The good time 80s gal shifted gear towards more sophisticated, adult pop fare during this period and Dick Tracy brought out the naughty vaudeville gal in her. M took that to varying extremes on I'm Breathless - sometimes with a dash of class (He's A Man) and sometimes not (Hanky Panky).
She handled the Sondheim songs well on IB (the Oscar performance of Sooner or Later remains one of her greatest live performances and is an album standout here). If any album equipped her for her future role in Evita it was this one - not Something to Remember.
STR of course first came to life here, but with a wealth of choices, I'm going with I'm Going Bananas as the best non Sondheim/non-single here. Fun, fiesty - there's that Latin sound again - and brought to life best on stage (via 1993's Girlie Show tour).
Her fans love a bit of sugar with their M, but Erotica was
the bitter, straight up brew and one of her greatest achievements.
Erotica pushed the envelope and broke the rules preferring to experiment or change things up even when it was (rarely) on familiar ground (Rain's double vocal verse, Deeper and Deeper's WTF-did-that-flamenco-come-from moment).
Words and Where Life Begins were further examples of what thumbing one's nose at convention can achieve - but it was on Waiting that we got some thrilling New Jill swing and the sound byte "if you have to ask for something more than once or twice, it wasn't yours in the first place."
On Bedtime Stories, the Bad Girl makes her follow up appearance, but where she was scratching out the eyes of the world on Erotica, here - as on Love Tried To Welcome Me and Human Nature - she's licking her wounds.
Musically they're two pieces in opposition to each other - lush, cold and sorrowful versus unapologetic, unrepentant and still kicking - but it's somewhere in between these two extremes that mid nineties Madonna (and Rebel Heart Madonna) lives and breathes.
The Bjork penned Bedtime Stories may be hypnotic, but it's on Inside of Me, where M crafts a love song out of her grief for her mother that things are at their most surreal.
I don't consider Evita a Madonna album - even if it was like the foundation stone for her future. Instead, for me, ROL is the next M album up for consideration.
Adele recently labelled Ray of Light as the ultimate marker of post- maternity pop. Such is the uniformity and strength of the album tracks that many of them could've been hits.
Skin was as close to down and dirty as ROL got, and on Mer Girl, the mourning for Madonna senior is taken to haunting, Bell Jar levels.
But the most overlooked gem from the Ray of Light era wasn't anywhere to be found on the album - unless you were in Japan. Has To Be - the Japanese bonus track and title track
b-side is Drowned World but without the substitute for love. It's a warm, yoga meditation that makes no attempt to mask loneliness or accept responsibility like Love Tried to Welcome Me did and as such its the stripped back, blunt and vital M of old - just with Tibetan bells and whistles.
M's 90s music may not have had the impact her 80s music did, but it was much more interesting and varied, and, a giant leap forward creatively.