
Following the soft performance of "Erotica" and having done a little damage control with "Bedtime Stories", Madonna experienced a major rebranding when she starred in the film "Evita" (Madonna won Golden Globe Award for Best Actress in Motion Picture Musical or Comedy for "Evita") During this time, the public saw Madonna in new ways, and Madonna saw herself in new ways, mostly thanks to becoming a mother and to her study of Kabbalah.
Long story short: Guy Oseary (her future manager) suggested Madonna to work with William Orbit. She loved his sound, and she loved the idea of making electronica that had substantial lyrics. Collaborating with the British electro composer/ producer William Orbit reaffirmed her reputation as a savvy musical regenerator.
5 singles were released from Ray Of Light, and they were all very different.
- FROZEN
The blue-tinted video opens with the camera traveling across the desolate landscape, finding Madonna - witchy and alone - levitating above the parched earth while the wind wreaks havoc with her long locks and flowing wardrobe. The first of several visually shocking statements occurs when Madonna appears to fall over, shattering into a flock of black birds. Immediately thereafter, Madonna appears in triplicate, singing with herself, a compelling representation of the multiple sides to her personality that have struggled to stay at the fore of her career. Next, her form transforms into a running dog, continuing a theme of transformations. and of a startlingly simple connectivity with the natural world. The illusion that Madonna has extra arms as she performs Hindu movements underscores the video's mystical vibe. Shot in the Mojave Desert, Frozen is consistently ranked among Madonna's most innovative music videos.
Best live performance
- RAY OF LIGHT
Ray of light was shot over the course of 14 days. The clip was made up of time-lapse scenes of a sun rising, people going about their day, the subway system, kid's playtime at a school, traffic and other daily events, with an artificially tanned Madonna superimposed over them. Toward the end, Madonna danced rapturously on a lighted disco floor in her wifebeater, looking sexy as hell and freer than she'd ever looked on film.
Best live performance
"this performance gave us an iconic dancing Oprah gif"

- DROWNED WORLD/SUBSTITUTE FOR LOVE
Ballad about the emptiness of fame.
The intimate atmospheric video for one of Madonna's most personal singles begins with her character having to rush through a crush of paparazzi. As she driven away in her car, they pursue her, their flashes illuminating her in the back seat. The scene, so soon after the death of Princess Diana, was clearly intended to remind viewers of that tragedy, through Madonna had experienced the same sort of scene many times in her own life. She was point blank accused of "exploiting" Diana's death.
Best live performance
- THE POWER OF GOOD BYE
Madonna's look for the video is unlike her look for any other - she's with a dark hair and a smokey eye and in shot through a blue gel that seems to imply submerision and also depression. By the end of the video Madonna walks along the beach, apparently to commit suicide in the waves. The hyper real beach scenes are straight out of the Joan Crawford film "Humoresque" (1946)
Best live performance
- NOTHING REALLY MATTERS
The music video for Nothing Really Matters was one of several items in Madonna's career that was inspired by the novel "Memoirs of a Geisha" (1997) Madonna cast herself as a figure similar to the book's villainous (but fabulous) Hatsumomo. Through the video was inspired by the historical novel, its vibe is breathtakingly avant-garde. Madonna, in geisha garb, cradles a plastic bag filled with fluid, and her Japanese extras spasm in eerie ways, as if the cast of a hard-to-explain nightmare. Madonna performs the song in a red kimono, dancing jerkily in a way that can only be likened to the moves displayed by Elaine Benes (Julia-Louis Dreyfus) on the famous Seinfeld (1989-1998) episode "The little kicks". The video is disturbing to watch, summoning images of involuntary confinement in a surreal asylum setting. Madonna's mood, at first serious, degenerates into frivolity...or is it hysteria? The video is a moment from Madonna's career that is usually cited by critics who accuse her of cultural appropriation.
Best live performance
Aftermath

Ray Of light set the record for biggest first-week sales by a female artist in Nielsen SoundScan era at that time with 371,000 copies sold. So far the album sold over 16 million copies and most fans call it her best work (OP included)
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Mods - it's the Original ONTD post, I spent like hours making it. Hope it makes the cut!