The biggest letdown about Woodstock 99 involves its attempt at drawing wider conclusions about why the whole debacle still matters: "Monica Lewinsky, Britney Spears, Kurt Cobain, Fight Club, The Matrix, American Pie, Columbine, Girls Gone Wild, Napster, Maxim magazine, and the Y2K scare all earn screen time, but they feel like dropped names (or I Love the ’90s signposts) rather than truly connected dots," says Marc Hogan. "Meanwhile, a powerful figure like one of Woodstock ’99’s spiritual godfathers, Howard Stern, who said of the fest at the time that 'the cool thing was chicks were really into taking off their tops,' goes unscathed.There’s chilling footage of the late rapper DMX leading the crowd in a call and response to his lyrics, and a sea of mostly white people gleefully shout back the N-word."
And there was rampant raunch culture – the kind skewered in two other breakout films of the year, Promising Young Woman and Framing Britney Spears – which figured women’s bodies as first and foremost for the enjoyment of men.With Woodstock 99, the sell of 60s idealism curdled into the license to take, to do things not permitted off-grounds. There was the reaction to the chart-dominating teen pop of Britney Spears, ‘NSync, and the Backstreet Boys with overtly aggro acts like Limp Bizkit (choice song: Break Stuff). "There’s the doomed impulse to reboot a highly romanticized moment for Boomers (the original Woodstock was, in reality, a mess, a few shades of luck from tragedy) into a money-maker for young college kids – part of a cultural pattern of “Boomers pushing their beliefs on younger generations”, said Price. " Woodstock 99 untangles many of the threads that combusted into what looks, by the end, like a burning apocalypse through a heap of archival footage and interviews with participating musicians such as Moby, Korn’s Jonathan Davis, and Jewel, attendees and music critics," says Adrian Horton.