Carson McKenna
6 min readOct 10, 2021

Re-examining Woodstock ‘99

In spirit of the 90s revival, let’s revisit the. festival with an identity crisis who haunts the annals of ‘99

We all know the 90s are back. Seemingly overnight, my Instagram became a runway of chokers, baby tees, and inflatable furniture. To look at how the Gen Z girls at my work are dressing, I would have thought I woke up in Seattle, and Kurt and Court are both alive and well.

Britney, our Pop Princess ‘99, has basically been canonized in 2021. Dawson’s Creek and Seinfeld are in the Top 10 on Netflix, and so is Titanic. I find myself philosophizing on the “Dawson versus Pacey conundrum” with my fellow millenial fillies, as if tomorrow’s another Thursday night in Capeside.

I can barely name the pop titans and taste-makers of our time, maybe because their monikers don’t seem to carry the same weight of their forbearers. Sure, the Hadid sisters are beautiful, but are they embossed on our collective soul in the way that doe-eyed Britney in her tartan skirt is? Same goes for Hailey Bieber, her cousin Ireland, and the whole Kardashian clan: if they magically disappeared tomorrow, would we seek them out later in a yearn of nostalgia for what they represented in our feminine identity? I’m not entirely convinced I would…

A part of me never left 1999. I’ve said for years that ‘99 was the golden year for pop culture. All the most iconic teen movies came out that year (I will give them their due delineation in a subsequent article). So did Fight Club and the Matrix (two films as universally endorsed by straight men as Joe Rogan). I’m sure entire dissertations have been written about the significance of 1999 in cinema, but for now I’ll just focus on the music of the dawning Millenium (or Willenium, i mean)

Woodstock ‘99

Personally, I was 11. I can remember hearing about Woodstock like I can remember hearing ‘Genie in a Bottle’ blaring every day from the counselor’s cabin at Camp Sertoma.

Yes, I wished I could attend. Didn’t you? Everyone knew about Woodstock ‘69. All the people responsible for the songs that we would be cursed and blessed to hear forevermore were there (and like three of them died the following year). The thought of recreating it, while also infusing my lords, ladies, and lieges of J-14 and VH1 was too much Nirvana to bear (oops — how morbid. I’ll say too Sublime instead).

But the festival was trying to breed a scaly reptile with a Funfetti cupcake. First of all, they had Carson Daly out there, the friendly fraternal face we welcomed into our living rooms every day after school. Carson was the key holder for all things au courant, telling us who was #1 on TRL each day. Usually that person was someone Slim Shady riffed on in his songs.

Carson tried to report on the festival for MTV, but the attendees booed him offstage, even pelting him with garbage. There were Backstreet Boys cut-outs on said stage, and the crowd sieged the dais and kicked the aviator goggles right off of AJ McLean. Gulp.

So who did they want instead? Well, the lineup also included the likes of Korn, Kid Rock, and Limp Bizkit. Like Eminem, these guys were emerging as a middle finger to the pop wave providing the soundtrack to school dances across America. Unlike Eminem, (who I believe to be the Bob Dylan of my generation) they weren’t lyrical geniuses. Their message basically was, “Fuck you if you don’t like me.” I think Kid Rock actually said that as he sashayed onstage. He also said, “Bill Clinton is a fuckin’ pimp and Monica Lewinsky is a fuckin’ hoe!” The crowd cheered rabidly. Girls who were moshing reported having their clothes ripped off, and fingers shoved inside them. I know correlation doesn’t always equal causation but liiiiike.

The crowd was restless and jumpy all throughout the performances by Alanis Morsette and Jewel. It made perfect sense that these two minstrels were invited: they were both undisputed ambassadors of their generation. But this wasn’t the 90s vibe their stars had risen under. The vibe of Jewel and Alanis was soulful and vulnerable — representing conversations in coffee shops fueled by espresso paid for in quarters; flannels and beatnik shades; jeans with t-shirts tucked into them; roommates scribbling your messages on a pad beside the phone; the tender angst of Ethan Hawke and Duncan Sheik, and the joyful liberty of leaving your house and being utterly unreachable.

I think this vibe — of newness, first love, first heartbreak, experimentation, and learning ones likes and dislikes (in boys, girls, food, music — everything) — is the nostalgia we are all trying to return to.

I think the vibe we are trying to escape is the angry, testosterone-fueled dystrophy that plagued Woodstock ‘99. That, “if you don’t like it, suck my dick” reptilian chauvinism that we’ve all experienced as many times as the common cold (men experience it as well, and it conditions them accordingly).

Woodstock ‘99 ended in a hellish blaze. Some attendees started a candlelight vigil for the victims of Columbine (which had only happened three months earlier). Somehow, those candles were used to torch the campsite. The concert turned into a mob that ripped up the stage and the surrounding walls. Police were called, but few arrests were made (side note: there were next to zero people of color at this event…but that’s probably just a coincidence, right?). A man died from dehydration (bottled water was sold at $4 a bottle, and outside provisions weren’t permitted). Countless women reported being raped.

There is a lot of commentary that could be made about Woodstock ‘99: it could be said that it was predatory for placing an unethical bounty on water and food (call me Karl Marx, but that ain’t capitalism). You could say it was an civil war of pop culture, in which the Fred Dursts had it out with the platinum princes of TRL. You could say that we were all hurtling towards the uncertainty of a new millennium (Y2K?) and in recovery from two years of the president’s fellatio scandal (“I did not…have…sexual relations with that woman…”). After all, when the president’s mistress is discussed so breezily and liberally, why be surprised when men treat all women like Monica? She becomes theirs to comment on and to postulate sexuality on, reduced to a gross punchline in a card at Spencer’s.

Maybe it’s a Frankenstein quilt of all of the above, but it’s still worth reflection.

In signing off, I’ll bring Jewel back into the chat. She said that Woodstock ‘99 was her generation’s thwarted attempt to come together, because they had no real “cause.” Unlike the Greatest Generation, who were united by war, and the Boomers, who marched against it, Generation X had no one event or core ethos to truly unite them. The history that characterized their time (Kosovo? Desert Storm?) holds up as more of an, “oh yeah, that…” than a defining, cultural moment in the vein of 9/11 or #MeToo. Even their technology (the walk-man, the pager) have become fossils of antiquity swallowed up by the tech barons of Cupertino.

But I’ll also say that the legacy of Generation X is one of nostalgia: your millennial and Gen Z little brothers and sisters yearn to be you, sitting in a cafe in 1996, in blissful ignorance to the world beyond your coffee cup, because it doesn’t exist in the palm of your hand, on a five inch screen with a chrome Apple on the back.

ACKNOWLEDGEMENT: I would like to applaud Dexter Holland, the lead singer in Offspring, who performed at Woodstock ‘99. When he saw women being groped while moshing, he called the guys out in a funny and femme-positive way. Look up the clip.

Also: I watched the Woodstock ‘99 documentary, ‘Peace, Love, and Rage’ which partly inspired this article. I heartily recommend 👍

Carson McKenna

Top Writer in Love 😍 curious human, pro-bono anthropologist - Author of, "Broke Babe in a Basement" available on Amazon now! 🦀 ♈️