Vogue Italia

Come to terms with her legacy? In case you haven't noticed, she's putting together her biopic. So she's revisiting her past in her own way, at her own pace and in the way she wants to do it. 
Moreover, I think she's actually been flirting with her legacy for a while, just not in a very obvious way (which is her right too). She often likes to reuse her old lyrics (like "Vogue" on "Holy Water", or even "Don't Tell Me" in "Future"), posts old photos on her IG, and I'm pretty sure Madame X is the closest she's been to embracing her own body of work. In fact, I remember she mentioned how she became her own muse while working on the album. Madame X was sort of a homage to her younger self, to her struggles in NYC pre-fame, and to the creative re-inventions throughout her career. 
Also, remember that Prince released very uncommercial and unconventional albums for many years, and also enjoyed the creative freedom and eccentricity that came along with them. Likewise, Geogre Michael always took a LONG time in between albums, and you didn't see anyone denying/doubting his standing in music. There is this strange expectation for women to keep up and to constantly demonstrate that they are at the top, that they are relevant. At this point even us, Madonna's hardcore fans, shouldn't even be questioning or worrying about her status in music history, or her relevance at all. She is actually a rarity in the music industry in terms of CREATIVE longevity. Cher has been around for ages but look at how many studio albums she released in the 2000s and 2010s. Also, while she relied on repetitive tour concepts and milked her catalogue like crazy (am I the only one who noticed how similar all of her shows are?), it's clear Madonna is far more interested in making new & innovative music, and to look ahead.
My call is for us to simply enjoy the fruits of her current work while she's still willing to release new music. She's clearly slowing down, after all. Madame X gave us some of the most amazing videos of her entire career and even if the MX Tour was a f-ing nightmare for many, it was truly a bold move on her behalf —artistically and conceptually speaking. People like Bob Dylan rarely look back  and release new studio albums like crazy and no one is questioning his legacy (also, he's a man, of course! Duh!). I'm a fan of Bob too and let me tell you, his concerts can be a nightmare in terms of his "mistreatment" of his own legacy—he reworks his old songs beyond recognition, and I think most of his fans are actually okay with that. Not the case for demanding M fans. They just want their diva to be stuck in the past with the same arrangements and giving them constant nostalgia. Which makes me think, people like Cyndi Lauper (one of my all time fave live performers, by the way) or Belinda Carlisle who sing the same 3-5 songs on every tour and with very little creativity behind the arrangements. So it's really frustrating how Madonna fans dismiss or underestimate her current work while whining too much about the past. We'll really miss it when she stops recording new material. That's for sure. 
Even if the 2010s saw M moving away from the centre of the pop music world, remember she always disliked being called a pop star. She preferred it far more to be called a performance artist, and maybe during the last few years, she took the opportunity to fully explore the depths of that. Furthermore, these "underperforming" albums still gave M 2 #1 albums in the USA in the 2010s, sold out tours, press and plenty of social commentary, which I'm sure will be better understood and embraced by future generations. 
Don't despair people! Enjoy the ride, one doesn't know when it could be over. Whether or not she gets another hit single again. 
 

Honestly, at this point I'd rather have her winning an Oscar for best original song for the biopic!
I'd also prefer a number 1 on Adult Contemporary Chart on her own that getting a Billboard no. 1 single by cheating and desperately having to use someone else's success. So humiliating.

Now, that's a though question. I really don't know. It would be great if it happened. But ever since American Life she has seemed much less focused (with Confessions being the exeption) Her last four albums may have some good stuff, but none of them has the magic that she once pocessed. 

From an objective standpoint, I'd pick
1. Madonna - The album that established her as primarily as a dance-pop artist, the most representative music genre throughout her career (Confessions On A Dance Floor, Hard Candy, MDNA, Like A Virgin, True Blue).

2. Like A Prayer - Her first conceptual album, when she officially became an "adult" artist and proved her abbility to tackle political and social themes through her work (Erotica, Bedtime Stories, American Life, Rebel Heart, Madame X).

3. Ray Of Light - The album that opened the doors for radical cutting-edge sonic experimentation and philosopical lyrical themes (Music, American Life, Madame X).