When Sheryl Crow first hit the solo big time, she was trailed by the interesting fact that she’d been one of Michael Jackson’s backup singers (on “Billie Jean” and on tour). Crow’s “Every Day is a Winding Road” musical style didn’t immediately bring to mind Mr. Thriller, so the story lent Crow’s ascent extra intrigue and cemented the idea of her as a versatile, in-demand performer.
Later Crow got to work with Prince, who actually covered “Every Day is a Winding Road” — he liked it so much. So Crow has a resume that includes having worked with perhaps the two foremost pop music geniuses in history, both tragically gone too young. Sheryl Crow tells Howard Stern about singing and touring with Michael Jackson and about her relationship with Prince in the clips below. Howard Stern, as usual, gets the best out of his guests.