It was billed as the musical event of the summer, a chance to remember a defining moment of the counterculture movement that took place in a field in upstate New York half a century ago.

But just three months away from Woodstock 50, at which Jay-Z, The Killers and Miley Cyrus are supposed to be performing, plans are in disarray as event organisers battle their financial backers in a extensive series of court challenges.

The event, which is due to be held 150 miles from the original site for three days in the middle of August, has been in jeopardy ever since the Japanese advertising and marketing giant Dentsu Aegis pulled the plug on $30m of backing in April.

A series of subsequent court orders first found that Dentsu Aegis did not have the right to cancel the event, and subsequently that festival organisers could not stop their former financial backer from being involved in the planning the event.

If nothing else, the legal dramas played out in court are in the spirit of Woodstock’s previous incarnations in 1969, 1994 and 1999, marked respectively by love, mud and violence.

But Marc Kasowitz, lawyer for Woodstock 50’s organiser Michael Lang, told the Poughkeepsie Journal last week: “Woodstock will prevail.”

There’s little certainty it will, however, despite new financing, and tickets have yet to go on sale.

Meanwhile, after a series of organisational changes and conceptual rethinks, a small-scale festival to be held at the original site of the 1969 Woodstock Music and Art Fair in Bethel, New York, appears to be going ahead, with Ringo Starr, Santana and John Fogerty headlining.

But as each event battles to rekindle the spirit of 69, the tribulations of both have become something of a standing joke in the music industry.

“The original Woodstock was an envelope-pushing revolution that captured a national zeitgeist the major media had missed. Woodstock 50 is just a me-too event,” wrote the music industry blogger Bob Lefsetz.

Lefsetz goes on to describe Woodstock 50 as “the Fyre Festival in reverse”, referring to the ill-fated concert event in the Bahamas that collapsed, stranding ticket holders, and ultimately saw organiser Billy Macfarland jailed for fraud.

The crowd braves the rain at the original Woodstock festival in Bethel, New York in August 1969. Photograph: Elliott Landy/AFP/Getty Images

Lefsetz went further, describing the concept of Woodstock 50 as “like coming up with a new gas-guzzling sedan in not only the age of SUVs, but electric cars.” Organisers would have been better off, he said, promoting the original acts, from Mountain to Crosby, Stills, Nash & Young to Arlo Guthrie, and have contemporary figures such as Gary Clark Jr standing in for Jimi Hendrix.

“If you expect peace and love to reign in a field at Watkins Glen [site of the venue] you’re delusional. So expect Woodstock 50 to be a blip in history,” said Lesfetz

Efforts to revive Woodstock at 50 have also been hit by the broader failure of the music industry to create bands that can headline multi-act festivals while established acts have burned their audiences by playing the circuit too often.

Several festivals, including the Tennessee-based Bonnaroo, are said to be struggling. But Woodstock remains a case in point, attracting widespread criticism for cynically mining hippie-era, feelgood sentiments that would have been better left unexploited. Older concertgoers don’t want to camp, and don’t want to subsist on hot dogs and french fries.

“Who wants to camp to see Jay-Z?” says rock manager Andy Gershon, who recently staged a sold-out, seven-night run of Morrissey shows on Broadway in New York.

“Coachella is this generation’s Woodstock, and nobody cares about Woodstock 50 among the festival crowd in 2019.”

But Lang, who promoted the original Woodstock, remains unbowed. He told the New York Times last month, the chaos “kind of fits the legacy of Woodstock in a way”.

“In 1969, we got kicked out of [the town of] Wallkill a month before the festival was to happen. One of the miracles was that we found a site the next day.” Lang said there was no other solution besides commitment. “We were committed then, and we’re not stopping now.”

• This article was amended on 4 June 2019 to clarify the description of Dentsu Aegis.