Jake Cole’s review published on Letterboxd:
Like a lot of pop cultural forensic dissections, this makes as many frustrating and far-fetched conclusions as it does salient observations. The white male angst on free display in the footage is grist for a number of poignant breakdowns of how the collapse of grunge and the brief wave of progressive male rock stars and women rockers had given way to a backlash against the burgeoning teen pop boom of the late-'90s. Jewel, of all people, perhaps sums up the whole thing best when she describes Woodstock '99 as the culmination of Generation X's rebellion against nothing, of feeling dissatisfaction but lacking the visible, unifying element of a Vietnam or whatever to rally against.
It's that commentary that lands far more than the laborious attempts to create a throughline of white rage leading to Trump. Every time the film really digs into the heart of the matter, that the event was a profoundly cynical collaboration between nostalgic corporate Boomers and MTV frantically trying to maintain its mass-media position amid a crumbling monoculture at the expense of a crowd being bilked to within an inch of its heat-stroked life, a talking head pivots the focus away back onto a current culture war lens. Given that the promoters still sound unrepentant and self-justifying about everything from the price-gouging to the rapes, it's additionally frustrating how the topic shifts every time it seems like they might really be taken to task.
Still, the footage of the event remains stomach-churning, and while editing is everything, you can still feel the bad vibes emanating almost from the start and only getting worse. The film shrewdly points out that Michael Wadleigh's documentary of the original Woodstock defined that event more than anything about actually being at the festival, which was similarly inundated with logistical and behavior nightmares, and if that movie offered a cleaned-up snapshot of a hippie movement that was already in freefall, Woodstock '99 could equally be called a queasy glimpse at how the hollow consensus and ostensible prosperity of the '90s were dumping America into a hellholle state that 9/11 merely catalyzed rather than created.