Merci, Madame

Madonna reasserts her relevance and unpredictability.

- Craig Jenkins

WE HONOR THE first 20 years of music legends’ careers for the drive that elevates them from anonymity to celebrity and the vision that keeps them in flight throughout the best years. We spend the next 20 years weaponizing their own standards against them, calling each album a “radical departure” or a “return to form,” or else quietly losing interest in everything but the classics. There’s more love for “Taxman” and “Drive My Car” than “Say Say Say” or “Got My Mind Set on You.” People want to remember their favorite figures at their best, but the miscalculations and recalibrations that happen afterward are just as integral to the story of a brilliant career as the moves made at the artists’ peak.

Madonna Ciccone moved to New York City from Michigan at the age of 19 in the late ’70s with a dream of making it in showbiz. In five years, she maneuvered through the eclectic scene at the lower-Manhattan nightclub Danceteria and pieced together a demo, which a resident DJ then ran up the pipeline to the label heads who released her early singles and self-titled debut album. In ten years, Madonna was a pop star with a dozen international hit records, anxiously setting her sights on a lasting film career. By year 20, she’d scored a Golden Globe for Best Actress in a Motion Picture (for Evita), written a New York Times best seller, and topped the charts again with a studio album recounting everything she’d learned as a new mother and a student of Eastern mysticism and European dance music.

If you’re the kind of fan who learns by scrubbing lists of the best of things, you might see Ray of Light as the last essential Madonna album (or hang around till 2000’s exquisite