Photo: Image by stuart hampton from Pixabay

Woodstock at 50: From Glorified Historic Disaster to Modern Day Joke

In part one of our series on Woodstock at 50, we document the troubled history of Woodstock Enterprises and its failure to capitalize on its historic brand. The failure of Woodstock 50 is hardcoded in the organization's past.

It’s 2069 and the most important U.S. milestone isn’t that New York, Chicago, Boston, Miami, New Orleans, and San Diego have disappeared from rising sea levels, or that cellphones and tablets are laughable relics thanks to chip implants in our brains, or that the ride-sharing economy was destroyed by autonomous vehicles or that Black Mirror accurately predicted everything. All that piddling crap is dwarfed by the 100th anniversary of the Woodstock festival, featuring virtual reality versions of all the original performers, who are all long dead by then but are now ‘alive’ thanks to our Live Nation overlords. A brain-chip conglomerate sponsors it, offering ‘Peace & Love’ show packages for a comely $100,000 tab (payable in bitcoin), including a good old 1960s orgy with every single one of the acts, even Quill and Sweetwater.

Ah, but all of this will not come to pass for the Ballad of Woodstock 50 is a long and sad tale which managed to unfold over the last few months and made any future legacy of ‘Woodstock’ almost impossible. To understand what went wrong with the colossal dumpster-fire of Woodstock 50, we have to get back to the garden. In 1969, when the festival first began, the seeds of its own eventual destruction were already sown. Mulling over what happened then shows us what went wrong from the start and carried over to now.


At the start of 1969, the original idea that a foursome had for Woodstock actually centered around what was to be a new recording studio and having a concert to promote it. The studio got nixed, but the concert idea was pursued. It was buoyed on by a Brooklynite named Michael Lang who was hot off the heels of putting on 1968’s first Miami Pop Festival, which was plagued by fights, broken-down fences and later, lawsuits. Even with a historic line-up put together for Woodstock, problems mounted right away for the fest, including where it was going to take place.

Several locations came up and got shot down by July 1969 thanks to poor planning (which would become a Woodstock tradition) and various locales saying ‘not in my backyard!’ until Max Yasgur, another NYC-transplant who happened to be a conservative Republican, saw the desperate fest as a money-making scheme for a bad farming year. Keep in mind that these last-minute headaches would echo right up to this year in the stories about Woodstock 50 and how this was a plus since it linked the recent would-be fest to. Many articles this year about Woodstock 50 also pointed to the string of failed permits and Department of Health hurdles in 1969 and must have given Lang courage and ammo to carry on this year, as if to say “Hey, we did it before at the last minute!”

Let’s assume that you probably heard about what happened on Yasgur’s hay field with some half-million strangers, dozens of bands and a bunch of mud in the middle of August 1969. Much of what we remember about Woodstock 1969 though is clouded by ‘Golden Age’ thinking, which doesn’t recall all the problems. Together with a rainstorm (which made the Grateful Dead wonder if they’d get electrocuted on stage), the clogging of the New York State highway (which meant that acts had to be flown in by helicopter), the ticketed fest got overrun with moochers which necessitated turning the whole thing into a free-bee (wanna bet that no one got a refund?). Mind you, because the builders had to scramble around the short time frame, fences around the area couldn’t be finished. So the producers had no choice but to turn it into a free fest or try to kick out thousands of fans, which wasn’t going to happen.

As such, the ‘free’ concert wasn’t the generous gesture that many thought it was but more an act of necessity. Since Lang and friends weren’t prepared to get over-run by the Woodstock Nation as it came to be, they also weren’t ready to feed the hordes so it took the combined efforts of the U.S. Army (oh, the irony of hippies getting saved by the military) and a local Jewish community center (aided by Bethel’s farmers) to make sure the muddy masses wouldn’t starve to death. Wavy Gravy and his Hog Farm also had to pitch in to feed the hordes and help many of the attendees come down from bad trips.

When the fest was overrun with thousands of medical problems, the US army had to step in again to save them. In another bit of odd historical connect, one of the food vendors would get burned down because the prices were too high. That would be seen again at Woodstock 1999 but in a much worse way. By the time that Hendrix stepped on the stage early on Monday morning to finish the fest, the rainstorm on Sunday and the upcoming work week had already cleared away most the crowd, who had to wait until the following year to see his mind-blowing set in the theaters.

There were career-defining performances by Hendrix, Sly Stone, Santana, and the Who (though they hated their appearance). But there were also less-than-stellar performances from some of the big names such the Dead (who were more lit than usual), Janis Joplin, the Band, and Jefferson Airplane, which were purposely not circulated for posterity until years or decades later. Neil Young loved the mass there but hated the filming and (in)famously cut himself out of the movie. Just this year, some of the bands claimed that they don’t even remember if they actually got paid for W69.

