Lilith Fair was one of the most successful touring festivals of the late ‘90s, routinely playing to massive crowds thanks to its impressive lineup of female artists. One of its biggest stars was Sheryl Crow, the multi-platinum singer-songwriter who dominated radio and sales charts in the latter half of the decade. On Aug. 22, 1999 Lilith Fair played its second night in Toronto. A special guest joined Crow on stage that evening, Prince.

The surprise appearance was initially delivered with little fanfare and no formal introduction from Crow, meaning it took the crowd a little bit to realize what was going on. But the rising waves of applause show they figured it out soon enough. As Crow launched into her hit single “Everyday is a Winding Road," the Artist Formerly Known as Prince (as he was then called), simply strutted his way to center stage and began playing guitar.

Prince was very familiar with the song. At this point, he’d already recorded a cover version for Rave Un2 the Joy Fantastic, however that album wouldn’t be released until several months later.

During his Toronto appearance, the legendary musician delivered a blues-rock edge to the originally poppy track, adding wailing guitar and backing vocals. Arguably the biggest highlight of the performance came after the song’s second verse, when Crow stepped back and allowed the purple-draped icon to do his thing. Prince launched into a blistering guitar solo, jamming with the backing band before rejoining Crow for the chorus.

Rave Un2 the Joy Fantastic would come out that November with the cover of “Everyday is a Winding Road” (and another Crow / Prince collaboration entitled "Baby Knows") among its tracks. In a 2017 radio interview, Crow recalled hearing Prince’s version of her song.

"It was kind of funny because he changed the last verse -- the lyrics," the singer remembered. "'I've been swimming in a sea of anarchy / I've been living on coffee and nicotine.' And he changed it to 'I've been living on [compliments] and herbal tea.'"

"It just kind of struck me because he was a mystery to everyone. He had this kind of sexual image, but he also had this profound humility when it came to God -- like he was a very spiritual person. But I loved him. I loved how youthful he was in his love for what he did."

“I think the world at large was really impacted by his death,” Crow later recalled in an interview with Music Choice. “But for me because I knew him and I hadn’t seen him in a long time and just reading about his struggle, of course I had that knee jerk, 'Oh I wish I’d stayed in touch with him. I wish I’d reached out to him.'”

Though he had lost touch with Crow by the time of his death, Prince’s passing inspired the pop star to write the song “Grow Up” for her 2017 LP Be Myself.

“I would turn on the news and I would see all this glorious footage of Prince in his element and just with that childlike innocence about music,” the singer explained. “I started feeling like, ‘Man, I want that.’” Crow went on to admit that Prince’s influence on the track extended beyond the lyrics. “When you listen to it, there are some Prince harmonies that are kind of like (kisses towards heaven).”

 

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