Late last year, Michael Lang, one of the producers of the original Woodstock festival in 1969, began to approach music’s most powerful managers and booking agents with a pitch.

Lang wanted to commemorate Woodstock’s 50th anniversary with a three-day, multigenerational event that would draw 150,000 people to a Formula One racetrack in upstate New York. With the Woodstock brand as a magnet, he told them, the festival would celebrate the spirit of the original yet be relevant to the youth of today, according to five agents and other talent representatives, who spoke anonymously because the conversations were confidential.

The agents were skeptical.

With less than a year before Lang’s chosen weekend, Aug. 16 to 18, time was short. They doubted whether the Woodstock name meant much to Generation Z. And how would Woodstock 50 stand out from the glut of festivals already flooding the market?

Still, the agencies agreed to supply top-tier talent to the festival — if Lang and his partners accepted all the risk. As one senior agent recalled their message to him: “We’ll help. But you’re going to overpay us, and pay us up front.”