So how and why did this giant mess turn into a piece of cultural/music history? 1967’s Monterey Pop Festival (which also had a stellar multi-day line-up, ground-breaking performances, and a movie) made W69 possible. But Monterey was done on a relatively smaller scale (less than half the size of Woodstock) and lacked some of the hippie vibes as the Monterey crowd was in seats and not rolling in the mud. The sheer size of the Bethel crowd that descended on Yasgur’s locale, which was unprecedented and unforeseen, made it a newsworthy event. Also, a little-known underground/indie Akron, Ohio filmmaker decided to show up there too and film the whole fest.


Picture taken on 17 August 1969 at the Woodstock Music and Art Fair. Photo: Woodstock Whisperer / Wikimedia Commons.

Michael Wadleigh shot over 100 miles of film, used the editing skills of a young Martin Scorsese among others and came up with an Academy Award-winning documentary that only got him a small slice of the financial pie. Afterward, he would have only one other non-Woodstock-related film to his credit after that. But that March 1970 film was enough to help create the legend of the festival, in part because it focused on the highlights and slices of counterculture life going on there while avoiding the rain/mud exodus, brown acid, and encapsulating it all into an exhilarating 185 minutes of celluloid.

Timing also worked in Woodstock 1969’s favor as it conveniently fell at the end of a decade, which made it easier for sociologists and historians to say that it closed the book on the hippie area. Pretty soon, it became clear that the 1970s weren’t going to be a continuation of the free-wheeling late 1960s. As Hunter S. Thompson chronicled in
Fear and Loathing in Las Vegas, a high-water mark for counter-cultural had already crested and was gone. That was particularly unsettling since he was writing about the demise of the hippie dream in 1971, making an event like Woodstock seem like a last gasp or last hurrah of the movement (even if subsequent legions of Deadheads and jam-band fans didn’t get the message).

And sure, there were bigger shows. Summer Jam (1973) at Watkins Glen drew 600,000 to see the Dead, Allmans and the Band). Other multi-day generational festivals like the Newport Folk Festival and US Fest occurred, but none of them had the cultural cache of Woodstock, all of which let the festival and its organizers reigned like legends for years. The name “Woodstock’ became so synonymous with the idea of a great festival that many subsequent fests took the end part of its name to latch on to its cultural significance. Anything called ‘stock’ was optimistically seen as an important big festival too. There is a poster-fest called Flatstock and the recently revived Wigstock. This year alone, you can attend Weedstock, Soupstock, and Foodstock. You can thank Lang and friends for all of these if you like.

Producer Michael Lang wasn’t just some idealistic hippie. Like any concert producer, he was a bit of hustler who then made loads of mistakes and happened to luck out with the 1969 fest. Ultimately, Lang’s problem turned out to be that he believed his own hype. Though he wasn’t on the level of Fyre Festivals’s Billy McFarland, Lang’s many gaffes would be vindicated by the mass invasion of hippies there who didn’t get into any scuffles, the film, and the mythologizing March 1970 hit from Crosby, Stills and Nash about the fest. That all turned his baby into a zeitgeist-defining cultural phenom, which continues to be mythologized through a recent PBS documentary.


But Woodstock also had a sadder, pathetic legacy attached to it which began right after Hendrix finished his set there. Yasgur was asked for a 1970 encore of the fest and said ‘no thanks’, having to put up with the acrimony and lawsuits from his neighbors for making such a mess of the area. Though he was unapologetic about the 1969 show, he would sell the farm in 1971, move to Florida and die there less than two years later. The local farmers also went after the festival with years of lawsuits dragging out for most of the Me Decade. Thanks in part to the legal woes, Lang and friends weren’t able to keep the fest going or make it a yearly event, which could have capitalized on the success of the movie and kept the momentum of the name and brand going right away as Glastonbury and the New Orleans Jazz and Heritage Festival would (both starting up in 1970). Having a yearly fest might have also helped Woodstock Enterprises plan better instead of having a long history of subsequent screw-ups.

When 1979 came around, the Enterprises finally had the snappy notion to revival their old festival at a time when other festivals weren’t even coming close to gaining the cache of their little 1969 show. But even then, they still couldn’t capitalize on their own dumb luck. To start with, doo-wop promoter Richard Nader had his own bright idea to stage a ‘Woodstock Reunion’ on Long Island, with a crowd of 18,000 there to see 1969 alumni like Paul Butterfield, John Sebastian, and Johnny Winter, though in true Woodstock fashion, there were plenty of organizational flubs. The Enterprise held its own 10-year-anniversary at Madison Square Garden instead of upstate New York, including a bunch of the same performers as the Nader show. That just added to the confusion of having two anniversary shows in the same area around the same time. There is a VHS video of the MSG show which came out in 1991 floating around if you can find it, but hopefully, you have other priorities.


