Things were not looking good for the music festival. A month out, the organizers had lost their permit and were scrambling to find another location. In the scramble, the organizers couldn’t get everything ready in time. When the festival-goers poured in, there weren’t enough toilets or medical facilities, and there certainly wasn’t enough food or water. To top it off, the festival grounds were hot, humid, rainy and muddy.

No, this wasn’t Fyre Festival. This was the original Woodstock Music and Art Fair in August 1969. And although it’s become America’s most iconic music festival, “it probably should’ve been a disaster,” says Joel Makower, author of Woodstock: The Oral History. “The fact that it came off as well as it did is a minor miracle.”

Woodstock didn’t boast the same kind of star-studded lineup that you might see at major festivals today—though some of those acts later became legendary. Many of the “major commercial groups of that particular time period really were not at Woodstock,” says James Perone, author of Woodstock: An Encyclopedia of the Music and Art Fair.

While the festival did book nationally popular acts like Jimi Hendrix, The Who and Sly and the Family Stone, Perone says there were “only maybe half a dozen or so that really had a lot of popular hits around that particular time.” In hindsight, the concert featured many of the biggest names in music history. But you can’t plan to invite lesser-known bands who will become famous later, and the fact that Woodstock accidentally did has added to its mystique.

The whole event was chaotic from beginning to end. So many people flooded into the festival grounds that the promoters had to stop checking tickets and just make the concert free because they were too overwhelmed. Nearly half a million people descended on the festival grounds in Bethel, New York, backing up the roads for miles and making some of the musical acts late.

Richie Havens, who wasn’t scheduled to open the festival, ended up having to play its first three hours because so many people were running late. When he ran out of songs to play, he famously improvised one called “Freedom.”

“The conditions were suboptimal to say the least,” Makower says. “There were electrical wires going under the mud and the ground was vibrating.” The stage wasn’t well-protected from the rain, and “everyone was praying that [the light towers] weren’t going to fall because they just weren’t well-tethered. And so the conditions for the acts to play were challenging.”

Not everyone thought they were able to meet the challenge. The Grateful Dead considered Woodstock one of the band’s “worst sets ever,” Makower says. And The Who’s lead singer Roger Daltrey has said that playing Woodstock was a miserable experience. In addition to waiting in traffic jams for hours, then waiting backstage for several more hours, Daltrey said there wasn’t any food backstage that wasn’t laced with LSD; and he accidentally dosed himself when he made a cup of tea before he went onstage.

“Looking out the gloom of Woodstock, making out the vague shape of half a million mud-caked people as the lights swept over them, I felt in my sleep-deprived, hallucinating state that this was my nightmare come true,” Daltrey wrote in his memoir, Thanks a Lot Mr. Kibblewhite. “The monitors kept breaking. The sound was sh**.”

So why is Woodstock remembered as the greatest rock concert ever? For starters, “it was definitely the launchpad for a number of acts,” Makower says. This was especially true if the acts were featured in the Woodstock documentary that Warner Brothers released several months after the festival. “A lot of people really lived Woodstock through the movie,” Makower says. “And so the movie influenced, I think, more people than the actual event.”

Carlos Santana’s band wasn’t very well-known before it played Woodstock and appeared in the film. Joe Cocker, too, became famous for his unusual singing movements and his unique cover of “With a Little Help From My Friends” that appeared in the documentary (his cover later became the theme song for The Wonder Years). Richie Havens’ opening act, also captured in the film, expanded his audience beyond the folk scene.

In addition, Woodstock was one of the first concerts at which Crosby, Stills, Nash and Young played together as a group. In one memorable part of the concert and the documentary, Stephen Stills tells the crowd: “This is the second time we've ever played in front of people, man. We're scared sh**less.”

Both Makower and Perone say that, for many of the festival-goers, the music wasn’t the most important part of Woodstock—it was the general atmosphere that made it memorable. That’s not to say that everything was perfect. There were plenty of people who had a bad time or a bad trip, as well as one person who died of a drug overdose and another who died from being run over by a tractor in his sleep. But despite Woodstock’s extremely poor conditions, the crowds remained relatively peaceful and nonviolent.

The fact that Woodstock was such a weird accident means it’s probably impossible to recreate, though many have tried. “If you look at Woodstock ‘94 or the 1999 festival, they ended up being entirely different,” Perone says. At the ‘99 festival in particular, violence broke out and attendees torched concession stands. “It seems like attempts to recreate that may have more big name performers, but just the entire atmosphere doesn’t seem to have been captured.”

In 2019, organizers attempted to give it one more try with Woodstock 50. The concert was set to feature a good number of performers from the original festival, including Santana, Melanie, David Crosby and Dead & Company (an outgrowth of The Grateful Dead). It was also going to feature Robert Plant, whose band Led Zeppelin was invited to play at the original Woodstock but turned it down on the advice of its manager.

But Woodstock 50 fell apart months before its August concert date. In April, organizers had to postpone ticket sales because they submitted their permit late and the New York State Department of Health hadn’t had time to approve it. A week later, the festival’s funder Dentsu Aegis Network abruptly announced it was canceling the festival because it couldn’t produce “an event worthy of the Woodstock Brand name while also ensuring the health and safety of the artists, partners and attendees.” Roger Daltrey would probably agree.