It's quite tough to pinpoint. She has managed to combine huge success in all formats with ironclad cultural impact in so many eras, even after suffering underperformances. LAP is an obvious first port of call because of the sheer magnitude of the lead single, but that would be 'only' 6 years into her career so maybe a little early. Then again, that's already longer than the average shelf life of 95% of mainstream female artists. She was definitely already an icon by this point though thanks to True Blue. Am I crazy to think it could be with Vogue? That song just remains completely ubiquitous and beloved in all circles despite it originating from a niche community. It doesn't just feel like the token summer dance craze hit either like say Macarena, Cha Cha Slide, Aserejé, Can't Touch This. It feel like a cultural touchstone. It's so often imitated never duplicated too. Going #1 for seven weeks with a single (not even the lead) from your 'damage control' album after the huge backlash she faced with Erotica makes Bedtime Stories also a legit contender imo. But then you come to ROL and it's simply the pinnacle of artistic evolution and bending the mainstream to your will, so that makes it almost too hard to ignore. But that feels too late somehow? ROL feels like an album made by someone who is already legendary and is just adding even more strings to her bow, not someone who suddenly levels up. I really think I'm gonna say Bedtime Stories tbh, defiance is synonymous with Madonna so I feel like it has to be a moment where she has already faced from tremendous pushback, and that era is the first time she recovered from that (and did it pretty spectacularly).