When 20th anniversary time came up in 1989, Woodstock Enterprises did nothing. But something interesting happened regardless and with no help from them. A bunch of freaks decided to put on their own free-for-all fest at the original site, featuring mostly local bands but eventually ballooning into, supposedly, a six-figure crowd to witness it, leading to spots on Good Morning America. There’s some video floating around to document ‘the Forgotten Woodstock’, but it deserves more than a Wikipedia entry to cover it. The 1989 fest seemed in many ways truer to the communal spirit of the 1969 fest than anything that the Enterprises put on afterward or maybe even more than the original fest itself.

Compared to all of its other revivals, you could make the case that when the Enterprises finally did roll up its sleeves to make another fest, their next concert series was more successful than all its other later flops. Taking place in Saugerties, New York (one hour north of Bethel), Woodstock 1994, aka Mud-Stock, was also plagued by weather problems. But it wisely took a multi-generational approach, booking not just 1969 vets like Joe Cocker, Country Joe, Santana, CSN, and the ubiquitous John Sebastian but also Aphex Twin (as part of its ‘Ravestock’ stage), Primus, Peter Gabriel, Nine Inch Nails, Metallica, Gil Scott-Heron, Jimmy Cliff, the Neville Brothers, Cypress Hill, Aerosmith, and in the biggest coup considering his opposition to the 1969 concert, Bob Dylan. Oh, and it was a break-out moment for Green Day.

To keep it as part of the tradition, there were plenty of logistical screw-ups, and the crowd size overwhelmed the promoters. Though it wasn’t a generational epoch like the original, the line-up was pretty impressive, and no major incidents happened. Plus, it seemed like people enjoyed it and it got some good write-ups, even if Billie Joe Armstrong’s mom didn’t like the scene. Even if the New York Times thought it was a ridiculous mess, at least the shows didn’t disgrace the brand name.


The same couldn’t be said of Woodstock 1999. Situated on an Air Force base in Rome, New York (just west of Syracuse), the promoters had beefed up fencing and security in place, but they still weren’t ready for what would be unleashed there. Another impressive, diverse round-up of performers were there including George Clinton & P-Funk, the Roots, the Chemical Brothers, Sheryl Crow, Elvis Costello, Willie Nelson, Alanis Morissette, Ice Cube, Los Lobos, and a notable lack of 1969 vets. But the sweltering heat, high drink/food prices didn’t help the tense vibes there. Fred Durst of Limp Bizkit egged the crowd on to tear down walls (literally, which kind of is a hippie thing to do). What was meant as a candle-lit vigil for gun violence during the Red Hot Chili Peppers’ set turned into multiple out-of-control bonfires. Even worse, there were multiple reports of rape and death and subsequent lawsuits from the show. With good reason, the press had a field day saying that it was “the day the music died”. A little dramatic but remember that all of this happened under the banner of ‘Woodstock.’

Even without the disaster of the 1999 fest, by this time, Woodstock Enterprises also became a victim of its own eventual cultural success and lost some of its unique quality as many other festivals took up the idea of massive multi-day gatherings. There was the much more successful Coachella, also started that year, SXSW (which started in 1987 but didn’t gain momentum until the 1990s) and Lollapalooza, which would debut in 1991. Like Woodstock, Perry Ferrell’s Lollapalooza creation became a generational phenom which, like the 1994 and 1999 Woodstock shows, combined a diverse, grand set of talent. Since the first few years of Lolla pre-dated Woodstock 1994, you could argue that Enterprises took a page from the Lolla playbook for Woodstock 1994. Also, like Woodstock, Lollapalooza became such a cultural mainstay that as a mark of its success, the name brand is used by other fests to glom onto in hopes of their own success. Right now, you can attend Wallypalooza, Curl Palooza, Grunge-A-Palooza, and even Philly’s Wine Shine ‘n Pierogi Palooza. With all of Woodstock’s later-day flops, you can expect to hear more festivals with the ‘Palooza’ name than the ‘Stock’ name in the future.

Determined that their 1999 horror show shouldn’t stop the party, Woodstock Enterprises came crawling back in 2009 with the idea to make a tour out of their brand with their ‘Heroes of Woodstock Tour’. Because of the whole 2019 fiasco, it is the last concert series that they’ve done so far. With stops at casinos, fairgrounds, a winery and the original Bethel site, the ‘Heroes’ were Jefferson Starship, Big Brother and the Holding Company (obviously minus Janis), Canned Heat (with its three pivotal members from its late 1960s/early 1970s line-up all deceased by then), Country Joe McDonald, Ten Years After (without its charismatic singer Alvin Lee), Tom Constanten (who was briefly in the Dead in the late 1960s) and of course John Sebastian. Sorry, but an online search doesn’t turn up any reviews or videos of this but judging by the talent, maybe you didn’t miss much and it probably would have worked better as an extended comedy sketch like National Lampoon’s Lemmings or an episode of Flight of the Conchords. Granted, it’s not the kind of thing that you can extend a legacy on but it wasn’t the disaster that 1999 was.

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Read part 2: Woodstock 50’s Doom and Gloom: Caught in a Devil’s Bargain

Read part 3: Woodstock 50’s Cautionary Example: Memories of a Cancelled Free Festival