Speaking of lost projects a few pages back - the roles of Cristal and Nomi in Showgirls were first conceived for Madonna and Drew Barrymore.
I remember Paul Verhoeven saying he had one conversation with Drew about it, but she couldn't dance so her involvement was a non-starter. (She doesn't sing either - she was the only cast member in Everyone Says I Love You to have their vocals dubbed.)

Madonna doing Showgirls would have been kind of amazing. Granted, it took a good while to grow into a beloved cult classic from the disaster it was on release,'s not as if Madonna's reputation as a movie star could be hurt much more.
I'm revisiting all the singles she brought out in the acoustic slot during Rebel Heart. We were honestly spoiled in terms of setlist that tour, especially for those wanting the older stuff. Who's That Girl, Take A Bow, Drowned World, Secret, Crazy For You and more. Mad. Plus True Blue coming out of storage!
There's something heartening about these #JusticeFor[album] campaigns (except #Justice4ARTPOP which can choke), particularly coming from Mariah and Madonna's fanbases. It really shows you how deeply connected so many of us feel to the music and hopefully will introduce new listeners to pop history. It'd probably make more of an impact on Spotify rather than iTunes, but I don't care. It's great to see either way.
I’ve long thought about Madonna sitting down for some two-hour interview with a music news source that gets posted on YouTube, where they go album by album, talk about stories from the creation of certain songs, what she had in mind when she was crafting certain things, how concepts for tours and videos came together, deep cuts, a bit of everything.

And then at the end when she’s in that chair and can’t hide from it: “Madonna, whose d*ck do we have to hop on to get some special editions/Blond Ambition on video/etc?” There may be a ton of legal/financial reasons why this isn’t happening, but it would be interesting to see her address all of the ‘wish fulfillment’ stuff fans have discussed over the years.

She would respond "Mine, it's the biggest" and smile.
Fans: *get Bedtime Stories to #1 on iTunes*
Madonna: I have a special surprise for you all
Fans: !!!!!

Madonna: *announces new series of buffer scrubs for MDNA Skin

I've always seen an inevitable correlation between her being (seemingly) disconnected from her back catalogue and the way she's always looked ahead and reinvented herself throughout her career. I just can't imagine her sitting down to do a Mariah x Genius-like interview, not because she wouldn't know what to answer but because she probably just wouldn't care to do it. I'd love to be proven wrong obviously.