"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. "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. 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). And there was rampant raunch culture – the kind skewered in two other breakout films of the year, <i>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’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."
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. The more recent rap-rock resurgence, from Lil Wayne’s Rebirth to Lil Peep and beyond, is also unexplored. A general line is drawn to American culture today, where wealthy Coachella attendees flaunt VIP badges, and male sexual frustration ostensibly lives on via Reddit forums, but that doesn’t seem to go far enough either—Woodstock ’99 is important, because of Instagram influencers and incels? The film argues that the ’90s were a time of elite control—damn the Man—and 21st-century technology has upended the previous order, so an assemblage like Woodstock ’99 won’t happen again. We all hope that’s true, but considering recent calamities like the insurrection at the Capitol on January 6, it stands to reason that things have actually gotten much worse. Back then, Kid Rock was a jackass rapping in front of an inflatable bottle of Jim Beam; now he’s been to the White House, and your family members on Facebook are convinced that vaccines will magnetize their arms. Pandering to people’s basest impulses is a great way to make a quick buck, but it can also lead to self-destructive chaos."
Woodstock 99 offers a corrective on the original Woodstock: "Multiple speakers in Woodstock ’99: Peace, Love, and Rage provide a corrective to the mythology of the ’69 festival, reminding viewers that, alongside the peace and love of that seminal counterculture classic, there was rampant filth, military intervention to provide desperately needed supplies, and death," says Nick Schager. "In that context, Woodstock ’99 comes across as an extreme version of an inevitability, fueled by music acts that skewed heavily toward the hard rock side and mounting frustration with high prices for the water needed to stave off the dehydration and hypothermia plaguing the 400,000+ in attendance. Catering directly to an entitled frat boy-ish audience—only three women were on the bill: Jewel, Sheryl Crow, and Alanis Morissette, one for each day—and then giving those individuals free rein to act out their at-wits-end worst impulses, Woodstock ’99 sowed the seeds of its own demise, and Price’s doc details the many ways mismanagement led to tragedies."
Director Garret Price wanted Woodstock 99 to feel "like a teen-slasher film": "I wanted it to feel like a ‘90s teen movie — a road-trip movie, where we leaned into the music of the time," he says. "I want this to be like a teen-slasher film, where you have a bunch of kids going upstate for a weekend of debauchery, drinking, sex, rock and roll. I took that idea and ran with it. It was important to go back to 1969, set it up, and use that as a framing device and the mythology around Woodstock and the Woodstock name. I think Woodstock is so huge because of the documentary itself. I feel like a lot more people feel like they were at Woodstock because they saw the film and felt that they were there, but I also had a lot of cultural context that I wanted to introduce throughout the film."
Bill Simmons talks applying the 30 for 30 documentary format to his new Music Box series that includes Woodstock 99: "I had a couple of music films that were the models of what we wanted to do but the main thing was (most) music docs were these beginning, middle and end stories, I call them cradle to the grave, where it’s about the artist’s entire career. What worked for us for 30 for 30 was honing in on specific moments and windows," he says. "The model for 30 for 30 was The Fab Five doc, about a college basketball team that was only together for three years and it’s about that three years. That was probably the one they replayed the most. The question for me was how can this work for music and we tried to figure that out."