Remembering Woodstock ‘99

Jason Myles

August 22, 2022


The Woodstock music festival has, at least in the United States, come to define rebellion and the counterculture for the baby boomer generation; an image immortalized, in no small measure, due to a 1970 concert album. In the summer of 1969, some three hundred thousand or more peace-loving, tie-dye-wearing, love children with flowers in their hair and hope in their hearts gathered at a dairy farm in Bethel New York to listen to acts ranging from Janis Joplin to Jimi Hendrix. For these youths (or at least so the mythology that has grown up around this festival tells us), there was a desire to live in a world that differed from the staid conservativism of their parents. Those who gathered in Bethel rejected consumerism, militarism, and reactionary sexual morality.


This picture continues to be perpetuated in the media, the most recent examples of which are HBO’s Music Box: Woodstock 99: Peace, Love, and Rage and Netflix’s Trainwreck: Woodstock ‘99. Significantly, both documentaries take as their subject Woodstock ‘99, a festival held on the 30th anniversary of the iconic original. Both forward a similar thesis, seeking to counterpose the “peace and love” vibe of the original Woodstock with the “rage” that defined the 1999 revival, an event that ended in chaos and disorder. In doing so, however, they sustain the counterculture mythology, obfuscating some of the realities that surrounded the history of the Woodstock “brand.”


Bad Business


Whatever its cultural impact, the original Woodstock in 1969 was, in many ways, a disaster, undone by a host of technical and logistical issues, and marred by the fact that three people lost their lives. The organizers were unable to recoup their investment as many attendees got in without a ticket. This financial loss, running into the millions, was further compounded by countless post-show lawsuits. However, the way that Woodstock was imprinted on American popular culture provided opportunities. 25 years later, the festival’s creators attempted to cash in on the resurgent 60s nostalgia with Woodstock ‘94.

Woodstock ’94 paid homage to the original, with a line-up that sprinkled in acts that had played in ’69 with the pop punk and rock artists of the day. However, logistical problems again reared their ugly head. Much like in 1969, a hole in the fence created another free show. Around 350,000 people attended a concert for which only 164,000 tickets were sold. The vast number of attendees created a myriad of problems for the enforcement of show policies regarding bringing in food and beverages, coming and going, and sanitation management. There was also a human cost. There were only two reported deaths in 1994, but thousands of concertgoers were treated for medical issues and eight hundred were hospitalized. The result was another multimillion-dollar loss for promoters. But, despite this, the brand remained solidly implanted in the public mind as the embodiment of peace and love.

Despite the financial failures of the previous two Woodstocks, the 30th anniversary in 1999 provided yet another opportunity for the ’69 organizers to make back their losses. This was aided by an Oscar-winning documentary that helped cement the narrative of Woodstock as a defining moment in music and a major success of the counterculture.


Woodstock ‘99: Third Time a Charm?