While it's true that Prince's use of cover songs has occasionally been known send mixed messages, more often than not the gesture ought to be interpreted as artistic merit's highest affirmation.

The latter was the case when Prince poached Sheryl Crow's 1996 hit "Everyday Is a Winding Road" for his 1999 album Rave Un2 the Joy Fantastic. In the months leading up to its release, Prince could hardly keep himself away from the song, making appearances on the Lilith Fair festival tour to perform it alongside Crow.

"I never play that song where I don't get to the end of it and hear [Prince] in my ear go, 'Sheryl Crow, y'all,'" Crow told Howard Stern in an interview, referring to Prince's vocal ad-libbing at the end of a Lilith Fair duet. The mutual admiration was the beginning of what would be a lasting friendship between the two. But the incorporation of her song also served a practical purpose as well.

Despite its ecstasy-promising title, the release of Rave Un2 the Joy Fantastic found Prince taming his sound. After offering a more soulful and jazzier approach on his previous album The Vault: Old Friends 4 Sale—released just three months prior—Prince sought to forge an accessible collection of hits that could retrieve his pop chart compatibility. To achieve this, the album was decorated with guest features from commercial artists such as Gwen Stefani ("So Far, So Pleased") and Chuck D ("Undisputed"). Sheryl Crow guested on "Baby Knows," a sexed-up track that found Crow out of her musical element and locked into Prince's.

To Crow, the session would feed the peculiarity of Prince, whose lyrical debauchery seemed almost comically out of balance to his solemn religious faith.

"It just kind of struck me because he was a mystery to everyone," Crow would recall a year after Prince's passing.

Hear Prince Perform "Everyday is a Winding Road"

"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."

But the sexual imagery wasn't just a vital illustrative device that animates the Prince songbook—it's also one he'd sneak into others'. The vending machine repair man Sheryl Crow hitches a ride with in "Everyday Is a Winding Road" is replaced with a Crazy Horse showgirl.

While Prince didn't embark on a full tour to accompany Rave Un2 the Joy Fantastic—a rare move—the scattershot performances that spanned 1999 frequently included the cover. But the inspiration flowing between the two persisted well beyond 1999. Just earlier this year, Sheryl Crow spoke to Music Choice TV about how thinking about Prince after his death influenced "Grow Up," a song from her 2017 album Be Myself.

"I would turn on the news and see all this glorious footage of Prince in his element, with that child-like innocence about music," she said. "I started feeling like, 'Man, I want that ... innocent love of making music and having a repartee or exchange with fans and the audience.' And so we wrote this song called, 'I Don't Want to Grow Up.'"