The film features interviews in which the concert promoters, workers, performers, and attendees share their experiences of the infamous 3-day festival that was marred by intense heat, overpricing, violence, sexual assault, looting, vandalism, and fires.
Director Garret Price said in a 2021 interview that he thought the late 1990s had a “toxic” culture. Price reflected that when the festival took place, he and his college roommates “were glued to the pay-per-view that whole weekend”, adding “It’s weird, though, as all that chaos unfolded in real time, it never felt crazy to me back then — it was almost like this extreme FOMO, wishing I was there. It wasn’t until years later when I started going down a YouTube rabbit hole of reliving the performances and reading articles that I started to understand all the issues that started to unfold that weekend. Not just of the festival itself, but of America culturally.” Price also remarked, “I think the reason the ’90s are so in right now is that people are nostalgic for the decade they were born in. So kids at Woodstock ’99 were nostalgic for the mid-late ’70s, with Dazed and Confused being popular. But Woodstock ’99 tried to push a nostalgia for the last ’60s, and the ideals of counterculture and free love.”