Following Bedtime Stories, Madonna waited four years to release her next studio album, the longest span between new records in her career to that point.
During that time, she starred in Evita, gave birth to daughter Lourdes, and found religion in the form of the Jewish mystical tradition of Kabbalah. Busy, busy!
The Evita role prompted her to work with a vocal coach, a decision that paid off on 1998’s Ray of Light.
Madonna suffered a fair amount of backlash after her Sex book and Erotica album were deemed offensive by the pearl-clutchers. A controversial appearance on Late Show with David Letterman, heavily censored due to profanity and subject matter, didn’t help.
As a result, 1994’s Bedtime Stories was positioned as a mea culpa. In a promotional video, she promised “no sexual references” on the new album, and a return to the “innocent” Madonna of the past. Holding her co-writer’s daughter on her lap, she promised to be a “good girl.”
Madonna capped off her historic 80s run with the 1990 release of The Immaculate Collection, a greatest hits compilation that spanned her first four albums plus various contributions to movie soundtracks. The album sold more than 10 million copies in the U.S. and 30 million worldwide, making it her top-selling release.
Madonna started her new chapter by creating Maverick, a multimedia company with divisions dedicated to music, TV/film and book publishing. She released the steel-cover photo book Sex, which featured nude images of her and a rotating cast of partners both famous and unknown.
Madonna hit a rough patch between the release of the smash hit True Blue in 1986 and her next album, 1989’s Like a Prayer.
Her marriage to Sean Penn fell apart in ugly fashion, amid rumors of his jealousy driving him to acts of violence against Madonna and others. She has since denied those reports, though she provided the police with vivid details at the time and the stories were corroborated by witnesses.
Most iconic artists have the one album that cemented their status, breaking sales records and establishing their chokehold on the culture.
Michael Jackson had Thriller. U2 had The Joshua Tree. Prince had Purple Rain.
Madonna, arguably, had two such albums. Two years after Like a Virgin became a global smash and the top-selling album by a woman, she dropped True Blue in 1986 and managed to top herself.
Meet Me In Montauk 