, as well as Southern Comfort, a very short-lived Bay Area quintet.
The roots of the New Riders can be traced back to the early 1960s folk/beatnik scene centered on Stanford 's Perry Lane housing complex in Menlo Park, California, where future Grateful Dead guitarist Jerry Garcia often played gigs with like-minded guitarist David Nelson. The young John Dawson (also known as "Marmaduke") also played some concerts with Garcia, Nelson, and their compatriots while visiting relatives on summer vacation. Enamored of the sounds of Bakersfield-style country music, Dawson would turn his older friends on to the work of Merle Haggard and Buck Owens and provided a vital link between Timothy Leary's International Federation for Internal Freedom in Millbrook, New York (having boarded at the Millbrook School) and the Menlo Park bohemian coterie nurtured by Ken Kesey.
In the summer of 1969, John Dawson was looking to showcase his songs while Jerry Garcia was looking to practice his brand new pedal steel guitar. The two played in coffeehouses and small clubs initially, and the music they made became the nucleus for a band—the New Riders of the Purple Sage.
That same year, David Nelson, expert in both country and rock guitar, joined the group on electric lead guitar. Filling out the rhythm section in those early days were Grateful Dead drummer Mickey Hart and engineer Bob Matthews on bass, who was later replaced by Phil Lesh. In 1970, Dave Torbert took over on bass and the New Riders played every chance they got. Soon enough, smoky clubs all over the San Francisco bay area were filling up with whooping, foot-stomping crowds as their music got tighter and more dynamic.