People say that the thing that makes Madonna such a brilliant, vital artist is that she has stayed fresh over the course of 30 years of pop music by constantly reinventing herself. While that may be true, there's another layer to her that is often overlooked: She does an incredible job of constantly couching herself as an underdog. Because of her constant risk taking and experimentation, each of her albums seems like a comeback effort (even though she's never really gone away).
The best example of this came in 1998, when on this day she released Ray of Light. The middle part of the 1990s were unusually rocky for Madonna, as she focused a lot of her energy on the somewhat-maligned film version of the musical "Evita" (in which she played Eva Peron). Her last pop album was 1994's Bedtime Stories, a more straight-ahead R&B album that saw her attempting to transition from her Erotica persona into something different (though the ill-defined goals of that album make it sound unfocused today). With the word "electronica" on the lips of music aficionados around the world and albums by the Prodigy topping the Billboard album chart, Madonna tapped dance music maven William Orbit to guide Ray of Light. The result deftly melds Madonna's traditional pop and R&B sounds with bits of techno, trip-hop, house and trance.
Despite the fact that the lead single was the extremely odd "Frozen," Ray of Light became one of Madonna's biggest albums, spawning hits like "The Power of Goodbye" and "Drowned World (Substitute for Love)." But no doubt the biggest hit was the title track, which remains one of the finest radio singles of the '90s and whose clip scored a VMA for Video of the Year in 1998.