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After the release of  The Immaculate Collection featuring the biggest and most iconic hits of Madonna's repertoire from the 80s through 1990 — it became clear she was on a different trajectory with her music.



Final hits like "Vogue" and "Rescue Me" showed her not only embracing the underground House Music movement of the late 80s but bringing it mainstream — while "Justify My Love" employed the underground sub-genre Trip-Hop.



These musical styles were subsequently employed to greater effect in subsequent releases, which ultimately led to the album often considered the pinnacle of her career "Ray Of Light," which leaned heavily towards the exploding Trance sound with a dash of psychedelia while retaining its pop sensibilities. There was no genre that Madonna wasn't willing to dabble in and deliver with mass appeal.



The 1990s through 2001 featured Madonna's most ambitious musical output as her live concerts had already turned into masterful art shows since "The Blonde Ambition Tour" making her the most profitable marketing machine and performer of the 20th and 21st century — literally. These performances have often been imitated (se...