Dave Van Ronk was a central figure in Greenwich Village's folk music scene from the 1950s onwards, serving as mentor to artists including Bob Dylan and Phil Ochs. A committed progressive activist, he regularly performed at benefit concerts and worked with radical organisations despite the declining cultural landscape of the Village he once championed. On June 28, 1969, while celebrating his 33rd birthday at the Lion's Head bar in Sheridan Square, Van Ronk and friends noticed police activity and commotion erupting outside.

Van Ronk's involvement at Stonewall reflected his longstanding dedication to progressive causes and opposition to establishment discrimination, following decades of witnessing and resisting what he termed the 'culture wars' of the McCarthy era and beyond. Though known for his curmudgeonly demeanor regarding the changing Village, he remained philosophically committed to the neighbourhood's ideals of freedom and acceptance, demonstrated through his presence during this pivotal moment in civil rights history.