Madonna was one of the most popular entertainers of her generation. She just doesn’t have the talent to span multiple generations.
I wasn't even born during Madonna's debut and release of the sort of material girl pop she is iconic for...
I got to hear her growing up through her 90s / 00s artistic maturation, when she starred in Evita and won a Golden Globe...and with her newly trained voice - released "Ray of Light" at age 40, which to ME is her magnum opus both sonically and lyrically...It was so innovative for its time...and a major departure from her 80s days...

Loved that album. And I attended her "Confessions" tour in college.
She also directed an indie film about the Duchess of Windsor, Wallis Simpson, that nobody saw apparently LoL.
Anyway, i actually find her underrated as an artist...She self-sabotaged her credibility with a lot of her antics...