Prince and “begging” seem to be two contradictory ideas, but as Lilith Fair: Building a Mystery—The Untold Story reveals, there was one festival that the rock icon wanted to play so badly he was willing to ask again and again (and again). The “Purple Rain” singer reportedly asked the women-centered traveling music festival for a spot on the bill multiple times.
Videos by American Songwriter
Lilith Fair was famously a woman-centered, traveling musical event. Still, that distinction didn’t stop Prince from wanting to be included. But each time, his requests proved too demanding for the equity-minded event to accommodate.
The only way he would get on that bill was with a little bit of compromise (and with a little help from a female friend).
Prince Reportedly “Begged” To Be a Part of This Festival
Prince’s androgynous identity made him an understandable fit for the late 1990s phenomenon that was the Lilith Fair festival. But his rider proved too difficult for the organizers to entertain. While researching the festival for her 2025 documentary, filmmaker Ally Pankiw discovered that Prince “begged” to be on the bill “year after year,” per People. “He had really outsized requests. Lilith Fair was very equitable. Everyone had the same size dressing room, and no one had this crazy rider.”
“Everyone got the same amount of stage time,” she continued. “Things were very collaborative and equal, and his demands didn’t match that.” After realizing that the festival wasn’t going to budge on his demands, the singer acquiesced.
“He was like, ‘Fine, I don’t need any of that. I just want to come play Lilith,’” Pankiw said. “I think that was surprising, just how mainstream and cool it was, and that people who actually worked in music understood its value and how cool the performers and the artists were there.”
Prince finally got his wish when he made a guest appearance during Sheryl Crow’s set at a festival stop in Toronto on August 22, 1999. The pair sang “Everyday Is a Winding Road”, Crow’s hit from three years earlier, to the audience’s great delight.
It was a long-awaited dream for Prince and Crow. “I’ve never been around anyone like that,” Crow later said of Prince. “That was so innately gifted. You just couldn’t explain how great he was. He could play like McCoy Tyner, he could play like Oscar Peterson, he could pick up the guitar and play like Hendrix. He could play the bass like James Jamerson. The guy was just gifted. A nice person, childlike in his enthusiasm for things.”
Including, apparently, Lilith Fair.
Photo by Kai-Uwe Wärner/picture alliance via Getty Images
Leave a Reply
Only members can comment. Become a member. Already a member? Log in.