In November 1999, at a time when he was routinely referred to as "the Artist Formerly Known as Prince," with his signature glyph doubling as his name, Prince released the LP Rave Un2 the Joy Fantastic. The album featured guest appearances from Chuck D, Eve, Gwen Stefani and Ani DiFranco. There was also a dual contribution from the pop artist who would soon branch out into country music, Sheryl Crow. The pair sang together on the album's "Baby Knows," and the disc also included Prince's version of Crow's 1996 hit "Everyday Is a Winding Road."
Throughout 1999, Crow was a featured performer on the groundbreaking Lilith Fair Tour. Organized by singer Sarah McLachlan, the festival dates consisted of three stages and dozens of female acts, including a strong country presence with the Dixie Chicks, Martina McBride, Shawn Colvin, Patty Griffin and Kelly Willis appearing at various venues. By the time Lilith Fair hit Toronto in August, with just a handful of dates remaining, Crow had jammed with Bob Dylan, the Pretenders' Chrissie Hynde and Eric Clapton, not to mention Willie Nelson and June Carter Cash.
In the above clip, from the second of the tour's two-night stint in Toronto on August 22nd, Crow hit the stage in a vintage David Bowie T-shirt and black leather skirt, dancing throughout the intro to "Everyday Is a Winding Road," with Prince casually strolling up next to her onstage. Decked out in purple and playing a royal blue guitar, the Artist added backing vocals during the song's chorus, giving the light rocker a funkier, more bluesy edge. Crow's vocal lines, especially in the song's second verse, are echoed by Prince's guitar riffs, and he follows that with a fiery, string-bending solo.
After putting his arm around her and encouraging the crowd to "give it up" for Crow, she follows suit, referring to him as "the Artist Formerly Known As…" without adding his former (and future) name. As the Artist walks offstage, Crow and band continue the song for another minute, leaving concertgoers with a memory than has no doubt been recalled more frequently in recent days, in light of Prince's passing on Thursday, April 21st.
In a CNN interview the following day, Crow, who toured with Michael Jackson in the late Eighties, said, "I can remember thinking, 'Oh, I'd give anything to be in his band, just to learn from the greatest.'"