Even though the new millennium had yet to arrive, pop icon Madonna was already kick-starting a personal and professional vibe shift. In 1996, she surprised and delighted audiences with her starring turn in big-screen feature Evita, earning the singer her first Oscar when she took the prize for Best Original Song (“You Must Love Me”) at the 69th Academy Awards in March 1997.

It was the summer of ’97 when Madonna hit the recording studio with electronic artist William Orbit to make her next original album, the proper follow-up to 1994 full-length, Bedtime Stories: seventh studio LP, Ray of Light.

“I look at more musical chances. I let William [Orbit] play Mad professor,” Madge told SPIN in 1998. “He comes from a very experimental, cutting-edge sort of place — he’s not a trained musician, and I’m used to working with classically trained musicians — but I knew that’s where I wanted to go,so I took a lot more risks. Oftentimes the creative process was frustrating because I wasn’t used to it; it took a lot longer than usual to make this record. But I realize now that I need that time to get where I was going.”

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